DESTINATIONS · TUSCANY
Plan Tuscany beyond Florence
Hill towns, Chianti wine country, the Val d’Orcia and the walled cities of Siena, Lucca and Pisa, with Florence as your base or your first stop.
Why choose Tuscany?
Tuscany rewards travelers who pick a base and explore outward. Florence gives you the art and the rail connections. The countryside gives you vineyards, small towns and long lunches. Most first trips combine the two instead of trying to see everything.
Best for: art, wine, food, hill towns, slow road trips and first-time visitors to Italy. Ideal stay: 4–5 days for Florence plus one or two day trips, 7–10 days if you add a countryside base.
Where to go in Tuscany
Florence
The regional capital and the easiest base: Renaissance art, walkable neighborhoods and direct trains to Siena, Pisa and Lucca.
Siena
A medieval city built around one great piazza, about 1 hour 30 minutes from Florence by direct regional train.
San Gimignano
The town of stone towers. It has no train station, so plan a bus connection, a car or a tour.
Chianti
Vineyards and wine estates between Florence and Siena. Wine tastings and driving do not mix, so most visitors book a tour.
Lucca and Pisa
Two easy train trips that pair well in one day: the Leaning Tower in the morning, Lucca’s walls in the afternoon.
Val d’Orcia
Cypress roads, Pienza and Montalcino. It is the part of Tuscany that most needs a car or a tour.
What to do in Tuscany
See Renaissance art
Start in Florence with the Duomo and the David, then look for quieter art towns once you have seen the icons.
Taste the wine country
Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano all come from Tuscany. A guided tasting day lets everyone drink.
Sleep in the countryside
An agriturismo, a working farm that hosts guests, turns Tuscany from a day trip into a slower stay.
Want the full picture of day trips, trains and what each one needs? The Italy2Love guide to the best things to do in Italy puts Tuscany in context with the rest of the country.
Selected Tuscany experiences
Some links in this section lead to experiences Italy2Love has reviewed. If you book through them, Italy2Love earns a commission at no extra cost to you. A commission never changes what we recommend or the order we list it in.
Tuscany day trip: Siena, San Gimignano and Pisa
Three towns in one 12-hour day, rated 4.9/5 on 24,043 Viator reviews, from about €95 (checked September 2026). Best if you want the highlights without managing connections.
Chianti wine tour from Florence
Wineries without the driving, from about €130 (checked September 2026). Minimum age is 18 and groups go up to 27 people.
Chianti e-bike tour
The self-guided version starts from about €45 (checked September 2026) and does not include a guide, winery visit, lunch or wine.
Vespa tour of the Tuscan hills
Ride a Vespa through the hills near Florence. You need your original driver’s license and must be 18 or older.
Florence walking tour with the David
A guided walk with the Duomo and the Accademia, from about €55 (checked September 2026).
Plan your Tuscany trip
How many days?
3–4 days: Florence plus one day trip. 5–7 days: Florence, then a countryside base in Chianti or near Siena. 8–10 days: add the Val d’Orcia or the coast.
Do you need a car?
Not for Florence, Siena, Pisa or Lucca, which all have direct trains. A car helps in Chianti and the Val d’Orcia, but Italy’s drink-driving limit is 0.5 g/l, and zero for drivers in their first three years with a license, according to ACI (Automobile Club d’Italia). If tastings are the point, book a tour.
When to visit?
Spring and fall are the most comfortable seasons for walking the hill towns. Early fall adds the grape harvest, the vendemmia. Summer brings heat and crowds; winter suits Florence’s museums and food more than the countryside.
Frequently asked questions
What is the best base for visiting Tuscany?
Florence is the best base for a first trip without a car, because direct trains reach Siena, Pisa and Lucca. For a slower trip with a car, stay in the countryside between Florence and Siena, in the Chianti area, and use day trips to reach the hill towns.
Can you visit Tuscany without a car?
Yes, if you focus on the cities. Florence, Siena, Pisa and Lucca are all connected by direct regional trains. San Gimignano needs a train plus a local bus, and Chianti and the Val d’Orcia are much easier with a car or a guided tour.
How many days do you need in Tuscany?
Plan at least four or five days for Florence and one or two day trips. With seven to ten days, you can add a countryside base in Chianti or near Siena and include the Val d’Orcia without spending every day in transit.
Is a Chianti wine tour worth it?
It is worth it if tastings are the goal, because the wineries sit on country roads and driving after several tastings is not an option. The Chianti tour Italy2Love reviewed has a minimum age of 18 and groups of up to 27 people, so check both before booking.
What is the best time to visit Tuscany?
Spring and fall are the most comfortable seasons for hill towns and countryside. Early fall is harvest season in the vineyards. Summer is hot and busy, while winter works better for Florence’s museums and restaurants than for the countryside.
Tuscany is more than one city
Use Florence for the art, then give the countryside at least one unhurried day.