It’s often a big tripper’s dilema – what to pack for many places on a big trip in something we carry on our backs? What goes in that pack has to accomodate a large variety of places in terms of weather, activities, and culture. Tomorrow, I’m going on my fourth big trip and today I just finished packing. However, the act of packing was the only thing that happened in a day.  I’ve been considering this dilema and my list for several weeks now as I shopped and planned my trip for two weeks in Italy and two weeks in Africa – one week for a cultural tour in Ethiopia and a week of safari in Kenya.  I really wanted all of what I was buying to fit in carry-on luggage too, which limits me to a small bag no more than 22 inches in length.

In Italy, I’m going to be in Milan and Florence – two very fashionable cities. Then, I am visiting Tuscany and staying at an working farm agriturismo and finally hitting up the beach in Sardinia. This means I need clothes that are comfortable and look a little on the chicer side. In Africa, I’m visiting the cities of Addis Abba and Nairobi, going on walks through mountains and bush, and visiting religious archeological sites.  I need rugged and durable clothing that covers the majority of my body and can be layered. The weather in both places for May range from moderate (50/60s F) to warm (70s/80s F) but not jungle-hot or monsoon-rainy. I’m also a bit of a klutz so need to bring my big bad hiking shoes, which are about half my suitcase in size.  Packing felt like quite the challenge.

The Pack

I decided on an Osprey Travel Trek Waypoint 40L pack because it’s a carry on size, is a neat line – meaning not a lot of straps all over the place, and very light (3lbs).

The Packing List

Here’s my packing list, I did a dry run with everything to make sure it fit, and used  3 Eagle Creek packing cubes to fit all in. I’m also bringing my regular purse, which is a medium-sized purse that can fit my iPad and books for the plane. I did the majority of my  shopping at Old Navy, REI, and Macy’s.

Clothing & Shoes

Two lightweight, long sleeve button down shirts – one Old Navy brand and one REI’s Larch shirt (unfortunate name, but great shirt!)

Four short sleeve shirts – mix of brands, but all cotton

2 tank tops - mix of brands, but all cotton

2 dresses that don’t wrinkle (Italy)

1 lightweight waterproof, windproof jacket with fleece lining from REI

2 pairs hiking pants – one from Northface and one from REI

1 pair cotton leggings

8 pairs of underwear, 3 bras

3 pairs of socks, mix of cotton and marino wool

1 pair Merrel hiking shoes

1 pair comfortable and stylish walking shoes (am giving these Arcopedico’s a try)

1 pair Chacos flip-flops

1 pair stylish wedges (they take up so much space, but are so cute and go with the dressses)

1 light swimsuit cover up

1 sarong and 1 swimsuit

Electronics

iPad + Logitech keyboard + case

Canon 110s Point and Shoot camer + case

iPhone to be used as iPod and only when there’s wifi

Nikon D5000 DSLR camera

Amazon Kindle- Paperwhite + cover

All chargers and two converters

1 DK Florence and Tuscany Guidebook (this is the only book!)

Accessories

Travel wallet by Sherpani

Secure wallet by Rick Steves

Headlamp

Flashlight

Bandana (with first-aid instructions compliments of my Dad)

World map and postcards of California

Toiletries (too many to list, but it’s all around daily care and then first aid). Definitely getting bug spray with deet for Africa.

Hat and sunglasses

How it will go? We shall see. I’ve traveled with more for weekend trips. The good news, I can (and do!) always buy stuff in country and I can ship souvenirs home. Either way, I’ve packed a pack full of items that will work for two types of trips in one jaunt and that I can carry and possibly run to catch a train with. We’ll see on that last one, but here’s hoping.

It started with a question in a dark bar. Over manhattans and margaritas, at a friend’s birthday happy hour, my friend A and I were talking about traveling. Her last international big trip was to Australia in 2011 with a group of friends, mine was to Peru in September. A few days before this conversation, I was trying to answer the question, “How did I want to travel?” After Peru, I knew that a group tour wasn’t for me and I’ve done the solo thing.  I had found a fun, solid group of friends in San Francisco and thought  – I’d really like to travel with my friends.

After sharing past stories, we paused and I can’t remember who brought it up, but we shared, “What do you think about going somewhere together this spring?” which led to “where do you want to go?” and then “have you ever been to Italy?” I had only been for three days in Rome in 2010 and thought – that’d be a great place to travel with friends – Europe is relatively easy and safe, not too much culture shock to wade through so we can have fun and soak in the days. A had been there before with her family and when I said, “I’d really like to go to Florence,” she squealed “I looooooooove Florence!” And so the idea was born: Florence, and Tuscany sometime in April or May. Sardinia was added to the itinerary when I realized I needed some beach time and we both had two weeks of vacation to use versus one.

This post is about the evolution of our trip: how we are planning a trip to Italy, specifically an Italian itinerary of Milan, Florence, Tuscany, and Sardinia for two weeks.

Finding Inspiration

Now that we knew where we wanted to go, what did our trip look like? What did we all want to do? As soon as we decided on our main destinations, I started to collect ideas. We knew that we wanted to see the big sites in Florence, especially the Uffizi Gallery.

I wasn’t convinced about spending too much time in Milan. I knew about the city from various Fashion Week headlines, but the city never came with the same breathiness from travelers when they talked Rome, Venice, or Florence. A call to my best friend B, who lives in Europe, resolved any worries. She considered Milan to be a city that was perfect for seeing how Italians lived – that it was very easy to get off the tourist path and frequent the same restaurants and shops that Italians went to. That’s not the easiest thing to do in tourist-soaked Rome.

I searched my own magazine library and found the National Geographic Traveler cover story on the Heart of Milan and I was convinced that we needed to see more of it than the airport.

In Tuscany, I wanted to sit on a patio with a bottle of Chianti and watch the setting sun over vineyards and olive groves. I wanted to eat under a trellis with A and fellow travelers, passing bottles of locally grown olive oil and plates of salty pasta and roast vegetables. I had heard of renting villas in Tuscany, but our budget was more farmhouses – and I was introduced to the wonderful world of the agriturismos. These are working farmhouses throughout Italy that have been converted into pensions and apartments for guests.   They have swimming pools, kitchens, and those trellised patios with high views.

And then, to get us extra excited, I started an AFAR Wanderlist on Tuscany Road Trip and a Pinterest Board to collect ideas and inspiration on what to do and where to eat.

