How to spend a winter weekend in Tuscany

February 13, 2022, 12:30 PM UTC

When most people think of visiting Tuscany, it’s assumed that summer is the best time of year to visit. And that’s been reaffirmed in literature and cinema from A Room With a View to Under the Tuscan Sun to Succession.

Thankfully, not only do you not have to be as wealthy as a member of the Roy family to truly savor Tuscany, but the Italian wine region is enjoyable to visit year-round. The little secret no one tells you: winter is a great time to visit Italy—but also Europe, in general—as there are less crowds matched by much better deals on popular hotels and resorts. (Not to mention the summer heat can be truly oppressive.)

If you’re flying in, Florence is your best bet as an arrival and departure point. (Rome is a possibility, too—especially if you’re sticking closer to the most southern part of Tuscany and plan to rent a car or take the train.) And remember: vaccinated U.S. visitors must bring their CDC cards—everywhere from the hotel to museums to cafés—as this will serve as the equivalent of Italy’s “Super Green Pass” while vaccine mandates are in place.

So while in Toscana, here is a brief guide to the wineries and related sights you should visit.

Ponte Vecchio bridge
Ponte Vecchio is a must-see at any time of year, but it is far easier to walk around with more breathing room during the off-season.
Rachel King

Where to stay

Hotel Brunelleschi: If Florence is your home base, then nowhere is better situated than the Hotel Brunelleschi, just steps away from all the major sights, including the Uffizi Gallery and Ponte Vecchio in one direction and the Cattedrale di Santa Maria del Fiore (a.k.a. the Duomo) in the other. And while it might look partially like a medieval castle from the outside, it’s all modern luxury on the inside with a chic hotel bar, bright breakfast buffet salon, a high-tech fitness room complete with Technogym treadmills, and lightning fast Wi-FI throughout the hotel.

Albergo Le Terme Spa and Hotel: Once you’re out in the countryside, the Albergo Le Terme Spa and Hotel in the charming village of Bagno Vignoni is a literal hotspot. That’s because this 15th century palace (once used as a summer residence by Pope Pius II) is sitting on top of a large thermal bath dating back to the Etruscan era from which water flows at 49 degrees Celsius (120 degrees Fahrenheit). Guests can enjoy the waters at a more comfortable level at the whirlpools within the hotel.

Relais dei Molini: When most people think of going to Tuscany, they most likely consider the iconic rolling hills farther inland rather than staying by the beach. But the Mediterranean coast is enjoyable year-round, and nowhere has a better view than the Relais dei Molini. Recently renovated, this bed and breakfast has just seven rooms, including multiple suites with full bedrooms and living rooms, and you have all the modern comforts (Wi-Fi, TV, coffee machines in the rooms, etc.) with prime access to both the mountains and the beach.

Gucci Osteria restaurant
Inside Gucci Osteria da Massimo Bottura, a Florentine restaurant with two Michelin stars.
Rachel King

Where to go

Salvatore Ferragamo Museum: Certainly, if you’ve never been to Florence, you have to hit up the usual tourist spots like the Pitti Palace and the Duomo. While the crowds will definitely be thinner during the off-season winter months, there are always other options off the beaten path. Fashionistas should not miss the Museo Salvatore Ferragamo, dedicated to the life and work of the illustrious Italian shoe designer—who settled in Florence and died there in 1960—and his eponymous label. The museum hosts a rotation of exhibitions on themes close to the designer. The current exhibition, “Silk,” showcases numerous patterns from cultures worldwide throughout history that have influenced the house’s signature silk neck scarves and men’s ties.

Tempio del Brunello: If you’re eager to go wine tasting, but know little about Tuscany—especially about Brunello di Montalcino, a red wine made from sangiovese grapes and one of the flagship wines of the region—then this museum is a good place to start. Located in the heart of Montalcino, an enchanting town perched on a hilltop in the middle of Tuscany, the Tempio del Brunello offers a multi-sensory experience, guiding visitors through a tour about the history and culture of the region and the winemaking process. At the end of the tour, be sure to stop into the Bistrot wine bar, which has an interactive showcase asking visitors a number of questions regarding their temperament and character in order to then guide them in choosing the Brunello best suited to their personalities.

