How to Plan a Big Trip: A Step By Step Guide To Living Your Travel Dreams

When I left one life to travel the world on my first big trip to India in 2008, I had the Lonely Planet guide for India and a picture book called India Unveiled. I was a seasoned traveler in the US, Europe, and Asia for 10 to 14 day vacations, but never on a big trip of this magnitude – I was taking an ultimate leap of faith and turning my back on a career and one life to live my travel dreams. Somehow my Google searches of “How do I move forward into what feels like an abyss to do something I’ve always wanted to do?” were not returning answers on the exact steps I needed to take. Instead, I followed my gut and wisdom (and may have used the occasional spreadsheet) to figure it out. It would have been much easier had I a set of instructions.

When I speak at events like Travel Massive, Meet Plan Go, and the Asia Society, I often get the question of “How did you do it [travel the world]?” I provide this blog to answer that question in small posts, but realized after 3 1/2 years of writing this blog and talking with many, many would-be and returned travelers that I have enough information to write a set of steps for you – the “how to” list that I needed.  I hope you find this helpful and please comment for any other resources that I don’t mention. However, remember, it’s just a guide, you know your situation the best.

1. Own your “Travel the World” desires

Own Your Travel the World Desires

Photo on Flickr by PhillieCasablanca

There’s voice inside of you that may be saying, “I’m miserable, I should just chuck it all and travel the world.” You have some wanderlust and things aren’t working out in daily, stationary life.  And that’s OK – that voice needs to be listened too. However, before yelling “I Quit!” at the top of your lungs into your bosses face and hopping on the next flight on a frustrated impulse,  burning bridges with each step, take the time to think about why you want to travel the world.  Is it to start over, the find your passion, to have some adventure, search for your roots, to escape, or to see the Great Pyramids of Giza? All are valid reasons and can be fulfilled by quitting your job to travel the world. It’s just a matter of respecting all you’ve built with your life thus far and proceeding with grace, not force or frustration.

Own all the reasons you want to travel the world, make them your fuel to begin dreaming, and start to plan your big trip in a smart and methodical way with the faith that this is your next step in life.  You’ll keep in tact and honor your current life- your community, your professional experience, and your home while planning your dream trip to start on the path of a new one – the traveler.

2. Determine where you want to go and set your travel intentions

Determine where you want to go

Photo on Flickr by laadla

You know you have a place in mind, or several. In speaking with many travelers planning their big trips, I have found that there’s a few places they have held deep in their hearts for many years. It’s important to take the vagueries and set some points on a map because you can’t search for plane tickets to “I don’t know” or “I don’t care.” For my first trip, India came to me in a flash of inspiration, even though I knew that I always wanted to travel the world.  It wasn’t until I got a specific country that I could actually start to make the plans. I’ve talked with travelers and they often look at where their airline miles can get them – that’s a great start. They’ve also looked at where your friends lived around the world and thought, “I’ll start from there.” If you need a little help dreaming and like a fun activity, I recommend reading this post on how to determine where to go using visioning techniques to answer the question, “Where do I want to go?”

Once you have a country or two or thirty in mind, think about why you want to go there and what you want to do. This is not creating the itinerary just yet, it’s just listing out all that you want to experience. This phase is important to think about what are the “Must dos” of the big trip. A big trip is a large investment so a traveler needs these guideposts to make sure the trip fulfills its overall purpose. Don’t worry, you won’t be able to plan too much. Serendipity and a lot of the transformation comes from the the journeys to these “must do” experiences and places. The plan you’re putting into place now is just a framework, the magic of travel comes from the in between.

I’ve met travelers who want to volunteer abroad or work abroadlive as a local in a country they love, and or jet around the world. They crafted their trip around their overall intentions and many of the most memorable experiences happened along the way. In my own experience, on my second big trip, I knew that I just wanted to “see the pyramids” and a big trip of two months traveling around Egypt, Jordan, and Turkey in 2009 was born.