Trip Dreaming Tips

• Talk to people who have been there
• Go online to travel communities like AFAR Media and Pinterest to start collecting desired places
• Pick up travel magazines and coffee table books to start seeing where you’re thinking of going

Deciding Where and When to Go

We went from dreaming to planning over bottomless mimosas. One might think that this is not conducive to a sound itinerary, but it is. Over brunch, we talked openly about the places and activities that could make up our trip. Then, we started to map out the trip. We referred to the maps in the Lonely Planet guidebook and Google Maps on our Smart phones to estimate distances. A train from Milan to Florence looked like the best option. Lucca was in, but then it was out because it was too far for too short of time. We settled on looking at an agriturismo near Siena and touring to the south of Florence. Then, I brought up the idea of Sardinia for the last week and A found a ferry service that would get us from Livorno to the island.

I wrote out the days roughly in my Moleskine to layout the trip. Since we didn’t know the exact dates yet, I numbered the list by days – 1,2,3…to 10 and then the place next to it. This method established our pace.  The trip took shape.

After the brunch session, A and I g-chatted about dates, checked with our bosses, and reviewed plane schedules. I had miles to use and A had a trip credit. We had to use United, but checked to see if the prices were competitive by using Kayak.com. I booked online through the rewards site and A called a very helpful customer service agent who made sure we were on the same flight.

Trip Planning Tips:

• Refer to maps and a good guidebook
• Layout the trip by days to estimate pace and duration
• Collaborate on dates and places that work for all travelers
• Check Kayak.com to compare prices, but book directly with the airline

Arranging Lodging and Transportation

It was time to start our itinerary and get to down to laying out the exact trip. I borrowed an itinerary format I had seen used on group trips before: lay out the dates and consider the transit time and keep track of lodging, confirmation numbers, and days of travel.

I set up a shared Google spreadsheet with eight columns: Day, Date, Description, Lodging, Transportation,K Money Down, A Money Down, and Confirmation Numbers. The rows go day by day and describe what we are doing, where we are staying, and how we are getting there. Once we started to get the details arranged, A set up a trip in Tripit so we can have the itinerary information on our smartphones through the app. We also kept track of any money we were each putting money down on hotels and transport that we would split up later.

We divided the tasks: A took Milan and Florence and I took Tuscany and Sardinia.

Lodging: We used booking.com, agriturismo.net, and Wimdu.com. Booking.com has reviews like Trip Advisor so we could get a sense of the place.  Agriturismo.net is a huge site of all the agriturismos in Italy. It shows pictures, reviews, activities, and extensive filtering. The site has nice feature where after I contacted one agriturismo, the site asked me if I’d like to be contacted by places that meet the criteria. I said yes and soon I was getting emails from lodge owners saying that they had space for me. Several days later, I had a confirmation.  Wimdu.com is like Airbnb.com, but in Europe. They had an extensive inventory of apartments in Sardinia and booking was simple – I found the place, inquired for the dates, and was approved.

Transportation: We had a variety of planes, trains, and automobiles to book. For Milan to Florence, we used Italiarail for train travel. A booked the car through American Express Travel because she used them through her work. If we had to book on our own, I found this very helpful article on how to rent a car in Europe. Then, I researched ferry services and found Corsica Ferries to get from Livorno to Sardinia overnight. The majority of our entire trip budget is going to the rental cars, but we are short on time and it’s the easiest way to get around.

Tips:

• If you can, use a variety of resources – ask your boss if you can use resources through your company to save money on travel.
• Never e-mail your credit card or bank details to anyone – email is unsecured. A had to fax a copy of her credit card and I sent a wire transfer via the official instructions on the booking site for only 20% of the final price.
• Europe has many budget airlines that can be cheaper than trains or rental cars.
• If a trip is going to take more than 7 hours, consider taking an overnight train or ferry to money  – it saves on hotel costs and a day of travel.

Typically,  it’s lodging and transportation that I only book in advance, but the Uffizi and the Michelangelo’s David require reservations far in advance, so I booked these tickets two months in advance

The Itinerary:

We leave in a month, have the skeleton of our trip booked, and are going to see these beautiful places in Italy.

• Day 1: Arrive in Milan and settle in, night in Milan
• Day 2: Tour Milan, specifically the Doumo and the Galleria Vittoro
• Day 3: Leave Milan via train to Florence, night in Florence
• Day 4:  First day in Florence and a visit to the Uffizi Gallery reserved in the morning
• Day 5: Visit to the David in the morning
• Day 6: Pick up rental car and head to Siena, Tuscany
• Days 6-9: We are going to ask around and find what towns to hit, but also chill around the agriturismo and do some bike riding
• Day 9: Leave Tuscany, return car to Florence, and take a train to Livorno. At night we depart for an overnight journey to Sardinia
• Day 10-13: Sardinia
• Day 14: Fly Easyjet back to Milan and then onwards!

What to do?

To help fill in the gaps of where to go and what to do while we are there, I’ll be collecting more information and tips and connecting with other travelers. Here are my starter wanderlists…

• Where to Eat in Florence
• Two Days in Milan
• Reviewing the Q&A on the must dos 

I’m also taking along my favorite series of guidebook: DK Eyewitness Travel Guide: Florence and Tuscany. I love these books because  they have pictures and details explaining the major sites and neighborhoods. Their food and drink sections show an overview of local specialities (with pictures). I find it much more helpful in country than lists because I can visualize what I’m going to experience.

Overall, since that conversation in the dark bar, this trip has taken about a month in duration to plan and about 5 hours of effort for each of us. Now that the Italy trip is in view, I’m back to the dreaming phase of all we are going to see and do!

Photocredits: Photo by MojoBaron on Flickr

I was skimming The New Yorker and saw a review of the book, A Sense of Direction by Gideon Lewis-Kraus. The review mentioned that the author went on three pilgrimages: the Camino de Santiago in Spain, the Shikoku pilgrimage in Japan, and the Rebbe Nachman of Breslov pilgrimage in the Ukraine. I paused at the description and added it to “my books to read” list. Pilgrimages are a popular activity for Big Trippers and something I’ve always wanted to do myself for precisely the reasons that Lewis-Krause shares in his book: to separate myself from daily life, to create space and stillness, and to meet other pilgrims.

