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Tuscany is one of the few places in Europe that looks pretty much exactly as you’ve always imagined. Rolling hills dotted with vineyards seem to stretch beyond the horizon. Restaurants at every price point offer reliably delicious meals. Excellent wine and olive oil are plentiful and often shockingly inexpensive, and a wrong turn down a narrow street more often than not results in stumbling upon some Renaissance or Etruscan ruin that you never would have found otherwise.
In other words, Tuscany’s riches don’t require much planning. The region is home to remarkable wine producers whose reds have pride of place in serious collections all over the world, the Michelin Guide has anointed a number of restaurants in Tuscany with their coveted stars, and accommodations from casually chic agriturismos to five-star hotels can be found throughout.
As with any renowned region, however, streets are increasingly clogged with throngs of tourists, hotel reservations can be difficult to come by in high season, and otherwise bucolic views in both the countryside and the cities can be obstructed by people, all of them seemingly snapping the same selfie at exactly the same moment.
All hope isn’t lost, however. With the right planning and a reasonable amount of flexibility, you can make Tuscany feel like your own private paradiso. Here’s how to do the region right.
Florence and Siena
Florence is part of Italy’s holy trinity of tourist destinations, alongside Rome and Venice. Amazingly, despite a history that stretches back millennia, there’s always something new and unexpected to discover down one Vespa-buzzed street or another.
A visit to Florence has to start at S. Forno Panificio, a century-old bakery and cafe that not long ago was purchased by the team behind the excellent restaurant Il Santo Bevitore. The inviting, light-filled space is filled with everything you want to eat for a perfect Italian or pan-European breakfast—cardamom-flecked pastries, breads with crusts that shatter into a million pieces at the first touch of teeth, and so much more. Unexpectedly, though, there is no espresso or cappuccino. The only coffee on offer is Americano, but it’s delicious and well-brewed. In addition, over the course of several visits this past summer, every child in the place seemed to be savoring a neon-green minted milk drink called latte e menta. I may or may not have pilfered most of my six-year-old’s cup each time.
Pizzeria ‘O Munaciello on Via Maffia, or the olive-oil-focused Olivia, on the Piazza Pitti, are fantastic places to stop by for a light lunch, followed by gelato at Grom…or any of the other standout gelaterias in the city. It’s a bit of a local game to discover and argue over who makes the most enjoyable flavors. Best to eat as much as you can: It’s research! And no trip to Florence is complete without dinner at La Giostra, the grotto-like restaurant that’s now run by the second generation of the d’Asburgo family. The pastas are transporting, the chocolate sachertorte is decadent—and invented by a d’Asburgo ancestor—and the wine list runs deep.
Florence is a city that wears its history lightly, and contemporary art installations regularly perk up the ancient monuments that grace the covers of guide books. Last year, the artist Tony Cragg had monumental sculptures strategically scattered around the Boboli Gardens. The street artist Clet—think of him like an Italian Banksy, but with works on a generally smaller scale—has transformed countless road signs into slyly humorous graphic art. Another artist, who goes simply by the name Blub, has pieces in cities all over the region: Pasted to walls all over Florence are his modifications of classic paintings and images of famous personalities in which the subjects wear massive goggles. It’s disorienting and charming in equal measure. Lucaworkshop, an antique shop and artist’s studio, bridges the past and present of the vibrant city brilliantly.
Great hotels can be found everywhere in Florence. Villa La Massa, an American Express Fine Hotels & Resorts property, which is a quick ride from the city center in Bagno a Ripoli and sprawls through a 16th-century palazzo, drips with charm and unselfconscious luxury. The four-star Hotel Monna Lisa is also charming, and the rooms, despite modern touches, are firmly rooted in the palazzo’s Medieval past. A negroni cocktail on the patio at sunset is the perfect way to end a day in your thoroughly sophisticated digs.
Siena, whose downtown wraps around the massive Piazza del Campo, is a perfect one- or two-day destination. The annual Palio, comprised of two races held in July and August, is to horse racing as roller derby is to figure skating: A raucous, citywide event that revives ancient rivalries in the most colorful, celebratory way.
Food lovers have to stop by De Miccioli for what may well be the best porchetta sandwich in the world: Sliced by the stoic men who work the counter, I recommend getting it to go, with a beer and sides like olives and marinated artichokes, to enjoy on the steps around the piazza. For a more formal—yet still casual—experience, check out Le Logge, the perennially popular restaurant just off the piazza. Their carbonara is classic, and if you make friends with the server, you may be offered a tour of the wine cellars, located underground and across the street.
