Florence is small. Two days will cover the Uffizi, the Duomo and a long walk through Oltrarno. After that, the smartest thing you can do is leave the city. Tuscany surrounds Florence in every direction, and four of its best destinations are less than 90 minutes away. Here is how to fit Siena, San Gimignano, Chianti and Pisa into four memorable day trips.
Day 1: Siena (and Why the Palio Matters)
The most rewarding single day trip from Florence. Siena is a medieval city in stone, built around the shell-shaped Piazza del Campo where the famous Palio horse race runs twice a year. The Duomo, with its black-and-white striped marble, is one of the most striking cathedrals in Italy.
Even outside the Palio season (July 2 and August 16), the city’s neighborhoods (contrade) keep their flags up, their songs alive and their internal rivalries running. Walking through different contrade in a single afternoon, you cross from one tribe to another without leaving the city walls.
How to get there: 90 minutes by car, 90 minutes by direct bus. Trains involve a transfer and are slower.
Day 2: San Gimignano (and Volterra)
San Gimignano is the medieval skyline of the Italian postcard: 14 tall stone towers standing inside a tiny walled town, originally built by rival families as displays of power and refuge against attacks. It takes 90 minutes to see, which is exactly why you should pair it with Volterra.
Volterra, half an hour further west, sits on an Etruscan hilltop with a Roman theater, a medieval alabaster industry and views that stretch to the sea. The combination of San Gimignano in the morning and Volterra in the afternoon is one of the great Tuscan day-trip routes.
How to get there: car only. There is no efficient public transport combining both.
Day 3: The Chianti Wine Route
Between Florence and Siena, the Chianti hills are dotted with vineyards, olive groves, hilltop villages and family-run wineries open to visits and tastings. The classic route goes through Greve in Chianti, Panzano, Radda and Castellina, with stops at producers along the way.
Most wineries require an appointment for tastings, but small ones often welcome walk-ins. A typical tasting costs 15 to 30 euros and includes three or four wines, sometimes with bread, oil and salumi. Aim for two wineries in a day, not five: you want to taste, not survive.
How to get there: car or organized tour. The Strada Chiantigiana (SR222) is one of the most beautiful drives in Tuscany.
Day 4: Pisa (and Lucca)
Pisa deserves an honest assessment: the Leaning Tower is impressive for ten minutes, the Cathedral and the Baptistry next to it for another hour. After that, Pisa has limited appeal. Smart travelers combine it with Lucca, only 30 minutes away.
Lucca is a small Renaissance city completely surrounded by intact 16th-century walls. The walls are wide enough to walk or cycle on, looping around the entire old town. Inside, the streets are pedestrian, the cafes are family-run and the pace is slower than anywhere else in Tuscany. Two hours in Pisa, four hours in Lucca, dinner back in Florence: a perfect last day.
How to get there: direct train Florence-Pisa (1 hour), then local train Pisa-Lucca (30 minutes).
How to Get Around: Train vs Car vs Tour
For Siena and Pisa, the train is fine. For San Gimignano, Volterra and Chianti, you need a car or an organized tour. Renting a small car in Florence costs around 40 to 60 euros a day plus parking. If you do not want to drive on Tuscan country roads with locals overtaking you on blind curves, the smart move is to book a tour for the Chianti and San Gimignano days and use trains for the rest.
