The First Timer’s Guide to Tuscany
Tuscany is a place that exists as much in the imagination as in real life. Even if you haven’t yet visited the region, which sits just 175 miles north of Rome, you’re almost certainly familiar with its screen-saver-worthy locales, which include Renaissance cities, medieval towns and rolling hills dotted with vineyards. And that’s to say nothing of its rugged coastline, where elegant but easygoing beach hotels routinely draw the coolest people on your Instagram feed.
So, when you’re planning a trip to the area, choosing which of these idyllic sites to see can feel like an impossible task. Do you hunker down in Florence and weave through gallery upon gallery of masterworks, or do you head straight for the hills for a full-on vineyard crawl? Turns out, you don’t have to choose. Within a week or two, you can hit all the highlights.
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Florence
Best for: Getting yourself situated—then getting your culture fix.
The former cradle of the Renaissance, Florence remains jam-packed with the artistic and architectural achievements of some of the Western canon’s biggest names: Michelangelo, Brunelleschi, da Vinci. The city is home to so much beauty, in fact, it gave rise to a phenomenon known as Stendhal syndrome, so named for the 19th-century French writer who described feeling overwhelmed by its aesthetic riches.
You won’t be able to see it all on your trip, but you can hit the high notes in two or three days—especially with the help of a few smart tour bookings. A generalist tour can bring you through the compact city center to admire Santa Maria del Fiore, the monumental green-and-white marble cathedral better known as the Duomo; Piazza della Signoria, the huge square that’s home to the Palazzo Vecchio; and Piazza della Repubblica, with its monumental arch and carousel. If you’re an art aficionado, look for a tour that stops at the Uffizi Galleries (home to Botticelli’s “The Birth of Venus” and paintings by da Vinci, Michelangelo, Raphael and Caravaggio, among others) and the Accademia Gallery, where lines happily form for Michelangelo’s monumental “David” statue.
Hungry yet? Maybe you’ve heard talk of All’Antico Vinaio, the city’s best-known sandwich shop—but skip the long lines and head to Retrobottega instead. Served on schiacciata, a classic Tuscan flatbread, the shop’s artisan sandwiches are top-notch. (We like the Bambola, a winning combination of mortadella, chopped pistachios, ricotta mousse and lime zest.) For a quintessential, no-frills Tuscan trattoria experience, grab a stool at Alla Vecchia Bettola, where diners sit elbow-to-elbow to chow down on fresh house-made pasta and bistecca alla fiorentina, a satisfying but simply cooked regional steak specialty. Or roll up your sleeves and book a Tuscan cooking class in the home of a local—that way, you can bring a little of your trip home with you.
Villa San Michele, A Belmond Hotel, Florence
Where to Stay in Florence
Florence has hotels for every taste and budget. Looking for that elusive combination of convenience and quiet? You can’t beat Hotel Savoy, a Rocco Forte Hotel, where you can bed down in a suite with views of Piazza della Repubblica or the Duomo and nosh on the city’s best club sandwich. If you have an eye for style, chances are you’ll love Hotel Lungarno, owned by the Ferragamo family; hovering right over the Arno River, its polished suites feel like elegant staterooms on a royal yacht. Or you can get out of town altogether and check in to Villa San Michele, A Belmond Hotel, Florence, a Renaissance-era estate set amid terraced gardens just 20 minutes north of the city center by car.
Val D’Orcia
Best for: Uncorking and unwinding.
As Italian wine regions go, Chianti may be more famous than Val d’Orcia, its cousin to the south. But among insiders, it’s the latter that reigns supreme. There, you’ll find all of the same draws—postcard-perfect hillsides studded with olive groves and vineyards, and quaint agriturismi where you can laze the days away sipping wine and learning about farm life—minus the tour-bus crowds.