During your wanderings in Siena, make sure to stop by Santa Maria della Scala for the archaeological education, the Pinacoteca Nazionale for the Medieval works, and the Museo della Tortura—the torture museum—which my nephews loved. If you’re staying overnight, the American Express Fine Hotels & Resorts property Grand Hotel Continental has become a popular option for visitors willing to spend a bit more, and the Campo Regio Relais, whose six rooms are often in justifiably high demand, is also worth considering.
Pistoia and Lucca
Two of the unsung heroes of Tuscany are Pistoia and Lucca. Skip Pisa and its often disappointed crowds (yes, the tower really leans, and no, it’s not really worth the effort to see it). Instead, carve out at least a day (or two!) to explore each of these unassuming gems.
Pistoia is located less than an hour’s drive northwest of Florence, and even in traffic it’s not likely to take much more than 60 minutes or so to get there. It’s home to one of the largest blues festivals in Europe every summer, and pulls in an impressive range of acts. Ben Harper headlined last year and Elton John performed in nearby Lucca to a capacity crowd. Even aside from the bold-face names, it’s a July festival worth checking out—although postponed this year due to COVID-19. Local and regional jazz and blues bands set up on stages scattered throughout the city, serenading locals and visitors with a diverse range of styles and influences.
Great restaurants can be found everywhere here, from the local favorite La Botte Gaia (their meaty maccheroni pistoiese is unforgettable, and defines stick-to-the-ribs Tuscan cuisine) to Ristorante Cozzeria Pluma, whose wide selection of mussels is one of the best I’ve ever seeing in the entire region. I Salaioli offers a range of fresh-sliced meats and cheeses, as well as a nicely curated selection of wines, pastas, and condiments, in the heart of Pistoia, as well as the option for a sit-down meal both indoors and al fresco. Some of the best gelato I’ve tasted in the region is in town, too: Una Mole di Gelto offers a beautifully chosen list of flavors, and the staff is helpful and kind, no matter how bad your Italian may be. A quick 20-minute drive outside of the city is La Dispensa, where cheesemaking tours take you to the heart of what makes Tuscan sheep’s-milk cheese so wonderful.
Given the history of Pistoia, as well as its vibrant contemporary arts scene, it should come as no surprise that there are countless museums to choose from. The Museo Civico di Pistoia provides an excellent voyage through the city’s history; guided tours are a must. The Museo della Fondazione Marino Marini is a showcase for more modern works, and the rotating roster of exhibits is extraordinary. The sculptural exhibits in particular are worth the visit.
Lucca, located a 45-minute drive to the southwest, is another Tuscan gem. Surrounded by walls that date to the 16th century (though earlier fortification can be traced back to around 200 B.C.) and that are today used by locals and visitors alike as jogging and biking paths, the city center is a maze of winding streets lined with excellent, often affordable restaurants and shops, the gorgeous and imposing Cattedrale di San Martino, and the Casa Natale, where Puccini was born.
Make sure to bring your sneakers: A walk up the stairs to the top of the Torre delle Ore requires some effort, but it’s worth the hike. The top of the clock tower offers gorgeous views of the surrounding countryside, the hills dropping off into the hazy distance.
Beaches and Outdoor Activities
Tuscany is generally associated with its famous rolling hills and the postcard towns perched along their flanks. But it’s a massive region that also boasts a notable coastline that visitors should not miss.
Public beaches can be found, but your best bet is to buy a one-day “membership” to any of the private beach clubs that line the sea. Bagno Concetta, in Forte dei Marmi, offers day passes whose prices vary based on the time of year and how elaborate you’d like the experience to be: Lounge chairs with umbrellas; more private set-ups with a small table and four chairs, all covered by a massive umbrella; private cabins to get changed in and lock your gear away for the day—it’s like a choose-you’re-own-adventure novel set on the shimmering water. The restaurant on-site isn’t inexpensive, but the views look like they were painted by Bob Ross, and the frito misto is among the best I’ve ever had. La Chicca, a five-minute walk away in town, serves miraculous gelato—I’d happily go there even in the dead of winter.
In Bibbona, not far from the legendary Super-Tuscan producer Ornellaia, is La Pineta, a Michelin-starred restaurant whose chef goes fishing most mornings to catch his menu. Their langoustines are game-changing, and rivaled only by the views of the sun setting over the water just outside the windows.
For great daytime relaxation, look to the facilities built around the terme, or thermal springs, that run underneath. The Grotta Giusti is a lovely hotel in Monsummano that offers day passes to its beautiful thermal-spring pool. It boasts clean, welcoming facilities and a large pool whose water will leave your skin glowing more brightly than if you’d just finished a bottle of the local wine.