4. Start a loose an itinerary

Set travel intentions

Photo on Flickr by iamroco

This is the step when the trip goes from idea to plan. A loose itinerary is the bones of a big trip with timing and logic applied. You’ll use this itinerary to determine a budget and a route, which will lead to savings goals and plane ticket purchasing and, ultimately, departure! To start, access a map and a spreadsheet. On the spreadsheet, label three columns: Country, City, and Estimated Days. Start to list all the places you want to visit  and activities you want to make sure to do in each.  Make guestimates on number of days in each place. Refer to the map and move around destinations that are geographically close by.  If one of intentions is “Spend a month in Paris” No problem, just put Paris and 30 days on the spreadsheet. Add lines between destinations for 1-2 days of travel between each day. Total the estimated days and you have an idea of how long your trip will take.

5. Determine how much this big trip will cost

If you want a quick ball park, take the number of months for your trip and multiply by the following amounts for a frugal budget assuming eating at local restaurants, staying in local accommodations like bed and breakfasts/pensions, budget hotels, hostels, or apartments, and traveling overland by bus, train, and regional budget airline where possible.

Per month:

  • Asia (excluding Japan): $1500
  • Europe (excluding Scandinavia): $2500
  • Africa: $2500
  • Middle East: $2000
  • Central America: $1500
  • South America $2000
  • Japan or Scandinavia $4500
  • Australia or New Zealand: $3500
  • North America: $3000

That’s your first look at a budget for your big trip. It’s a rough estimate, but you can breath easy because you’ve just conquered the myth that taking a big trip is expensive. It’s not – look at your itinerary and how much you can do, how many dreams you can fulfill for under $20,000. Remember that travel is an investment that will pay off for the rest of your life. I also recommend thinking about how much it costs you to live in your current city and how these numbers compare. That ballpark figure is just a high-level estimate, I recommend going through the activities in this budgeting post to determine the more specific costs for your destinations and activities.

1. How to Estimate a Big Trip Budget: Introduction

2. How to Estimate Costs Per Day (Cheaper than you think!)

3. How to Estimate Transportation Costs (It’s not just what Kayak shows you)

4. How to Estimate The Before and After Costs (I.e. what you want to come home to)

6. Look at your current financial situation

You now know your budget and your big trip is going to cost,  now it’s time to look how you can pay for the trip. Take a look at what’s in the old bank account and any debts. From my experience with mid-career professionals and big trip discussions, here’s a typical situation I’ve heard: You have a bunch in savings, you have some student loan debt, maybe a mortgage on a condo, and a nicely funded 401K. The 401K should never be touched, it’s for retirement, not for a big trip. A big trip needs to be funded from money you have, not from money you don’t, so no credit card financing. If you have the money in savings that already covers your big trip budget, then you are in a place to take your big trip whenever you want. If you don’t and or your student loan debt payments are more than 30% of your monthly big trip budget, then you need to save and pay down student loans. I’m not a mortgage expert, but if you don’t have a renter to cover it while you’re gone, then you’ll have to build in that cost to the big trip budget and save for it.

Do this formula:

Money you have available for big trip – Big Trip Budget = Money you need to save for your Big Trip. 

Write that number anywhere and everywhere. It will help you say no to the purchases that do not move you in the direction of your big trip.

I’ve had big trippers ask – “what about working abroad?” And here’s what I say to that, it’s your big trip. You’re quitting your job to travel the world, not fall into another job. If, eventually you want to work abroad, awesome, there are many resources for that. But if you are only saying “I want to work abroad,” because you’re afraid of running out of money and paying for travel, then I recommend that you save and earn here, in America, where you can make a lot more money in your chosen field. Then, go off to see the world without the stress of finding employment in a foreign country. And here’s a secret – once you get on the road, you will meet other travelers who are working and they will tell you how to do it – much more than any Google search and epic plan could.

7. Look at your current life situation

This is is a big step. It’s time to conduct an honest evaluation of the major aspects of your life that will be impacted by your big trip. These usually include, but are not limited to, your job, your home, your family and friends, and your pets. I recommend thinking about what you want to keep in your life AFTER you return from your big trip and do what needs to be done to maintain those ties. All else can be let go.

