4-Day Itinerary // Tuscany, Italy
All I can say about Tuscany is that after visiting, we decided we might live in Italy. At a minimum, we looked at villas to buy to retire in (see here, or here).
Tuscany, a beautiful region in central Italy, has such a romantic aura, with sunsets that cast golden glows over fields of wheat and wine, and cypress trees that line the hills leading up to majestic castles.
We knew we wanted to spend at least 5 days in Tuscany, and we ended up breaking it up into two (in order to go to Osteria Francescana, which was well worth it!): Florence and a short drive through Tuscany, then a 2-night stay at Borgo Santo Pietro.
If you’re headed to Tuscany soon, here is a 4-6 day itinerary for you.
Day 1: Florence
Spend your first day in Florence, the birthplace of the Renaissance. The city is small, but beautiful, and these are some of the architecture, museums and vantage points we recommend:
The Duomo: The Cathedral of Santa Maria del Fiore here in Florence is one of the most stunning architectural gems I have ever seen. No one talks about this cathedral, but the green, pink, and white marble are organized in such a stunning pattern, and the dome can be seen miles away, peaking out above all its neighboring buildings.
Uffizi Gallery: prominent art museum that has gorgeous halls and so much art to explore. It’s worth spending at least half a day here.
Galleria dell’Accademia: best known as the home of Michelangelo’s David. The marble sculpture really is special, and is the focal point of the museum.
Ponte Vecchio: Italian for “old bridge,” this was the only bridge across the Arno in Florence until 1218.
Piazzale Michelangelo: a square on a hill overlooking all of Florence. Go at sunset for some of the best views of Florence. You can take a car/taxi, but we found walking to be very enjoyable and not strenuous. There are also cute cafes here you can eat at.
We also recommend watching Stanley Tucci’s Searching for Italy episode on Florence. We learned so much and were able to appreciate Florence much more because of it. If you have more than 4 days in Tuscany, I would recommend a second day here just to explore more and enjoy the galleries at a more leisurely pace. But it can definitely be done in one day.
Day 2: Siena and San Gimignano
Take a day trip to Siena, a charming medieval town famous for its Palio horse race, and San Gimignano, a UNESCO World Heritage Site known for its well-preserved medieval architecture and towers. In Siena, visit the magnificent Piazza del Campo, the Cathedral of Santa Maria Assunta, and the Torre del Mangia.
In San Gimignano, explore the town’s narrow streets and alleys, visit the Duomo, and climb the Torre Grossa for panoramic views of the surrounding countryside. We loved our sunset dinner at Le Vecchie Mura in San Gimignano, and recommend you stop by Gelateria Dondoli for the best gelato in Italy (they are a many year gelato world champion). The hardest part will be choosing from their myriad flavors.
Day 3: Chianti Wineries
On your third day, explore the beautiful Chianti region, famous for its picturesque landscapes and excellent wine. Along the SS222 road from Florence to Siena, which cuts across the “Chianti Classico,” you can find these five villages that are worth visiting: Greve in Chianti, Panzano in Chianti, Radda in Chianti, Gaiole in Chianti and Castellina in Chianti.
If you’re tired of exploring old towns in the region, visit some of the many wineries in the area and taste the local Chianti Classico wine. We wanted to find a really unique winery, having been to many wineries in Napa/Sonoma and various other wine regions in the world, and Antinori nel Chianti Classico was that winery for us. The architecture of this place was massive, and the long lines of red metal juxtaposed the greenery of the vineyards that sat on top of it.
The staircase that ran up the building from the underground garage to floor level up to the roof spiraled increasingly openly until you were led seemingly into the sky.
We grabbed a late lunch here, and the wine and food were good, but the dessert was incredible. We had Cantucci e Vin Santo, or biscotti with dessert wine, a classic Tuscan dessert that is to die for. Traditionally, people dip the biscotti into the dessert wine, and the wine softens the hard biscotti while infusing it with its flavor—it’s truly heavenly. Things we learned from Tucci’s Florence episode!
Day 4: Pisa and Lucca
Take a day trip to Pisa, home of the iconic Leaning Tower, and the charming town of Lucca.
Start your day in Pisa, visiting the famous Leaning Tower of Pisa, then walk through the Piazza dei Miracoli, the Cathedral, and the Baptistery. The town and area are not huge, so this shouldn’t take much more than a few hours.
After lunch, make your way to Lucca, where you can stroll through the town’s picturesque streets and visit the Cathedral of San Martino, the Piazza Anfiteatro, and the Guinigi Tower. End your day by dining at the famous Buca di Sant’Antonio Restaurant, which serves delicious traditional Tuscan cuisine.
Day 5: Stay in an Ancient Villa
One of the best things to do in Tuscany, if you can, is to stay at an ancient villa. These properties have such incredible history, and their grand estates are beautiful places to just get away and relax for a weekend.
This stay was what M most looked forward to, and it was probably the best of our trip. There are many villas to choose from, and the stays range from a farm stay (where you help take care of the farm) to ultra-luxury, where you can take helicopter tours out to Venice and come back in time for dinner. Here are some of the other villas we considered and would stay at in the future:
We opted for Borgo Santo Pietro, a 12th century castle that was converted into a hotel and farm, and we loved every second of our stay. And if you book with Amextravel.com, you can get upgraded. They upgraded us to a junior suite, which had a fireplace, daybed, and freestanding soaking tub, with views out over their garden and winery. It was absolutely incredible.
We rented bikes and relaxed, met some people, swam in the pool, did a yoga class, toured the farm, got a manicure, and ate at both their restaurants. We would have also loved to watch their cheesemaking demonstration and wine cellar tour — next time.
Breakfast was the best of our trip, with every ingredient locally sourced, many of them on their own farm. The cheeses, cured meats, eggs, and jams that were all seriously phenomenal, and the honey was some of the best I’ve ever had. They also had a full menu of egg-featured breakfast foods, and I dream of those breakfasts to this day.
Day 6: Val d’Orcia
Start your day by taking a hot air balloon ride over the beautiful Tuscan countryside. The scenery will be unreal. Then spend the day exploring the beautiful Val d’Orcia, a UNESCO World Heritage site known for its rolling hills, beautiful villages, and stunning vistas. Visit the famous Montalcino and/or Montepulciano vineyards and taste some of the region’s best wines (if you’re not wine-d out already!), or just drive around. This blog post shares some stunning drives in the region to consider!
We didn’t make it here because we didn’t have time and it was quite a drive to get to, but the valley looks stunning and we’ll be back for it!
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There you have it, a perfect six-day itinerary that will take you through the beautiful cities and towns of Tuscany. Enjoy your trip!
Tips for your trip
As you can tell from this itinerary, exploring Tuscany without a car can get really expensive really fast. But when renting a car here, be prepared to pay some tickets. When we were in Florence, we knew that we had to explore the Tuscan countryside, and decided that renting a car was the best choice for us given our itinerary. Unfortunately, Florence has notoriously awful streets with ZTLs (”Zona Traffico Limitado,” or Limited Traffic Zones, which forbid traffic during certain hours of the day) everywhere. We had read about lots of foreigners getting ticketed left and right, and we joined their ranks. The parking garage we rented from was in a ZTL, and they literally mailed us a ticket that found its way from CA to our updated address in NY. We promptly paid that ticket. All this to say that while it may seem cheap to rent a car, be prepared for some unexpected costs!
For what to eat in the Tuscan region, see my blog post on What to Eat in Italy!