Bicycling is another popular activity, and bikes can be rented throughout the region. Popular, reliable outfits found in seemingly every city and town make it easy. Hiking tours are also available, and depending on where you are, you’ll be able to explore the mountains, surrounding forests, or farms that sprawl throughout the region.
Where to Drink Wine
Tuscany’s most famous wine is Chianti, but even the most well-versed oenophile will find surprises among the offerings there. Producers like Querciabella, in Greve in Chianti, and Castello di Albola, in Radda in Chianti and set in a magnificent Medieval castle, offer public tours and tastings. Their wines, from Super-Tuscans to age-worthy Chianti Classico Riserva Gran Selezione bottlings, offer excellent value for the quality at every price point. Brancaia, which is also in Radda in Chianti, has fantastic tours and a delicious new restaurant on-site, with all the salumi and pasta you could ever want to eat to fortify you for more tasting.
In the nearby town of Panzano in Chianti, the famous butcher-shop-slash-restaurant Antica Macelleria Cecchini draws carnivorous pilgrims from around the world. The gregarious Dario Cecchini offers three dining experiences, from the steak-centered Officina to the more snout-to-tail focused Solociccia to the more flexible Dario DOC. All three are delicious options, should be washed down with as much local Chianti in straw-covered fiaschi as you can drink (the restaurants provide it), and the first two are fixed price at 50 euros or less, which means you can control exactly how much you spend.
In San Gusmé, Tenuta di Arceno, a Jackson Family property whose wine is crafted by the Bordeaux legend Pierre Seillan (it’s a globalized world, even in rural Tuscany!), guests can sample their phenomenal range of Chianti, Super-Tuscans, and more. Lunch at AnoniMa X, a quick 10-minute drive away in Castelnuovo Berardenga, is a must, as is the tagliatelle with white ragout of the local Cinta Senese pork that they serve there.
The original Chianti recipe was created by Baron Bettino Ricasoli in 1872, and today, the picture-book castle and sprawling estate in Gaiole in Chianti is run by his ancestor, the 32nd Baron di Brolio, Francesco Ricasoli. Their single-vineyard Sangioveses are some of the best in Tuscany, the tour of the castle and grounds will win over kids and adults alike, and the restaurant on the property, the Osteria di Brolio, offers a sophisticated, beautifully presented lunch or dinner.
Ruffino has estates throughout the region, but their center of gravity, the beautiful Tenuta di Poggio Casciano, in Bagno a Ripoli, provides an excellent overview of what makes Tuscan wine so renowned.
More rural and closer to the coast, Maremma is as far from the bustle of Florence and Siena as you can be…at least, that’s how it feels. This is agriturismo country for visitors, and Tenuta Impostino, in Paganico, is one of my favorites. It offers a lovely pool, lots of outdoor activities for the entire family, and a restaurant on-site that serves a wide range of homemade products, from breads and meats to impossibly fresh pastas. A quick drive away is Bracali, a Michelin two-star restaurant whose creative, imaginative riffs on Tuscan classics and beyond is the kind of place that you’ll dream about long after you fly back home.
Il Borro, even if you don’t stay there—but you should!—is owned by the Ferragamo family, and is just as curated and stylish as you’d imagine. They essentially bought a Medieval village and refurbished it, transforming it into the Tuscan town of your dreams. The wines are spectacular, especially the sparkling wine, Il Bolle di Borro, and the restaurant offers a phenomenal take on the famously rustic cuisine of the region. Accommodations run the gamut from apartment-style suites in the rehabbed town itself to entire houses set a quick ride outside, replete with private swimming pools, playground equipment if you’re traveling with the kids, and much more. Leaving there this past summer was one of the hardest things I’ve ever had to do.
Another branch of the famed fashion family owns Castiglion del Bosco, in Montalcino. Their land covers around 5,000 acres, and the accommodations, by Rosewood, are every bit as unselfconsciously chic as at Il Borro. Both the fine-dining restaurant, Ristorante Campo del Drago, and the more casual one, Osteria La Canonica, offer creative, deeply satisfying meals. So do Boccon Divino and Osticcio Ristorante Enoteca, both in Montalcino, which bring together satisfying, creative food and magnificent wine lists.
If you plan well and travel with an open mind, Tuscany is a welcoming, soulful region ready to either confirm your fantasies about it or to confound expectations in the most delicious, welcoming, transformative ways.