Castello di Castiglione della Pescaia: Castiglione della Pescaia is a popular seaside resort town along the coast of southern Tuscany in an area known as Maremma. Here you can get the best views of the Mediterranean and the island of Elba from the Castello di Castiglione della Pescaia, a fortified settlement dating back to Roman times.

Castello di Volpaia vineyards
The vineyards at Castello di Volpaia at sunset.
Rachel King

Where to eat

La Sosta: Being in the heart of one of the world’s most prominent wine regions, Montalcino has no shortage of places to eat—let alone Michelin-starred restaurants from which to choose. But all those choices can become overwhelming. A suggestion: La Sosta is a modest, cozy wine bar and restaurant where you can feel comfortable asking all of the questions you might have about wine and food pairings. A bonus: There is often live music during dinner.

Enoteca Pitti Gola e Cantina: If you’re looking for a leisurely spot not too far from the bustling center of Florence— but still a little calmer—then this is it. Not to mention this elegant bar and restaurant has a deep, deep catalog of vintage wines dating back decades. This is definitely a place to splurge, but also experiment and have fun with some old bottles.

Gucci Osteria da Massimo Bottura: A meal here is an Experience, with a capital E, from start to finish. The interior of the restaurant is a feast for the eyes, with lime green walls and dark teal tufted banquettes, making you feel like you’re sitting inside a precious jewel box. (And if you find yourself in love with the colorful dining china, yes, you can buy a set for yourself.) But the food is just as fanciful as the decor, thanks to chef Karime Lopez, a Mexico City native whose resume includes Pujol in her home city and Osteria Francescana in Modena, Italy, the world-famous restaurant of chef Massimo Bottura. Guests can choose between two tasting menus with wine pairings or plates à la carte. The kitchen is very accommodating of dietary restrictions with multiple vegan and vegetarian alternatives available by request. As you would to any meal in Italy, come prepared—that is, come hungry—because you will not leave hungry.

A side street in Montalcino, Tuscany, Italy
You should give yourself some extra time to explore the fortified town of Montalcino, which is in the heart of Tuscan wine country.
Rachel King

What to drink

Castello di Volpaia: Perched on a hilltop just north of Radda in the heart of Chianti Classico country is the village of Volpaia, established in the 12th century. The vineyards belonging to Castelo di Volpaia‘s winery are spread across roughly 45 hectares (112 acres) at more than 400 meters (1,312 feet) above sea level. This is also a great spot to stay overnight as the estate recently renovated its suites, featuring comfortable bedrooms and spotless marble bathrooms with amenities such as high-speed Wi-Fi and HDTVs. The suites are available by the night and can be reserved by the week if you want to spend more leisure time within the surrounding area.

When going in for a wine tasting, reservations are required—not just because of COVID but open hours fluctuate throughout the year, depending on the high versus low seasons among tourists. When tasting, start with the 2020 Chianti Classico, featuring predominantly sangiovese grapes and just a tiny percentage (10%) of merlot. Aged for only one year, this wine isn’t too heavy, with soft tannins and a smooth mouthfeel. Follow that up with the 2018 Chianti Classico Gran Selezione, initially classified as a Super Tuscan, made with 100% sangiovese grapes. A little more subtle, this wine is full of classic red fruit on the palate.

CastelPrile: CastelPrile is Volpaia’s sister property in Maremma, which is introducing a new cru wine in early 2022 in line with an overarching rebrand. The growing season starts much earlier on the coast—not only because of the types of grapes but also because the weather is very different from two hours inland. Vermentino and cabernet sauvignon grapes, in particular, do well in this coastal micro-climate. Considering how quickly the weather is changing, many winemakers are strategizing how to slow down the ripening process. At CastelPrile, this has prompted a replanting of the vineyards—a major investment—and currently the winery is on track to replant up to three hectares per year of plants over 12 hectares.

Future visitors should not miss the 2021 Campione da Vasca Vermentino, being released this year. Vermentino needs to breathe the salinity of the seaside, which is why, within Italy, you often find it in Sardinia or Liguria, but now more and more in Tuscany (at least when closer to the sea). This vermentino wine has a nice minerality, an open nose, and a smooth mouthfeel, making for a very fresh wine at a young age.

