Florence & Tuscany - Italy
Overview: A short trip through Tuscany with a stop in Florence
Duration: 3 to 4 days, including travel
Locations visited: Florence, Tuscany, and Montepulciano
How to get there: Fly into either Rome’s Leonardo da Vinci International Airport (FCO) and drive 2–4 hours, or fly into Florence’s Amerigo Vespucci Airport (FLR).
How to get around: Rental Car or Taxi. Major cities can be reached by train.
When to go: Summer is classic, but the weather is decent year-round. We visited around New Year’s.
Pace: Slow to Moderate
Future trips: Explore more of Tuscany, including San Gimignano, Pisa, Sienna, Monteriggioni, and Volterra
View of Florence from the Piazzale Michelangelo
Day 1: Drive from Rome
We picked up our rental car in Rome and started the 3–4 hour drive (depending on traffic) to our accommodations near San Giustino Valdarno in Tuscany, about an hour south of Florence. The drive through the Tuscan countryside is picturesque.
With a slightly delayed start, a few issues at the car rental pick-up, traffic, a lunch stop, and some general exhaustion from our time in Rome, we kept it easy once we arrived. We explored the resort a bit and enjoyed dinner at one of its restaurants.
Day 2: Florence
We started the day early, driving about an hour to Florence. While Florence is the largest city in the region, you can cover most of its highlights in a day.
Florence is renowned for its leather goods and walk-up wine bars, where you can order wine through a window and take it to go.
After grabbing coffee and a bite at a café, we headed to Florence’s most notable landmark: the Cathedral of Santa Maria del Fiore (commonly called the Duomo). The exterior features green, pink, and white marble, creating its iconic design alongside the massive dome. Next to the cathedral is the Baptistery of St. John.
We waited about 30 minutes to enter the cathedral. You can also opt to climb the dome (either instead of or in addition to seeing the cathedral interior).
Other notable churches to see in Florence include the Basilica of Santa Maria Novella, Basilica of Santa Croce, the Basilica of San Lorenzo, and the Basilica di San Miniato.
After exploring the cathedral, we visited nearby squares, including Piazza della Repubblica and Piazza della Signoria. The latter features landmarks such as Palazzo Vecchio, the Fountain of Neptune, and Loggia dei Lanzi. Later that evening, we caught an exciting performance with climbers on the Palazzo Vecchio.
While we didn’t have time, the Uffizi Galleries (home to Renaissance masterpieces) are also located near Piazza della Signoria.
Florence’s famous bridges are within walking distance:
Ponte Vecchio (lined with jewelry and souvenir shops)
Ponte Santa Trinita
Ponte alla Carraia
Across the river lies the Basilica di Santo Spirito and the Boboli Gardens, which are highly recommended (though we didn’t make it). Nearby, you’ll find the Forte di Belvedere and Palazzo Pitti art museum.
For breathtaking views, head to Piazzale Michelangelo, where you can see the Duomo, Palazzo Vecchio, and Basilica of Santa Croce. Nearby is the Basilica di San Miniato, and on the way up or down, don’t miss Porta San Niccolò, a 14th-century fortification gate.
Finally, Florence is home to Michelangelo's David, housed in the Galleria dell'Accademia. Despite visiting during the busy New Year’s season, I managed to secure a timed ticket on the day of.
This concludes the sightseeing portion of our trip to Florence. We were in the city for New Year’s Eve, and then headed to dinner and drinks.
Day 3: Wineries
On New Year’s Day, we visited a small family-owned winery, Azienda Agricola Podere San Pierino, in the heart of Chianti. The region is famous for Chianti Classico, a bold red wine made from at least 80% Sangiovese grapes.
Italy uses the largest number of grape varietals globally—over 350 approved varieties—compared to just 20 for most French wines. This diversity gives each region its unique wine characteristics.
Be sure to grab some wine, olive oil, or food from the wineries. Many offer international shipping. For us, shipping a case of wine to the U.S. cost only about $20 per bottle.
If you have more time, explore another winery or one of Tuscany’s villages. Food & Wine has a great list of recommendations.
Day 4: Montepulciano and Drive Back to Rome
On our final day, we explored the resort and its neighboring village before heading back to Rome.
En route, we stopped at Montepulciano, a medieval hilltop town famed for its wine. Parking is limited in town, but there are lots further down the hill with paths leading up.
You can enter the town through one of the small gates - we used the one on the south end of town. From the entrance, there’s many old style streets and buildings that make you feel like you’re in another century. Along the streets you’ll find many cute stores, including coffee shops, wine shops, restaurants, and boutique stores.
At Piazza Grande, Montepulciano’s main square, you’ll find:
Comune di Montepulciano (the town’s iconic building)
Cattedrale di Santa Maria Assunta
Palazzo Nobili-Tarugi
Pozzo dei Grifi e dei Leoni
If time permits, climb the clock tower on the Comune di Montepulciano.
As Montepulciano is a hilltop town, there’s tons of great viewpoints of Tuscany. Val d Orcia da Montepulciano is a popular one. If you have time (we did not), there’s tons of opportunities for wine tasting in the town, including multiple underground cellars.
On the way out of town, you can stop by the Tempio di San Biagio (unfortunately, also something we did not have time for).
After Montepulciano, we drove back to Rome, wrapping up a memorable trip through Tuscany and Florence.
