With its hilltop medieval towns and rolling landscapes, art-filled cities and vineyard-set villas, Tuscany epitomizes Italy for many travelers. After all, this is the birthplace of Italian icons like Leonardo da Vinci and poet Dante Alighieri, considered the father of the Italian language, and of si…gnature flavors like bisteca Fiorentina and Chianti wine. Bordered on the west by the Tyrrhenian Sea, Tuscany’s position in the heart of the Italian boot is particularly apt. There’s a lot of history (including several UNESCO World Heritage Sites) to soak up here, starting from the days of the ancient Etruscans, after whom the region is named, through the era of the powerful Medici clan, makers of Popes and patrons of the Renaissance. Explore cities like Florence, Siena, Pisa, and Lucca, each filled with plenty of cultural, dining, and retail distractions, then spend some time in the countryside, taking in historic towns, legendary wineries, and nearly 250 miles of coastline.
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Tuscany is one of Italy’s top tourist destinations, so it’s never really out of season—but there are times when it’s quieter. Though it can be humid, July and August draw the most tourists, both to cities like Florence and to the coast, as many Italians head to the sea for their August holidays. April to early June, September, and October are idyllic, with the sun shining well into the fall months. Foodies should stop by during the October and November harvest season to take in festivals celebrating things like wine, truffles, and chestnuts. Locals love February: The New Year’s Day crowds have thinned, the weather is crisp, and you might be the only ones exploring the sites.
International flights land in Florence’s Aeroporto di Firenze (FLR), located about 2.5 miles west of the city center, and Pisa International Airport (PSR), also known as Galileo Galilei Airport and set less than a mile from town. No direct flights are available from the United States, but North American travelers can connect through an array of European hubs, including London, Paris, and Amsterdam. Taxis and bus services are available at both airports. Once in town, buses are the easiest way to get around, but note that many of the historic centers are pedestrian-only. Trains are also a dependable option, with regular services available between Florence and major spots like Pisa, Lucca, and Arezzo. The bus is more convenient between Florence and Siena, and to reach hilltop towns like San Gimignano and Volterra. But to really explore Tuscany, renting a car is best; many of the international rental companies, including Hertz, Avis, and Dollar, have offices at the airports and in town, but make sure to request automatic transmissions in advance.
Where to start? In Florence, don’t miss the Uffizi for the paintings, the Accademia for Michelangelo’s David, and fresco-laden churches like Santa Croce and Santa Maria Novella, capped off by a stroll along the Arno and across the Ponte Vecchio bridge. In Pisa, the Leaning Tower (or simply, “The Tower”) is a must for the photo ops, while Siena’s central Piazza del Campo—home to the Gothic Palazzo Pubblico and a 14th-century tower, and surrounded by the brick-faced historic center—is a visitor favorite. Day trips to medieval hill towns like San Gimignano, Volterra, and Montalcino add plenty of charm and authentic flavor—especially in Pienza, famous for cheese, and Montalcino, home of Brunello wine. Don’t leave without a visit to a vineyard and, if the sun’s out, a stroll along the beach at Forte dei Marmi or Viareggio.
All of today’s foodie buzzwords—“local,” “seasonal,” “farm-to-table”—have long been the norm in Tuscany, where the rolling hills are home to farms, vineyards, olive groves, and dairies, and the forests are filled with edible fungi and wild boar. Traditional Tuscan cuisine was born of the idea of cucina povera (poor cooking), which means rustic, unfussy meals made with just a few fresh ingredients (and using olive oil over butter), designed to be shared family-style. Many dishes are based on hearty ingredients like meats and beans, the latter earning Tuscans the nickname mangiafagioli, or “bean eaters.” As with much of Italy, each Tuscan town has its signature products and dishes, from Pistola’s chestnut cake and Pienza’s pecorino to Carmignano’s figs. But general regional signatures include ribolita (a vegetable and bread soup), panzanella (a bread-based salad), grilled vegetables topped with olive oil, and bisteca Fiorentina, the famously thick Florentine T-bone steak. Pasta favorites include tagliatelle al tartufo (a truffle sauce, complemented with fresh truffles in season), and pappardelle with ragu of wild boar (cinghiale) or wild hare (lepre). Top it all off with some cantucci cookies, and wash it down with Tuscan wines from Chianti, Montalcino (Brunello), Montepulciano, or one of the many other local varietals.
Some powerful forces have called Tuscany home, from the days of the ancient Etruscans, who left a significant artistic and cultural legacy, to the era of the House of Medici, a wealthy banking family whose influences were felt in everything from politics and religion to art and architecture. In the 13th century, Florentine poet Dante Alighieri developed what many consider the basis of the modern Italian language, while in the 15th century, the Renaissance ideals that took root in Florence soon spread to the rest of Italy, heralding an era that celebrated artists, craftsmen, and progressive thinking. Meanwhile, a multi-century rivalry between the regions of Florence and Siena resulted in ode-inspiring epic battles and patriotic traditions that are still honored today. With all this in its history, it’s no surprise that Tuscany is a hotbed of museums, cultural attractions, traditional festivals, and historic sites. Every town has something of note, whether an ancient fresco discovered on a palazzo floor, a monument to a native saint, a world-renowned tilted tower, or a work by a famous artist hanging casually in a church. Florence is the main cultural hub, where you can spend days wandering through museums, palazzos, and gardens, while Siena delivers with a roster of notable art and religious sites, and the thrilling, biannual Palio horse racing festival. The smaller towns are worth a visit for their medieval charm and religious and harvest festivals, the latter offering a great look at Tuscan traditions.
Family is at the soul of Italian culture, and kids are welcomed, accommodated, and cooed over pretty much everywhere you go. In Tuscany, there’s plenty to attract and distract them, too, from beach fun along the coast to exploring castles, dungeons, and tombs in medieval hill towns like Monteriggioni. Several towns, including Siena, Volterra, and San Gimignano, have a Museum of Medieval Torture that will fascinate kids of all ages (as long as they aren’t prone to nightmares), while the town of Collodi honors native “son” Pinocchio with a statue-filled children’s park. Bike rides are another great family activity, particularly in Lucca, where you can ride on wide, relatively flat paths along the ancient city walls. Of course, Florence is a treasure trove of fun, where you can taste your way through the food markets and gelato shops, take kid-focused museum tours, and try your hand at a painting or ceramics class. With its wealth of rentable villas and private homes, Tuscany has also become a favorite for multi-generational getaways and family reunions, offering something for every age to enjoy.
When it comes to wine and olive oil, a bigger price tag doesn’t necessarily mean better: with so much of both produced in Tuscany, you’ll often find that the house wine—served straight-up in a jug or unlabeled bottle—is more than good. If you’re visiting in November or soon after, ask for the “new” olive oil in restaurants, to enjoy the latest post-harvest releases. Skip eating in the main piazzas, which are generally lined with overpriced tourist traps. And if you’re in one of the smaller towns before dinner, join locals for la passiagata, or the evening stroll, when everyone is out to see and be seen.
New York City–based writer and editor Sandra Ramani has been covering travel, wellness, and lifestyle topics for over 15 years. In addition to AFAR and Afar.com, her work has appeared in such publications as Travel + Leisure, Departures, Robb Report, Premier Traveler, Bridal Guide, Organic Spa, NYMag.com, Fodors, Bloomberg Businessweek, and WORTH, among others. She is the author of Day Trips from Dallas & Fort Worth (Globe Pequot Press), and has lived in England, France, and Italy.