Planning Your Trip to Tuscany
The more days, the better—but any amount of time in Tuscany is a treat, especially if you plan ahead. If you have a single weekend to spend in the region, focus on Florence and the surrounding area of Chianti, famous for its production of wine and olive oil. With a few more days, consider adding on side trips to medieval San Gimignano and the UNESCO-honored historic center of Siena—and if you have a car, road-trip around Pienza and Montepulciano. With a week or more, go on a bike tour, or head to the coast to relax on beautiful beaches, swim in the Tyrrhenian Sea, and explore quiet coves.
Tuscany in 2 Days
Most travelers prefer to take their time in Tuscany. But if you're visiting the area on part of a larger itinerary through Italy and you have just a couple of days to spend in Tuscany, keep things simple by spending a day in Florence and the next day touring the Chianti wine region, like in this 8-day itinerary.
In Florence, there's so much to see and do: tour the famed Duomo cathedral, see Michelangelo's 'David' sculpture at the Galleria dell'Accademia, have a leisurely lunch or an Aperol spritz at an outdoor café, visit the Uffizi Gallery to view masterpieces by Leonardo da Vinci, Michelangelo, and Caravaggio, catch the sunset from Pontevecchio Bridge, and after dark, go for dinner and drinks in the stylish Sant'Ambrogio neighborhood.
On day two, day-trip into the Chianti wine region, stopping for tours and tastings at wineries like Antinori and Badia a Coltibuono. Enjoy views of the vineyards while tasting locally grown olives and sipping varietals like Chianti Rufina and Chianti Colli Fiorentini. Stop at castles and churches along the way, and if you have time, visit an outdoor marketplace in Greve or Poggibonsi to pick up local produce and charcuterie: you'll have all the fixings for a great picnic the next day. Find out more about what to eat and drink in Tuscany here.
Tuscany in 3-5 Days
With a few more days to spare, add a few more Tuscan destinations to your itinerary. The historic center of Siena is a UNESCO World Heritage Site that's famous for its Gothic cathedral, and San Gimignano is known for its Middle Age-era towers. Both are easy day trips from Florence – and if you're driving, you can stop along the way to visit hilltop towns, wineries, churches, and castles.
For a more structured road trip, try the scenic road between Pienza and Montepulciano through the beautiful region of Val D’Orcia. Along the way, you'll have the option to visit the public garden of Horti Leonini in the village of San Quirico d’Orcia and stop for a traditional Tuscan meal in a local favorite like Il Loggiato, located off the piazza in the village of Bagno Vignoni.
In search of a specific plan? Try this five-day tour, basing yourself in Florence and day-tripping to Tuscan highlights like Siena, Pisa (world-famous for its Leaning Tower) and Lucca, with its charming old city surrounded by well-preserved Renaissance walls.
Find out more about Siena here.
Tuscany in 5-7 Days
If you have five to seven days in Tuscany, you have several options to choose from. You could spend time in Florence at a more relaxed pace, then move onto Chianti for a day or two in wine country. Spend a day sightseeing in Siena or San Gimignano, then explore the twin medieval towns of Montepulciano and Pienza with a local guide.
Finish the trip with two full days in Lucca — plenty of time to walk around the city on a three-hour guided tour, visiting the 11th-century Diavolo Bridge (also known as Ponte della Maddalena), the striking Duomo di San Martino, and the Byzantine-medieval Church of San Frediano. On the last full day, you'll take a pasta-making class. You'll do all of this and more on this classic weeklong itinerary.
Alternatively, devote your time to a special-interest tour focused on wine or architecture, detour to the coast to swim in the Tyrrhenian Sea, or set out on an active itinerary. During this six-day bicycle tour, you'll pedal past vineyards and villages by day and relax in lesser-visited Tuscan destinations like San Miniato and the spa town of Montecatini at night.
Looking for more options for biking around Italy? Check out these itineraries.
Tuscany in 10 Days or More
With ten or more days in Tuscany, you have time to visit Florence and Siena, medieval villages, wine country, and the beach. Many shorter-term visitors — those who have just three or five days — don't make it to the Tuscan coast. But the beaches of the Maremma region, on the coast of the Tyrrhenian Sea in southwest Tuscany, are wonderful to explore. The coast is dotted with quiet coves, pine forests, and wide stretches of white sand.
Further north, near Livorno, the clifftop castle known as Castello del Boccale makes for an incredible photo op at sunset. Other highlights on Tuscany's shoreline include the resort of Castiglione della Pescaia, which faces the islands of Elba and Giglio, the beautiful seaside town of Portoferraio, and the quaint fishing village of Porto Azzurro. Needless to say, it's not hard to find a good seafood dinner in this part of the country.
For an overview of the whole region, try this ten-day itinerary, which begins in Florence, then takes you to Pisa, Siena, Montepulciano, Pienza, and Lucca, where you'll take a pasta-making class. With a few more days, consider this similar two-week itinerary takes you to Montepulciano, Pienza, Siena, and Pisa and includes truffle-hunting in the forest and a winery tour at Brunello di Montalcino, plus a detour to the Cinque Terre in Liguria for a day of hiking.
Read this article for more on how to get off the beaten path in Tuscany.