Road trip
Tuscany road trip: a ready-made 7-day itinerary for two
Florence steak and Ponte Vecchio, Chianti wineries and rolling fields, hill villages, two nights near the sea, and the Leaning Tower before your flight home. Seven days, three bases, and you can book every step right here, day by day.
The trip at a glance
- Who it’s for: couples or two friends who love wine, food and country drives
- When: April to June, or September and October. In July Florence is hot and packed, and in September Chianti has the grape harvest
- The route: two nights in Florence, two in Chianti and two near the coast around Bolgheri. On the last day, Pisa and your flight home
- Getting around: on foot in Florence, then a rental car. The longest drive is about an hour
Flights and the car
From the US and Canada, the easiest way is usually a nonstop flight to Rome or Milan, then a fast train to Florence: about 1½ hours from Rome, about 2 from Milan. You can also fly into Florence or Pisa with one connection.
You don’t need a car in Florence, so pick it up on day 3 at Florence airport, a short tram ride from the center, and return it there on the last day. Returning it somewhere else can add a big one-way fee.
Day 1: Florence
Train into central Florence. Spend the evening on Ponte Vecchio after sunset. One of our best wine moments ever was right there, with a street musician playing great music.
Stay: Florence, 2 nights. We usually stay in boutique hotels, which can be fairly priced right in the center if you book early. Smaller guesthouses may not have an elevator, so you might carry your bags up a few floors.
Day 2: Florence, and the steak
Walk from the Duomo past the Uffizi to the river, and have steak in the evening. Florence is a steak town, and it’s excellent here. We recommend Trattoria dall’Oste Chianineria at Via dei Cerchi 40/R. There are several places with the same name in the center, so check the address.
⚽ If you’re there during the season, check Fiorentina’s home games in our soccer calendar.
Day 3: To Chianti
Pick up the car at Florence airport and drive about an hour south into the rolling hills of Chianti. The Tuscan countryside is a joy to drive. Stay at a winery or a farm stay, so you can taste without worrying about driving.
Stay: Chianti, 2 nights, ideally at a winery.
Day 4: The winery
A winery tour with a tasting and a long lunch. On our own winery day near Florence, what made it special was that there was plenty of both wine and food: everyone thought the cheese and cold cuts were lunch, but the food just kept coming. In the afternoon, walk around a small village, such as Greve in Chianti.
Day 5: Peccioli, Lajatico and the coast
West from Chianti into the Valdera hills. In 2024, Peccioli was voted Italy’s most beautiful village in the national Borgo dei Borghi contest, and its lanes are full of modern art. Next door, in Lajatico, Andrea Bocelli’s hometown, is the Teatro del Silenzio, an open-air stage in the middle of the fields. It’s worth a look if you like that kind of music at all, and the concerts are in July. There’s little lodging in the villages, so in the afternoon continue about an hour to the coast around Bolgheri.
Stay: around Bolgheri and Castagneto Carducci, 2 nights, for example at a farm stay near the sea. We haven’t stayed here ourselves, so choose by reviews.
Day 6: The sea, or Bolgheri wines
A beach day at Marina di Castagneto, or the Bolgheri wineries, whose reds are among the most respected in Italy. A famous cypress avenue leads to the little village of Bolgheri. Book a guided winery visit ahead. We haven’t been to Bolgheri ourselves, so this is based on other travelers’ reports.
Day 7: Pisa, and home
About an hour north to Pisa. The Leaning Tower and the cathedral are on the same square, so an hour is plenty. From Pisa to Florence airport is about an hour. Return the car and fly home, or take the tram to the station and the train back to Rome or Milan for your flight.
What it costs
A rough estimate for two in April or September, flying from the East Coast:
- Flights: about $1,300 to $1,800 for two, round trip to Rome or Milan. More from the West Coast
- Rental car: about $225 to $400 for five days
- Stays: about $875 to $1,450 for six nights
- Winery tour: about $110 to $225 for two
- Food: about $100 to $145 a day for two
All in, roughly $3,200 to $4,800 for two. Florence is the most expensive stay on the route. Prices change a lot with the season and how early you book, so treat these as a ballpark.
Cook the region at home with our Tuscan recipes.
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