When to visit
Sweltering in the summer (in particular Florence), Tuscany shows its best sides in the spring and fall. Fall is a great time to visit the slow food-obsessed region, when the cucina contadina (farm cuisine) comes to life with festivals dedicated to seasonal produce, local game, and foraged truffles. September and October are peak months for harvesting grapes. Some vineyards even let visitors roll up their sleeves and help pick grapes while others offer unique experiences such as horseback riding paired with wine tastings.
In June the Tuscans don medieval colors and compete in Roman-style horse races, Renaissance-era “football” games, and traditional boat races. Siena’s world-famous Palio horse race is held later, in July and August. This is also the best time to swim in the Tyrrhenian Sea and Ligurian Sea (many people are unaware that Tuscany also includes a stunning coastline) and hike in the Apuan Alps.
With fewer crowds in Florence, Pisa, and Siena, winter can also be a good time to visit Tuscany. You can even ski and snowboard in Tuscan-Emilian Apennine National Park. Keep in mind, however, that some hotels and restaurants close during the winter months. Castelfalfi, for example, usually closes in January and doesn’t reopen until March or April.
Getting around
The Trenitalia national rail network connects regions in Italy with Tuscany’s major cities. Expect fast, affordable, and reliable public transportation; though some cities, like Siena, require transfers to slower regional trains. Further afield, smaller villages, natural parks, and tourist destinations can only be reached via buses, which don’t always have convenient schedules. Much of the countryside is best seen on indulgent drives along single-lane roads—which also happen to be perfect for cycling.
Traveler tips
To really learn the lay of the land on a “slow-travel” experience, visitors can discover Tuscany on foot. The Via Francigena is an old pilgrimage route that meanders through Tuscany on its way from Canterbury to Rome. With some advance planning, travelers in decent physical shape can easily tackle the sections—called tappe in Italian—from the medieval hill towns of San Gimignano, Monteriggioni, and Siena in three to four days, enjoying food and wine at local farms along the way.
If you prefer to explore by bike, you’re in luck. Tuscany is a popular place to cycle. The months of May, June, September, and October offer the best weather and less traffic. Whether you want a seaside route, rolling hills through the countryside, or climbs in the Alps, you’ll find them here. Many bike rental companies offer guided tours if you don’t want to have to worry about getting lost or fixing your own flat tire.