How to Plan a Trip to Florence, Tuscany, and Sardinia

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 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
  • 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 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

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. 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 Expediaand Expedia has reviews like Trip Advisor so we could get a sense of the place. 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. Based on my experience with in other cities, I would recommend using them.

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.

Car Rentals in Italy


  • 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 airlinesthat 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?

I’m also taking along my favorite series of guidebook: DK Eyewitness Travel Guide: Italy
. 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!

I Recommend These Italy Tours:

Iconic Italy –>  “Experience two inspirational weeks in Italy, connecting with the some of the greatest cultural highlights in the world. Get in touch with the ancient past alongside an archaeologist among the ash-preserved ruins of Pompeii, marvel at Renaissance treasures in iconic Venice and enchanting Florence, and stop and smell the lemons in the quaint cliff-side villages of the Amalfi Coast. Introduce yourself to the Italian lifestyle and it’ll remain with you always. “Learn More About The Trip>

Local Living in Southern Tuscany –> “Experience life the local way and you’ll experience a Tuscany that most tourists miss. This trip offers plenty of opportunity to get your hands dirty during a cooking class, as youll learn to prepare and enjoy this picturesque regions culinary and viticultural delights. Peruse the local markets and delis in search of the finest organic fare, sample wines in the very vineyards that produced them, and work off all that deliciousness with walks through some of the worlds most beautiful scenery. Just start forwarding your mail here now. “Learn More About This Trip >

Photocredits: Photo by MojoBaron on Flickr

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One Response to “How to Plan a Trip to Florence, Tuscany, and Sardinia”

  1. May 6, 2015 at 2:35 am #

    Nice tips in this article but are 3 days in Sardinia enough to visit the whole region? Thanks.

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