The book begins in Tallinn, Estonia where Lewis-Krauss meets up with his friend and future-fellow pilgrim Tom. Lewis-Kraus can’t remember it, but he agreed to hike the Camino with his friend after a night out partying. Back in Berlin and remembering the commitment, the author describes his distraction-full, but directionless-life. He moved to Berlin from San Francisco thinking “I’d been living in lovely provincial San Francisco and had moved to Berlin because I’d felt I was missing out on something exciting, and now I was on the brink of leaving lively, provisional Berlin because I was afraid of mission out on something serious.”

With Tom, who is on the verge of settling down into a relationship, he starts the Camino, his first of three pilgrimages. On the route, he meets a Japanese couple who tells him about the Shikoku pilgrimage and that it’s “very hard but maybe you try someday,” After the Camino, Lewis-Krause commits to Shikoku, Japan as his second trip, circumnavigating the island by walking to 88 temples. Finally, Lewis-Kraus embarks on the third faith-based pilgrimage to the Ukraine with his brother and father to resolve long-standing family issues. On each journey, there are characters, trials, and lessons. The pilgrimages are the stage for the author’s finding clarity, strength, and compassion for himself and his family.

Here are some quotations from the book that revealed to me the many facets of a pilgrimage. Overall,  I highly recommend this book. It’s not just the journeys that are very interesting, but Gideon-Kraus is hilarious and real. There are parts that read like a dissertation, but I took the time to dissect the complex thoughts and loved the elegant insights about life revealed through the analysis.

The Reason to Do a Pilgrimage

“The pilgrim could step outside of all roles and just be a person, someone without responsibilities or expectations or any constraint besides continuous forward movement to a distant goal.”

“[In religious life] Actions are justified because you are commanded to do them, and commanded by somebody or other who’s got a plan. Secular pilgrimage is a little vacation into that sort of plan, but the thing about that vacation it that it has very little to say about what happens next. What it can do is show you that the line between obligation and desire is rarely clear, that what we often label obligations are really desires, and that each step forward is some blurry function of choice and necessity. It can suggest that there might, in the end, not be so great a difference between saying “I felt like it” and “I had to.”

On Meeting and Walking with Other Pilgrims

“I also think it has to do with the fact that we’ve come to share this experience with all these other people – Tim and David and everybody – that I think we’re sorta happily stuck with from here on out. They might be a bunch of crackpots and buffoons, but so are we, and I feel some new sense of belonging, of responsibility.” – This is a quote from fell0w pilgrim, Tom

“We’ve all come together so effortlessly, and we all see to feel so fit and so vital, so warm with roaring blood, so similar in stride and gentle in conversation. We pause for a moment, and when we continue, we do it wordlessly.”

On Walking Alone

“The one time I’ve proposed being alone was right when Tom was criticizing me, accurately, for being unsympathetic to his needs and his pain. All along I’d had such a romantic idea of what it would mean to be alone –  how heroic it would be to do this without any diversion or any support from anybody at all – but now I see it as the desire to be able to walk away. To Buen Camino. As an evasion. As an attempt to get away from my close friend right when he’s called me out for being selfish and stubborn and uncaring. An opportunity to meet some strangers, people who won’t know that I’m selfish and stubborn and uncaring. Maybe my desire to be alone is my desire to preserve some image of myself that I know won’t stand up to Tom’s sustained attention.”

On Receiving Help From Locals

“Most accounts I’ve read talk about the osettai custom in terms of the pilgrim’s experience: This walk is equal parts hardship and exactly what JR’s referring to: the gracious, humbling acceptance of support. The one exception I’ll come across is an academic study of the pigrimage by a Manchester professor called Ian Reader, who writes, of osettai, that it’s the patent neediness of pilgrims that allows the locals to rise to the occasion, to be their best, most generous selves.

On How the Pilgrimage Makes The Pilgrim More Focused…

“I’ve noticed that I’m especially able to focus on work despite the noise and my physical exhaustion. I can spend two hours writing up my notes rom the day – in anticipation, of course, of the next email dispatch – without looking up once; I’m more productive in the two hours between four and six p.m. on the Camino than I ever was in an entire week in Berlin.”

…And Quieting the Mind

“Even when I can’t fall asleep right away, I don’t mind just lying there. There are so many things I find I don’t think about at all, like what’s going on at that moment anywhere else. All were doing is walking and then stopping, but somehow that sense of structure and organization affords me so much productivity and calm.”

On What A Pilgrimage is Really Like

A fellow pilgrim shared, “There are so many books in Germany on this [Camino], but nobody mentions the pain! Maybe it is because afterward, when you get back to your real life, you remember only the good parts.”

In response to a fellow pigrim  stating he wouldn’t get any more out of walking. “Right, but that’s precisely when it gets the hardest.  Right when you feel like it’s no longer hard, because the hard parts kept it from being truly hard, you know? That’s what so much of what this was about for me, at least in the end; continuing to walk when both the discomfort and the novelty have passed. Like, I don’t know, a long-term relationship.”

Helpful Links:

• Sense of Direction by Gideon Lewis-Kraus on Amazon or better yet, buy it at your local bookstore.
• Camino de Santiago FAQs by Sherry Ott, who walked in 2012 and blogged about the practical side of the trail.
• Lonely Planet’s Guide to the Shikoku 
• The Wikipedia entry on Rebbe Nachman
• Trek-Worthy Trips as an AFAR Wanderlist

Happy trails!

Photo credit: Photo by ramkarthikblogger on Flickr

Lavinia Spalding, overall inspiring writer and editor of Best Women’s Travel Writing Vol 8, sent an email out to her contributors. After I read it, I wanted to share. The seven tips by writer Laura Fraser summarized most of what I learned about travel writing in courses, conferences, and books.

Personally, I know these tips are tried and true. Laura taught a “Getting Published” writing class at the Writer’s Grotto that I took last year. It was out of that class that I refined “Coloring Within The Lines” about my time volunteering with Mother Teresa Charities, which was selected by the Bay Area Travel Writer’s as a part of the Stories From Around The Globe anthology. Laura’s help and editorial eye made sure that my story was focused and impactful.

I saw Lavinia’s email a few days ago and thought Laura’s travel writing tips would be very helpful to the travelers who want to tell stories from their Big Trips in a meaningful and publishable way. These tips are posted with permission.

Lavinia’s Intro:

Laura Fraser–a NYT-bestselling author, Italophile, contributor to Best Women’s Travel Writing, and writing teacher–is holding an intimate workshop in Italy this May 4-11 to hone your travel writing, personal essays, and memoirs, and have some amazing culinary adventures.