The good news is that something is prompting you to want a big trip and that something, which is probably coming straight from your heart, will drive your commitment to address all of those areas. There are several big questions to consider:

  • Do you want to come back to your apartment/house? If yes, then start to research subletting options for your apartment and rental opportunities for your home. If not, then start to research how to sell all your things or put them in storage. Remember, if you have friends and family, they most likely will let you crash upon your return, so don’t worry about that. If not, then budget in some hotels and short-term rental options.
  • Do you want to come back to your job? It’s important to remember that no matter the answer,  your network and portfolio are the most important things to preserve pre-big trip so you will have opportunities upon return.  Those must be kept in tact if you want to return to some sort of employment. I have gotten all my jobs by referrals. Start/continue to network with key people at your company. They will remember your good work and will cheer you on once you announce your trip. Review your major projects from the past three years and document the accomplishments in SAR format: Situation, actions, and results. By doing this when all information is fresh and available, you will be able to return with all the facts in place and strong resume. If you do decide to quit, do so with grace. If you want to stay with your job, just not your current position,  talk to your boss about a leave of absence. If you are valued employee in a professional role or your trip is not longer than 3 months, your request should be taken seriously.
  • Do you want to come back to your friends and family (geographically at least)? Consider the most important relationships in your life and decide, can you leave them? If they are not there when you return, then you may want to decide if they are worth sticking around for. Solid relationships will still remain once you return from your trip.
  • Do you have people to take care of your pets while you’re gone? Then bring them back one heckuva souvenir.
  • Do you want to change everything? i.e. do what I did and leave one life behind to start another. If yes, do all of the above. And get rid of most of your stuff. You will never want to come back to boxes of  a George Foreman grill and Gladware after a big trip.

Always, always remember – Your network and your portfolio of experience are of your most valuable career tools. Build them up now like a bank account, they will be there when you return. Your career does not go into a black hole if you leave your job to travel. Your career is your own.

7.  Find your travel community

Meet Plan Go - San Francisco

Naysayers are inevitable, so it’s important find your support system for this big trip. You want to be with people who say, “THAT’S AWESOME!” and not, “That’s irresponsible/what will you do with your job?/when will you grow up?” (The latter statements have all been heard by this big tripper.) In the Bay Area, we are lucky to have groups like Travel Massive, San Francisco World Travelers, Weekday Wanderlust, and Meet Plan Go. In San Francisco, these groups meet once a month or quarter and it’s a friendly place to meet fellow big trippers who will never question your sanity and travel plans. In fact, their response to your questions of “how do I?” and “have you ever been,” will most likely be enthusiastic and helpful. These groups have branches throughout the US, but if you can’t find an in-person support system, start to read travel blogs from big trippers like SoMany Places, LegalNomads, SeatofMySkirt, NomadicMatt, and NeverendingVoyage.

8. Buy the tickets

So you got your spreadsheet, you’ve figured out how far your miles will get you, you’re saving money, you’ve got a stack of Lonely Planets and an Evernote tag for every destination on your itinerary. Congratulations. Now it’s time for the first big, expensive action: buying the plane ticket – the veritable “money where your mouth is” part of the plan. There are a lot of options – an “around the world” ticket, a one way ticket and a prayer, and an itinerary with a set return. No matter what you decide, just buy it. Take this very important and necessary step and all else will fall into place.  Really. Because no matter what, after that purchase, you got your ticket to ride.

9. Start to do all the practical stuff

There’s a whole web site by Meet Plan Go of all the practical steps to take before a big trip, so I’ll leave you to that link for all the big things you need to do: get rid of or store your stuff, manage your apartment and home, talk to your boss, network at your job and share the news- no matter if you are quitting or not – research and get insurance, collect all the items on that packing list, and set up your blog. Take a methodical approach and make a list. Avoid getting overwhelmed by spacing things out in monthly increments. Don’t neglect your relationships and rest assured, the last few weeks will be crazy and frenetic with going away parties and good-byes and then, you’ll be off! And don’t forget to set up your blog – that’s how your friends and family will keep track of you (and that’s how TakeYourBigTrip started).

10. Get excited and stay positive

Get Excited to Travel!

Photo on Flickr by myettethrift 

You’re going to travel around the world!! Keep reminding yourself of this when you have those dark worries about what happens after the trip (magical things!) and if you think you’ll blow through all your money (you will!) come through your mind. Think of it this way –  in five years, you can look back and say, “I traveled the world” and not “I stayed in a job I didn’t like.” Every returned traveler I’ve talked was thankful they took off and traveled. No one said, “I’m glad I stayed where I was.” You’ll be fine, just move forward with your plan, day by day.

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