Also worth your time is the 2020 CastelPrile Cabernet Sauvignon. In Italy, winemakers almost always consider how the wine is paired with food rather than for standalone consumption. Made from 100% cabernet sauvignon grapes, the 2020 vintage was a particularly good one for the house, with a nice structure in the mouthfeel and perfect balance with almost any food (even white fish—seriously). It’s not super dense like most New World cabs, especially those made in the United States. There is a ripeness is almost perfect, and it is soft enough that it could withstand being chilled for summer consumption.

There is no cellar on-premises; grapes are harvested during the night when its cooler and brought to Volpaia for production. Tastings can be arranged by special request. Alternatively, the house on-site—with a full kitchen, living room, and multiple bedrooms and bathrooms (can sleep up to 14 with kids doubling up in rooms)—is available to rent during the summer. And if you want to avoid the crowds at the beach, there is an infinity pool with views of both the vineyards and the sea.

Tenuta Sette Cieli at sunset
Bordeaux varieties are the core production at Tenuta Sette Cieli, with the small exception of one hectare of sangiovese planted in 2016.
Rachel King

Tenuta Sette Cieli: Translating to “Estate of Seven Skies” in English, Tenuta Sette Cieli produces fine red wines only with all of the finest grapes with which you’re probably already familiar—especially cabernet sauvignon, cabernet franc, merlot, and malbec. Like all other winemakers in the region, the house has dealt with hotter vintages each subsequent year since 2015. But unlike other wineries nearby, Sette Cieli’s natural advantage is its elevation, also at 400 meters above sea level. For example, during the summer of 2021, temperatures at sea level hovered as high as 40 degrees Celsius (104 degrees Fahrenheit), while up in the hills at the vineyards, temperatures only reached 33 degrees Celsius (91.4 degrees Fahrenheit).

The region has had its share of extreme weather in the last few years, including a major rainstorm right before the harvest season in September 2017, which caused major flooding to the point where the soil could no longer absorb the water. The winery was able to salvage at least half of its grape production for its 2017 Indaco, a blend of cabernet sauvignon, malbec, and merlot. While the ratio of grape varieties is split three ways, the resulting wine has the typical aroma and powerful mouthfeel of malbec with velvety soft tannins and deep notes of red fruit on the mouthfeel.

Val di Suga: If you have plenty of time, consider an afternoon at Val di Suga, just at the base of Montalcino, which hosts a splendid tasting room filled with sunshine and panoramic views of the rolling hills dotted with cypress trees. Val di Suga has a deep catalog of Brunello di Montalcino—among them, the 2013 and 2016 Vigna Spuntali Brunello di Montalcino are sure crowd-pleasers for almost any palate, and are more approachable than most Brunellos. The 2016, especially, is the embodiment of a Mediterranean red wine in a bottle. On the nose, you might pick up notes of sand, but in the best way possible—this is a red wine you could drink at the beach. The 2020 Rosso di Montalcino is also very easy to drink, produced as a traditional vintage with a soft, minimalist style—clean on the nose and fresh on the palate.

Biondi-Santi: As one of the most prominent producers of Brunello in Tuscany, the 2017 sale of family-owned Biondi Santi to a French company (Paris-based Européenne de Participations Industrielles, also the owner of Champagne producer Charles Heidsieck) caused quite the stir. But even with the change in ownership, you can still expect the same traditional local approaches to winemaking with innovations introduced only in the name of combatting climate change.

Biondi Santi stands out from its competitors in a number of ways, including that it releases vintages a year later than most Brunello producers as Radi says sangiovese simply needs more time. Future visitors to the estate—which dates back to the 16th century and is regarded as one of the most historic villas in Italy—should not miss a chance at the 2015 Brunello di Montalcino Riserva, a young wine that is ready to drink now so long as you give it long enough to breathe after opening the bottle. A rainy winter and spring allowed the grapes to ripe slowly but in a balanced fashion, resulting in a body that is light but filled with flavors of red fruit.

Sangiovese isn’t always the easiest grape to work with, but obviously there is nowhere better in the world to work with sangiovese than Tuscany. Winemaker Federico Radi stresses it’s all about respecting the land, from the soil to the local forests, to maintain an ecosystem that will produce the same quality grapes (and therefore, wine). “We’re already late on climate change, and we have to do something now to preserve the ground for the next generation,” he says. “We are the guardians of this beautiful landscape, and sometimes we forget that.”

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