I asked Laura if she would share some of her travel writing tips, since she has reported from Rwanda, Samoa, Mexico, Italy, Chile, Australia, and other far-flung places, many of which she wrote about in her memoir All Over the Map.

Laura’s Travel Writing Tips

I always travel with a camera and take a lot of photos. Sometimes they get published, but more often they give me details I might forget, like a visual journal.

Speaking of journals, I always keep one. One of my biggest pleasures while traveling is to sit in a café and write in my journal.

Be curious and friendly. Some of my best stories have come from meeting locals and chatting with them. I’ve ended up on a 5-day camel safari in the Sinai, learning how to make the best risotto in Italy, and visiting Sardinia’s Alcatraz all by just asking locals about their lives.

Always remember that you’re looking for a story, not just describing a place. Stories usually come from the people you meet there, whether local shopkeepers, chefs, ethnomusicologists, historians, or scientists.

Remember that when you pitch and write a travel piece, it can’t just be a destination. The question is always, what about Patagonia? (How is the Torres del Paine National Park recovering after the fire). What about Florence? (What if we looked at it through the eyes of George Eliot and her book Romola). What about Cuba? (What’s it like to take a salsa dance tour?).

Pack light. I always take only a carry-on. I mainly pack black, unless it’s the tropics, with accessories (scarves!) to liven things up. Bring comfortable shoes and some little black flats for dress-up. If I’m traveling to Third World countries I usually take clothes I would otherwise give to the Goodwill and leave them there when I’m done with them, shedding them along the way.

Write your story as soon as you get home, while it’s fresh. You may not sell it then, but get it down.

Be mindful of your safety while you’re having adventures. Don’t drink too much with people you don’t know. Always know your way home and have some extra cash in your pocket to take care of yourself. Be careful where you walk alone.

Here’s some information about her Italian Writing Affair workshop May 4-11:

Come to Umbria for a writing workshop–and a taste of la bella vita–with NYT-bestselling author and Italophile Laura Fraser and culinary expert Kris Rudolph. Spend a week writing and exploring farm-to-table cuisine, staying in a 17th-century stone villa amidst rolling hills on an organic farm. Eat, explore, and write to your heart’s content.  Excursions include dining at the best regional trattorias, exploring local villages and the farmers’ market, visiting a winery, going truffle hunting, and spending a day in the town of Assisi. The writing workshop is intimate (maximum ten), for all levels, with a focus on writing from experience (personal essays, memoir, travel, family history).

Learn more about the Italian Writing Affair workshop>

or e-mail Laura for more information or to register at: info@laurafraser.com.

–

Photo credit: Photo by Walt Stoneburner on Flickr

Photo Credit: Photo on Flickr by Carole Mage

At a travel panel  last summer, a couple came up to me afterwards and asked me questions about how I did my own big trip, specifically on my work.

“What did you do with your job?” Well, I had to quit it to take the first big trip. It was a point of transition and I didn’t want to move onto my next role, so I left.

“What did you do for money?” When I came back, I found a consulting job and lived very minimally until I saved enough and then went out again.

The couple explained that they wanted to go to the Americas for a year, but seemed to be afraid of finding employment when they returned. They were journalists and so I gave them advice on how keep their skills marketable while they were gone. Afterwards, I was talking with a friend who had witnessed the exchange. “What they heck are they worried about? Go off to Mexico, sit on the beach, write stories about the people they meet, don’t worry about what’s going to happen when they get back!!”

I agreed because it really does all work out upon returning,  but their questions and fears were very common among future travelers I meet.

In following travel blogs and writing my own, meeting future and returned Big Trippers, and reflecting on my own experiences for the past five years, there is one theme that comes through continuously. It’s a theme found in posts, comments, emails, raised hands, and conversations around these questions:

• “how do I tell my boss I’m quitting?”
• “how do I quit my job and travel the world?”
• “what happens to my career?”
• “how do I pay for it?”
• “how do I do it?”
• “where do I go? when?”
• “what do I pack?”

World travelers are asking these questions to research their trip and see if world travel is right for them and that’s great, gather as much information as you need and go. But underlying a lot of these questions I’ve found is an undercurrent of fear – the fear of the unknown and fear of making the wrong decisions.

In our stationary, non-travel lives we live by predictability and routine. For a working professional, it’s a life of corporate ladders, Outlook calendars, meeting notes, and grids.  It’s bucks direct deposited every two weeks. It’s accrued PTO and a sacred health insurance card in our wallet. Outside of work, it’s scheduled family time, friend time, gym time, and time to relax. There is comfort in the structure and predictability.  The desire to long-term travel shakes that structure a bit. It asks, what if I left all that to see the world and live my travel dreams?

And  if you decide to answer that question with, “You know, I’d really like to do that.” and start asking How? a new foundation is built. With each Google search, question asked, event attended, and book read, the foundation to a new path and way of life starts to get stronger and the previous structure starts to grow a few vines from neglect. It’s not as attractive anymore.

But at every step forward, fear of the unknown is peaking its head in and can make one struggle to get past the rational understanding that “yes, people say I can do this,” to the actual belief of “I can do it. I will do it.” In service of  getting you from where you are now to enjoying your brilliant Big Trip, let me share with you three pieces of advice that will help you deal with this fear of the unknown. You won’t know if this advice is sound until you actually try it. So please, go out and try it.

Things On the Road Will Not Go According to Plan And That’s More than OK

“I have an hour before my ferry leaves the port of Souda, taking me away from Crete and back to mainland Greece. If I don’t hit that ferry, my carefully engineered schedule slithers through my fingers and I’m left untethered, without local knowledge, a decent enough grasp of spoken Greek or the money for new tickets. Without that ferry, I’m lost.

- Mike Snowden “Lost And Found: How Uncertainty Makes Travel Memorable”

On the Road, Wherever You Are Is Where You Are Supposed to Be

World traveler Robin Esrock talks about how he took his big trip and dealt with decisions and experiences along his journey.

Your Career Will Not Enter a Black Hole Never to Be Found Again If You Travel

“While you believe you are embarking on an amazing, life-changing experience, you aren’t so sure potential employers will view your break with such enthusiasm. Indeed, you may be afraid that your time off will hurt you more than it will help you…Based on my experience, there are 10 things you can do before, during and after your trip to maximize your chances of finding the job you want after you return.”