The valley has five main towns: Montalcino, where Brunello di Montalcino is produced; Pienza, the ideal Renaissance city; Castiglione d’Orcia, a small hill town once ruled by the noble Aldobrandeschi family; Radicofani, which is home to a medieval fortress; and San Quirico d’Orcia, which lies along the Via Francigena, the pilgrimage route from Canterbury to Rome. Between these towns lie tiny hamlets and vast stretches of countryside that invite you to slow down and admire the landscape—you’ll have to, whether you want to or not, since the winding country roads impose natural speed limits.
Sign up for a tour and tasting at a winery to sample this region’s prized red wine. If you want a break from driving, an e-bike riding tour is also a great way to explore the countryside. After working up an appetite, take a cooking class like the one at Podere Il Casale, an agriturismo that produces the cheese and charcuterie served at its restaurant. And make sure to budget time for a visit to Pienza, a UNESCO World Heritage Site built as the ideal Renaissance city, where you can see the hanging gardens at the Palazzo Piccolomini, buy beautiful foulards and enamel jewelry at Officine904 and try local specialties at the casual La Buca delle Fate.
Albergo Posta Marcucci
Where to Stay in the Val d’Orcia
Overnighting at Borgo San Vincenzo, an 18th-century Tuscan villa in the countryside surrounding Montepulciano, will give you a taste of the simple life—albeit a version outfitted with every modern convenience. Albergo Posta Marcucci is an intimate hotel with a series of mineral-rich thermal pools run by the family behind the luxurious Hotel La Perla, Corvara in the Dolomites. And for a truly plush Tuscan getaway, it’s hard to beat Castello di Velona Resort, Thermal Spa & Winery, a luxury hotel in a castle dating back to the 11th century with panoramic views of the Val d’Orcia.
Maremma
Hotel Il Pellicano
Best for: Finding sun, sand and sea—and the places to see and be seen.
After a few days inland, being near water sounds that much more enticing, so hop back in the rental car and drive south for a couple of hours until you reach the coastal part of Tuscany, known as the Maremma. Though the area is a popular weekend destination for Tuscans and Romans, it’s less well-known to tourists, who tend to gravitate toward big-name towns along the Amalfi Coast or Cinque Terre.
When you’re ready to unplug Italian-style—that is, to spend lazy days at the beach and embrace aperitivo culture—you’ll want to park it in Porto Ercole. Set on Monte Argentario, the town is known for its beautiful, rugged stretch of coastline (and as the final resting place of Baroque bad-boy painter Caravaggio).
Once you arrive, you could easily leave your rental in the hands of the hotel’s valet and spend your time flitting from the pool to the beach. But art lovers will want to visit the Giardino dei Tarocchi (or Tarot Garden) in the village of Capalbio. The monumental sculpture garden is the life’s work of French-American artist Niki de Saint Phalle, who created a series of massive sculptures of figures from the tarot deck covered in colorful mosaic tiles inspired by the ones at Park Güell in Barcelona.
Stick around for a lazy lunch at La Dogana, a rustic-luxe beach club, and walk it off with a stroll in the hilly historic center of Capalbio, which is designated one of the Borghi Più Belli d’Italia (most beautiful villages in Italy). If you’re feeling more ambitious, skip little Capalbio entirely and make the roughly hour-long drive east to the historic city of Viterbo. There, you can pick up a private tour of the hulking, Gothic-era Palace of the Popes, which served as the papal seat back in the 13th century.
Hotel Il Pellicano
Where to Stay in Maremma
For decades, Hotel Il Pellicano has remained the place to be. It’s where Slim Aarons photographed the jet set of the 1960s, and it retains those same retro-glam vibes today. It also features a pool overlooking the sea—but the new kid in town is La Roqqa, where sleek, modern design is punctuated by statement furniture by venerated Italian designers like Gaetano Pesce. The hotel has a free shuttle to bring guests to its Isolotto Beach Club, where the first rows of cushy sun beds are reserved for hotel guests and you can sip rosé and nibble focaccia with burrata for lunch.
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