- by Katie Aune in “How to Return to the Workforce After Quitting Your Job to Travel.”

I found this piece a very well thought out, true, and helpful article that can get you past that fear of the unknown about your career if you take a Big Trip.

I hope this helps a bit my future Big Trippers. 

Recently, I received this email from a reader of my blog. I think a lot of points are relevant to big trippers as this young person considers his future. Letter reprinted with permission.

——

“I’ve just recently started to think about colleges I want to attend, as going to college is just what is expected of me. However, when I was talking to an adult at school about how I’d like to travel some day, she seemed very excited for me. She was the one to give me the idea of not spending so much money on college and to go straight to wandering the world. Now, my parents are pretty lenient but I’m sure they’ll advise me to go to college any way. I’m wondering if you, an experienced traveller, would recomend one or the other.”

Here was my answer:

Thanks so much for writing, happy to give some thoughts on what you ask. Congrats to you for asking these questions – huge questions! Important questions!

First, I wholeheartedly believe that you should go to college. I don’t know you, but a college degree is an investment you make that pays off huge in the future. Not just financially, but professionally and personally. The degree gives you freedom and the college experience, maturity and skills in critical thinking, analysis, communication, teamwork, leadership, etc. Once you get a degree, even in a humanities field, it’s up to you to make something of it. However, you have a very solid foundation that others, without degrees, do not. Financially, I don’t believe one should get into huge amounts of debt.

Anyway, onto the travel questions: I believe that there are a few ways to travel and mix college.  A disclaimer: This is broad advice, you and your parents know your situation the best. Plus, you haven’t mentioned what kind of experience you have traveling thus far or where you want to do. These are important factors.

The first questions are: Where Do You Want To Go? What Do You Want To Do?

Sit with this one. This is the formation of your travels. I wrote a blog post about creating your travel vision. It may be a little Oprah for you, but this method helps me.

This post is a guest post by Rachel Stern, who was a speaker on working while abroad at the 2012 Meet Plan Go San Francisco event.

For some, travel is a prime opportunity to flee the day-to-day demands of work. Yet for others, working while traveling or living abroad can not only be a way to finance and prolong big trips, but the very core of them. Working in a new environment, often in a new language, is a prime way to bolster cross-cultural skills, polish a CV, and above all have an unforgettable experience.

Below are some tips on how to find work abroad, whether as an assemblage of odd jobs or a longer position in a specific locale.

Embracing Odd Jobs, and How to Find ‘Em

A number of big cities around the world, and sometimes countries as a whole, boast an English language publication, which often advertises a slew of jobs. The Local, for example, has editions in a handful of European countries, and lists available positions on its homepage. Don’t see what you want listed? Reach out yourself. Ask around at local events, and post signs offering your skills.

When I was living in Sweden for five months, I tacked up a flyer at a nearby university offering help editing papers in English, and received a number of responses. Also capitalize on your skills. If you are a hairdresser, for example, cut hair at hostels, or if you are an artist, consider creative ways to utilize your talents. At one music festival in Buenos Aires, I met a Canadian woman who set up an impromptu face painting booth, and received a long line of kids and adults alike. Look also into seasonal work, such as WWOOFing on farms around the world, or working at a resort. InterExchange is a great resource for temporary jobs in Australia and New Zealand.

Fulbright and Teaching English Abroad

A lot of people are familiar with Fulbright grants just for study, but there are just as many opportunities through the program for research or teaching English abroad. Countries such as Argentina and Spain are flooded with applicants, so if you are not set on one specific place, you may want to consider someplace “off the beaten path” such as Latvia, where this past year there were 0 applications for one spot available. Compare this to Spain where there were 400 applications for 68 spots.

Check out the language departments of universities and community colleges and government websites. Often U.S. embassies around the world will maintain a listing of English teaching jobs and fellowships, but you can also contact them. GoAbroad.com also maintains a comprehensive listing of teaching jobs.

Transferring Within Your Own Company

If you work for an international company, consider asking to be transferred. A lot of companies do not openly advertise these jobs when they open a new office, but rather rely on word of mouth referrals. Reach out to the office where you would like to work to inquire about available opportunities. At the very least, you can be on their radar for when a job does open up.

Being an Entrepreneur

Create an opportunity when it’s not readily apparent. Set yourself apart: In most areas of the world, being a native English speaker is already an asset. Look for areas where the field you are in is expanding, and see what niche you can fill. Learn the local language, or improve your skills in it, before you go. You may be able to get by in a new country without the language, but for longer-term endeavors, having skills in the local tongue demonstrates your dedication to, and understanding, of the place.

Take cues from the successes of others who have successfully launched a company abroad. American expat David English combined his love for wine and Argentina, opening a business in mountainous Mendoza. He details his successes and those of other entrepreneurs he meets in Expatriate Entrepreneurs in Emerging Markets: Ten Success Stories from Argentina, published last year. Go to American Chamber of Commerce events in your new city to network and meet like-minded folks. For more information, Entrepreneur.com offers an excellent lay-out of how to launch a company in a foreign land.

Kristin note: Long-term traveler Lee O’brien write this post on starting a business abroad.

Other Opportunities

World Nomads maintains a comprehensive list of travel scholarships around the world. Look for the ones that resonate the most strongly with you, and apply. I have been abroad on a number of such travel grants over the past few years, and often hear the following sentiment: “I wanted to apply but it seemed too competitive.” Remember that there are often less people submitting applications than you think — maybe because they’re thinking the same thing!

Strike a Balance of Work and Travel

You’re heading to a cool new locale for work. Take the time to actually enjoy it and get settled before plunging into a full-time job. Arrive a few weeks early, step away from your emails, and explore your surroundings. Check out Couchsurfing.org and Meetup.com for free venues to mingle with locals and travelers alike — and as an added plus often brush up your language skills in the process. Have fun — you may forget you are working!

About Rachel:
Rachel Stern is a Bay Area-based journalist and travel writer. Her reporting projects have taken her around the globe, from Buenos Aires to Berlin. She just returned from a 2.5 month sabbatical in the latter, penning stories from throughout the country for prominent European and U.S. media outlets and failing to master German grammar. She’s been a big proponent of solo-travel since 2007, when she extended a plane ticket from a two-week volunteering trip in Argentina on a whim, spending several weeks backpacking in Patagonia. She chronicles her travel adventures and advice on a Huffington Post blog, and hopes to encourage people to pursue their travel ideas, no matter how “unrealistic” they initially appear.

Website: Rachel Stern on HuffPo

After my first big trip in 2008, I called a psychic. Referred to me by my sister, she had a good reputation of doing readings. I don’t usually rely on otherworldly advice, but it was a time of need. I called her because I had just returned from a trip that changed my life and I wanted more of that transformational nectar. I wasn’t sure how to go about it.  My savings were gone and, being the depths of the recession in winter 2009, there were no job prospects  to fund any future trips.  The future was, what I call, “the big gray.” Formless and pathless, the only point on the horizon was that I knew I had to travel again.

Sitting alone in my bedroom in the tundra of Northern Wisconsin, I asked the psychic the basic question to clear the fog, “What does my future hold?” She said, “You’re going to teach other people how to do what you’ve done… how to travel…” This statement felt right. I knew this is what I was going to do. Again, no idea how or when, but I felt this truth in my gut.

Four years, two more big trips, this blog, and a life in San Francisco later, I’ve done just that. On October 16, I hosted an evening of about 120 travelers, two keynote speakers, three panelists, five volunteers, and 12 breakout session speakers at Meet Plan Go – San Francisco.  Meet Plan Go is a national organization that believes the same thing I learned on my big trips – life isn’t lived in a cubicle and long-term travel makes you a better person.

I got involved with Meet Plan Go slowly, first as a panelist in 2011 and then running quarterly events on volunteering and budgeting with co-founder Sherry Ott and Traveling Philosopher Spencer Spellman. Early last spring, Sherry asked me to host this year’s annual event. It was a bigger task – Meet Plan Go was changing format and we were taking it from the inspirational to the practical, arming travelers with the tools they needed to take their own big trip.

On the big night, 120 dreamers, rookies, and veteran travelers arrived to learn about how to plan their big trip. And my event was just the San Francisco event – almost 1000 people total learned how to take a career sabbatical and travel long term at events across North America.

Me kicking off the event. Photo by Mark Altenberg

My goal for the event was to inspire with stories and aspirational speakers and then move to the practical with a panel and then individual breakout sessions – giving travelers advice and resources to plan their own big trip. I assembled an amazing cast of speakers to do so – every one had their own story of how travel affected their life, unique big trips and sabbaticals, and advice to share.

Survey results are forthcoming, but overall I felt the event a big success. I heard from attendees, speakers, and volunteers that Meet Plan Go – San Francisco was a great event and helped people feel inspired and ready to long-term travel. And we raised over $1000 for the AFAR Foundation and the Learning AFAR program.

Speaker Fran Wickner shared this with me a few days after the event, “I had invited a friend to the event who was planning to go to Asia at some point in the near future for an extended trip. He had been saving/thinking/talking about it for a while, but couldn’t JUST DO IT.   I saw him the evening after MPG and this is was he told me:  ”I was so inspired by the speakers and the other people I talked to, that today I told my boss I was leaving on November 26th and didn’t know how long I will be gone, I gave notice to my landlord so now I don’t have the expense of rent when I’m gone, and bought a one way plane ticket leaving December 1st.”

Speaker Britt- Marie Alm’s breakout session. Photo by Mark Altenberg

Thank you to every one involved and thank you to the attendees and travelers for making the event a success.

Below is a list of links related to the event, including advice from the speakers on their topics.

Introduction

• The Story of My Big Trips: Kristin Zibell
• Meet Plan Go Organization
• Andrew McCarthy’s Big Trips
• AFAR Foundation

Keynote Speakers

• Jeff Greenwald’s web site and stories
• Don George’s article on Paris in National Geographic Traveler

Panelists

• Francis Tapon’s travel advice
• Ted Beatie’s travels in Southeast Asia
• Kelly Wetherington’s travels around the world

Breakout Session Speakers

• Itinerary Planning by Robin Devaux
• Itinerary Not Planning by Kelly Wetherington
• Budgeting by Pierre Devaux
• How to Travel Local by Fran Wickner
• How to Make Money While Living Abroad by Spencer Spellman
• 6 Ways Taking a Big Trip Changes Your Life
• All the event pictures on Facebook

Guest Post By Fran Wickner, Ph.D., MFT, speaker at 2012 Meet Plan Go San Francisco on October 16, 2012.

Round The World Travel (RTW) works well for some people on a career career sabbatical,  but being able to “Go Local” by staying in one place is another excellent option for those taking career breaks.  Staying in one place for a period of time (vs RTW travel) allows for a slower, deeper form of travel.  You learn how the locals live, how life in your adopted town ebbs and flows.  It doesn’t mean you won’t travel, you can take great day trips (or short mini vacations) from your home base.  It’s like the best of both worlds:  traveling and then returning to the comfort of your “home”.

Living local let’s you experience life like the people who live there, eating in the cafes they go to, shopping in the stores they shop in, hanging out where they hang out, and in my case (living in Cinque Terre, Italy) going on the breathe-taking hikes that the tourists don’t have time for when they only come for a few days.

This article will help you learn how to get a local cultural experience vs just a tourist experience, how to meet and make friends with the locals and why renting an apartment in a non-tourist section of town is conducive to this.

1.Learn the language

Before you leave is a good time to start; you can go to classes at a local Adult Education program, a language school, or get some language tapes at your library.

Then, when you arrive at your destination, find someone to trade English and the local language with. My language partner helped me meet lots of his friends.  If there is a language school nearby, take some classes.

Even if you are going to a place where many of the people know English, still learn some of the language.  When I lived in Denmark for a year, the Danes were so happy that I took the time to learn their language that I made many more friends than I would have speaking only English (and no excuse that “all Danes speak English”. They loved that I would try to talk in their native tongue).

2. Before You Leave, Learn about the Culture

Read books both fiction and non-fiction.  Go to events in your area before you leave that are sponsored by that culture.  Watch movies.  Talk to people from that country.

Note from Kristin: I really like Goodreads for book recommendations on a place and then Lonely Planet’s lists in their guidebook on what to read and see before going.

Then, when you are there, follow the local culture rules and customs. Where I lived in Italy, the townspeople did everything they could to not stand out, and I followed that, too.  In Denmark, the Danes are not pushy, they don’t brag, their supermarkets tend to be quiet, people wait in line. So when I lived there and then visited recently again, I made sure I followed the customs.

3. Rent an apartment

Live where the locals live, not where the tourist section is.   You will be treated like a visitor, not a tourist.  You’ll be part of the real life of the townspeople rather seeing what the tourists are doing.

To rent an apartment, I recommend Google “vacation rentals” and look on sites like Trip Advisor.  Then negotiate a rate based on your longer stay. The woman I rented from lowered the rate because I rented in advance and paid most of the rent up front, thus saving her from having to rent it out week by week for all the time I was there.

Note from Kristin: I recommend trying sites like airbnb.com and vrbo.com because they have a vetting process to ensure safety and security.

4.  Go in the off-season

When it’s not busy, the locals will have more time to talk to you.  The owners of the cafe I went to regularly in my recent trip to Italy (living in a small town) loved when I brought in my Italian language book and they were a great help in learning the language and talking to me about life there.

5. Have a routine

We go abroad to get away from our routines, but to go local, it is helpful to have some routines in order to meet the locals. If you go to the same cafe around the same time each day, you will meet the locals who also go around the same time each day (and you will get to know the owner). Walking to the café in the morning you will see the same shopkeepers opening their stores each day.  Go to the same grocery store and befriend the owner. Visit with the same four old Italian men on the same bench every night.  Even the sameness of the animals, the same cat sleeping on the moped in the alley near my apartment, the dog that walked with his owner every evening.

I had a routine I did every night in Monterosso right before I would go to bed: I would stand on my balcony and listen to the sounds of the town (really loud from the one bar on weekends, very quiet every other night), look up and see how many stars were out and what phase the moon was in, and always took time to look at the Mediterranean Sea. I was living there, saying good-night to my town.

6. Find an Expat

All places seem to have at least one ex-pat who lives there. They can often be your “in” into the local culture.  Ask around, the locals know the other Americans living near by.

7. Go to local events

These are the things tourists would not go to. I went to hear the local choir in the church and saw all the regulars from the town. Not only was it culturally a great way to learn about the people and place I was in, but it helped me make friends, too.  I went to some off beat events:  a fish fry, an independence celebration, a religious march around the town square, an opening of a new café.

Using the above suggestions will help you meet locals and get a deeper understanding of the culture.  I found that once you meet one person they happily introduce you to the others in town.  You are a celebrity and they get celebrity status just knowing you.  And the smaller the town or more remote the area, the more you get treated like an extinct animal, very special.  The older man I traded English for Italian with got this celebrity status because he was my “professore”.  His buddies would punch him when I started walking up, and then loved it when we would do the Italian hello (kisses on each cheek). They all wanted to practice their English and would have me sit with them on the bench (and since this was a small town off-season, it was the evening entertainment for all of us!).

Don’t underestimate this specialness; within a day or two of my arrival, most of the town knew that there was an American woman living on Via Magenta.  It led to meeting more people, like my friend Alisia who came up to me and said “Hi Francesca” as if we were already friends. Or when I was sitting in the square, people saying hi and my name.  And it felt good when I was leaving when townspeople I didn’t even know said things like “Buon viaggio domani”. (Have a good trip tomorrow).

Living local for your career break is an ADVENTURE!  Be prepared to have surprises come up. And be prepared for changes, concrete and tangible as well as personal.

Recommended Resources

Language schools

• In San Francisco: Italingua
• In Italy:  Nel Blu

Local culture/local events

• Rebuild Monterosso
• Save Vernazza

Apartments

• Holiday Apartments Villas Cottages in Cinque Terre
• Tripadvisor
• Rick Steve’s on Italy

 Meet Fran and hear more of how she traveled locally in Italy at Meet Plan Go on October 16.

Fran Wickner, Ph.D., MFT is a therapist near Berkeley, California who helps individuals, couples and families deal with transitions, stress, relationship concerns, separations, parenting, anxiety, addictions and job issues.  She helps people move towards solutions, such as taking career breaks when they are having burn-out at work or helping those who love their jobs and would like to take a break so they can return with a renewed sense of well being and creativity. 

You can reach her at franwickner@hotmail.com, 510-527-4011, www.franwickner.com .

In the midst of Meet Plan Go planning activities for the San Francisco event on October 16, I took a break in the day and stopped by AFAR Media’s offices in downtown San Francisco to host a chat on career breaks with AFAR’s followers on Facebook. Davina Baum, the digital director, welcomed me, and walked me down a hallway where future magazine pages were hung. We passed large, stunning pictures of people and places around the world. The office staff sat at low desks spread over an open space, humming away, at what I presumed was AFAR.com, the magazine, and the upcoming AFAR Experiences trip to South Africa. This office was all travel.

I’ve come to know AFAR Media closely over the past year, first as an attendee in focus groups and then all over the travel circles in San Francisco and online. Recently, I became an AFAR Ambassador, posting highlights, making the very-addicting wanderlists, and answering questions on AFAR.com.

However, this was my first Facebook chat. I was nervous, but ready to cover all sorts of questions that their 12,000+ followers on Facebook could possibly have.  The hour flew by and so I leave the informational remnants for you here.  Below is an abbreviated recap of the chat, meant to capture the essence of the discussion and my answers on career break topics like planning, budgeting, solo travel, living, working, and volunteering abroad.

The world’s a big place. How do you decide where to go?

I think the best way to decide where to go is to ask yourself, “If anything was possible, where have I always wanted to go?”

That’s kind of obvious, so it’s important to pay attention to things we naturally gravitate towards like Parisian style cafes or Korean BBQs, or pictures that spark our interest like the blue Tahitian waters. It’s best to follow that spark and ask yourself why want to go there and dig a little more.

What about money? Obviously, it depends on what kind of trip you want to take, but is there a rule of thumb for how much you should save up?

Practically, I have a budgeting method that I follow once I decide on the places and activities I want to do. For each country you want to visit, look at the lodging costs a place you’d feel comfortable in, then times that by 3. That’s a good estimate of cost per day. Then, times that by the number of days and you should have a good estimate what your time in that country will be. Do that for each country and add it up.

Getting a good budget estimate, I feel, takes the abstract and makes in concrete because you know the amount to save for.

• How To Estimate a Travel Budget: An Introduction
• Before You Go: Budgeting and Saving for Travel

How did you manage to pay all your trips?

The easy answer is that save a lot when I’m ready to go on a big trip. The bigger answer is that when I traveled from 2008 to 2010, I freelanced between trips and then saved. Here is more information on how I worked as a consultant to pay for my big trips.

Other career breakers I’ve met live off of savings or work abroad. It’s surprising, but it may actually be cheaper to live abroad than at home in the US.

I also love this article on why living and working abroad is good in a down economy. The US is recovering right now, but still the reasons hold.

If you had one chance to go anywhere in the world tomorrow, where would you go?

This is a question I am always thinking about: I’d like to do a culinary tour of Mexico, Carnivale in Rio, travel the Silk Road, do a foodie tour of Paris and France with my best friend, and trek in Ethiopia.

If you wanted to take a career break, how far in advance do you suggest people start planning?

I recommend 6 months to 1 year. It’s a big investment and (beautifully) disruptive to live, so taking this time to think about where you want to go, save up, make contacts, and then arrange what you need to works best. If your work has a sabbatical program, that’s even better and you can plan accordingly with your manager.

Do you have any tips about booking flights for long-term travel too? Did you book yours in advance or as you went?

For flights, I recommend 21-90 days out for your big haul flights, but leave the in country travel to more the last minute.  In my experience, I feel that if I have my beginning and end, I’m ok. When I have done short in country or between country flights, I felt trapped by an itinerary once in country because there’s such a beautiful serendipity once you’re on the road that makes “must get to airport on this date” seem overwhelming.

Others may like that though. For example, I was going from Jordan to Turkey in 2009 and really wanted to go to Syria, but couldn’t because I booked a flight so far in advance and had to be in Turkey on a certain date. I even found out that there were no savings with the flight booked in advance, so that I regret that.

Another community member recommended using Airtreks for around the world point-to-point tickets.

What do you absolutely need to bring with you when you’re traveling for a long time?

Life on the road means everything you need must fit into a backpack. For must haves: iPod with This American Life podcasts for long bus and train rides. Then, I bring a good pair of hiking shoes and flip-flops, a headlamp for reading, my Moleskine for notes and contact information. I bring my sarong and swimsuit for impromptu beach happenings, sunscreen (it’s expensive abroad!), natural mosquito repellent and pictures of my family, friends, and places I grew up or live. Clothes can be found anywhere and replaced, but I start out with three pants, five to six tops, and a warm fleece. Here’s my list of what I packed for four months in India, Southeast Asia, and Morocco.

What are your thoughts on the decision between long-term travel through multiple countries and actually living in a foreign city for an extended period?

It all depends on the type of trip you want to take. Do you have a bucket list of activities and places, a finite period of time off, and a plan for when you come home? Then, I recommend getting an around the world ticket and checking those items off your bucket list. Two of my speakers at this year’s event did just that (with a little serendipity mixed in) and had their trip of a lifetime.

Personally, I traveled with intentions: I stuck to a particular region and gave myself enough time to hit on main places and activities I wanted to see and do and then let the rest fill in itself on the road. Sometimes this meant staying in one place for a long period of time and others it meant moving on. My regret was always moving on too soon.

I think it depends on the experience that a traveler wants. My friend Sarah loves wine and Italy, so she spent six months working for an agriturismo in Northern Italy.  She took weekend trips and friends visited, but she “settled down” and soaked in all her tiny lake town had to offer.  My friend Alex promotes the idea of slow travel, which is all about letting the place reveal itself to you.

My preference for a big trip is a mix of both because I feel that connection comes when you are in a place for a while and that tie results an opening in the country and culture one wouldn’t get if they just saw a site, stayed for a couple of days, and moved on.

Have you taken big breaks traveling alone? If yes – did you find it challenging in any way?

I have taken the big trips alone, solo travel is incredible because I get to do everything I wanted to do. Still, it did get lonely on the road, so when I felt that way, I made friends. On the road, especially the backpacker route, I found it very easy to meet people – every one expects you to talk to each other.

For safety, I followed a few rules: I didn’t go out at night alone in the Middle East and India and I dress country-appropriate (no shoulders or knees), and finally, I didn’t smile back at everyone. Worse case, I had to make up a husband in Egypt and shout at a guy on a train in Denmark, but overall I felt safe.

• Why Traveling Solo As a Woman is a Good Thing

I think the biggest hurdle was convincing other people (friends/parents) that we weren’t throwing away our careers/real life. Did you run into that? What did you tell people?

I get a lot of question on “what happens to my career if I travel” The good news is: It’s right there where you left it. Your professional experience, network and connections do not go away when you travel and you are more well-rounded person when you return. Your career is what you make of it so you can shape it any way on the road or when you return.

How did you handle naysayers who disagreed with your plans to travel the world?

To deal with naysayers, I did a couple of things: said some version of “This is what I feel is right for me at this time.” and “I am not afraid of finding a job when I get back.” I also found that people responded with admiration that I was following my dream and focused my energy on conversations with them vs. the downers

Do you have any suggestions for volunteering or working during your travels?

There are a couple of resources I can point you too – it really depends what you want to do:

• International Volunteering Resources, Stories, and Advice
• Working-abroad Travel Stories
• One of my fave articles: Work and play: 10 volunteering holidays

Did you do any volunteering/working during your big trip?

I did volunteer three times when I was in India – teaching street kids in Jaipur, helping mentally disabled women in Kolkata with Mother Theresa Charities, and then doing a clinic ridealong in Bihar with the Root Institute. Here are some posts I did about my volunteering experiences to get a sense of what they were like.

How do you bring the lessons of travel into your daily life at home?

I am much more patient waiting in line after having traveled in India It’s actually true; I developed a lot more patience that I practice at home in small situations and then in bigger things. Also, I have tried to let go of needing to plan everything after realizing that everything on the road fell into place, and everything at home usually.

Overall, I really love this post by Jodi of Legal Nomads from all of her travels: It sums up the lessons and experience of long-term travel and career break nicely.

What would be the one most important thing that your extensive travels have taught you?

I have found that I am very comfortable with ambiguity, I trust myself a lot more, and have learned that people have much, much more in common than their differences.

Long-term travel, the career break – It was the best thing I ever did for myself.

—-

Whew! What a great chat and the hour had flown by. The questions the community asked are very typical of those I hear from most people around long-term travel.

Join me and 10 other career-breakers on October 16^th in San Francisco or another city and learn how they would answer your questions too. A portion of the proceeds benefit the AFAR Foundation, which is all about getting young people out to travel.