8 Gorgeous Tuscan Villas and Hotels for Your Next Italy Trip, May 2021

Editor’s Note: Travel might be complicated right now, but use our inspirational trip ideas to plan ahead for your next bucket-list adventure. Those who choose to travel are strongly encouraged to check local government restrictions, rules, and safety measures related to COVID-19 and take personal comfort levels and health conditions into consideration before departure.

In the 90s, wine regions like Chianti were better served, but even there, the default option was the agriturismo, a farm that takes in paying guests. Simple was the watchword—and that applied to the service, too. Where you were most likely to stay back then was in a rented villa, chasing the kind of idyll immortalized in Frances Mayes’s 1996 book Under the Tuscan Sun and the film that followed. But rental villas can be a lot of work, even if they come with staff. If anything, the pandemic has accelerated the trend and led to a surge in guests—particularly those from Italy and elsewhere in Europe.

“Last year was a boom season for us,” said Margherita Ramella of La Pescaia Resort, a hotel in southern Tuscany, “and 2021 is shaping up to be even better. People are looking for places away from the crowds, with lots of alfresco corners to relax in.”

One popular model to emerge over the past decade or so involves a hotelier taking over a depopulated village, or a cluster of farm estate buildings, and reimagining it—often complete with a trattoria, a bar, even its own shops. Sometimes this “borgo” is at the center of a large, still active agricultural estate, as at Castiglion del Bosco, Castello di Casole, or Borgo San Felice—the latter being one of the few estate resorts to open its doors before the turn of the millennium. At around that time, some smaller properties also made their debuts—boutique charmers like Castello di Vicarello, Borgo Santo Pietro, Fontelunga, and the Val d’Orcia bolt-hole La Bandita.

But even in the years that have passed since that first wave of resorts in the region, there’s been an evolution. It’s been driven partly by the fact that growing numbers of guests are old Tuscany hands who don’t want to stay in a gated community that insulates them from artisans, village bars, wineries, and summer festivities.

The Tuscan country hotel 2.0 is increasingly permeable—but also increasingly aware that its guests may arrive making comparisons with similar resorts all over the world, from Chile to Bangkok. Simply offering a suite decorated with faded Renaissance frescoes is no longer enough—today’s travelers expect world-class service and amenities, too.

What follows is my pick of the properties that are either new to the scene or have made big changes in recent years. I also offer a list of honorable mentions. All conjure up their own dream version of Tuscany. But in this region where landscape is culture, where ever since the Medicis a virtuous feedback loop has existed between locals and visitors, dreams are often indistinguishable from the real thing.

The Maremma is as much a mindset as a place. For the Tuscan aristocrats who owned estates on this southwestern swath of coastal dunes and agricultural hinterland, it was a Wild West of the heart, a place of cattle-herding ranch hands, long summer lunches, and winter hunting parties. La Pescaia, which opened in stages between 2015 and 2018, is the first hotel to nail the area’s sunny, surf-and-turf elegance.

Sisters Beatrice and Margherita Ramella originally came here from Milan to sell a property that belonged to their father. But they fell in love with the place, and ended up transforming it from a farm and horse-breeding estate to a full-scale resort. Fourteen suites and guest rooms (with four more in the pipeline) and a pair of apartments enfold a courtyard shaded by umbrella pines and a century-old Lebanon cedar. Inside, tasteful antiques chime with period tiles, while just-cut flowers and the airy curtains that billow from four-poster beds keep the mood light and graceful.

Breakfast and lunch are served on the patio of a new-for-2021 bar, while dinner takes place on the terrace of the main villa. The cooking is all seasonal, with much of the produce coming from the estate’s organic garden or trusted artisanal producers. pescaiaresort.com; doubles from $242.

In February 2018, Belmond added the hilltop Castello di Casole to an Italian portfolio that includes Villa San Michele, just outside Florence, and Splendido, in Portofino. Once owned by the brother of film director Luchino Visconti, this 4,200-acre estate west of Siena centers on an imposing 10th-century castle. From the cool expanse of an infinity pool beneath it, guests can absorb one of Tuscany’s most spectacular sunset views, with cypress-studded hills receding to an amber horizon.

The Castello was formerly run by Timbers Resorts, as what was essentially a time-share operation with a 39-room hotel attached, and Timbers continues to manage a number of villas and farmhouses dotted around the property. Belmond has meticulously restored the castle and surrounding estate buildings, which now house 39 guest rooms, a cocktail bar, and a restaurant that finally takes advantage of that view—thanks to a new all-weather terrace. Much of what was already good here has been retained, including Daniele Sera, the head chef at its Tosca restaurant, who, rather than do anything too fancy, pulls off the more difficult feat of delivering commandingly good versions of classics like spaghetti al pomodoro and Tuscan fish soup.

But there’s a new sheen to the service, and the activity schedule has been expanded to include experiences like stargazing in the garden amphitheater while comfortably horizontal. A similar effect can be achieved by overindulging in the excellent cocktails served up in the resort’s chicest corner, the Bar Visconti. belmond.com; doubles from $760.

When it opened back in 2003, the Castello di Vicarello resort and wine estate was a trailblazer. The location was sublime: an isolated medieval castle on a rocky spur that dominates a belt of southern Tuscan countryside with distant views of the sea. But the real surprise was inside. Part of it was visual. Co-owner Aurora Baccheschi Berti, who had shuttled between Bali and Milan with her husband, Carlo, rejected all those heavy Tuscan antiques in favor of a stylish, Asian-influenced look.

The other ingredient was social. To visit Vicarello was to drop in to a house party hosted by two affable yet opinionated aristocrats. The only issue? Guests who didn’t feel like joining in the fun didn’t always feel at home.

Cut to 2021. With the couple’s sons, Neri and Brando, now in charge, the clubbish feel has been dialed back to make the atmosphere more inclusive. Service is much more polished, while two new rooms—the delightful tower suite and the quirky spa suite, which has its own hammam and sauna—have been added, bringing the total to nine.

In my opinion Vicarello is now damn near perfect, its appeal enhanced by a loyalty to the surrounding area that extends to chef Kevin Fornoni’s terroir-based menu, centered on organic ingredients from the garden and from small local producers, all served on a panoramic raft of a terrace above the castle walls. Those same artisanal producers can also be visited as part of a food tour in a vintage Fiat 500 the hotel recently acquired for guests’ use. castellodivicarello.com; doubles from $790.

For years, the tiny village of Castiglioncello del Trinoro, on the edge of the Val d’Orcia, lay semi-abandoned. It was saved from slow decline by Michael Cioffi, a Cincinnati lawyer who began buying up its ancient stone houses almost two decades ago. Today, guest accommodations are dotted scenically around a hamlet that is still home to a handful of permanent residents.

Rome-based designer Ilaria Miani has put her stamp on the interiors, making use of local craft traditions and materials and adding surprising touches. (An aperture in the wall of one bathroom is baffling until you realize it provides amazing views from the shower.)

Monteverdi is in a constant state of evolution: 10 new suites were added between 2018 and 2020, and last year’s shutdown offered another opportunity for an upgrade. The reboot’s star feature is the addition of the Spa & Regenerative Clinic; there’s also a new casual farm-to-table osteria, Enoteca, to complement the existing fine-dining restaurant, Oreade. Both are under the aegis of Italian-American chef Giancarla Bodoni, who also steers Monteverdi’s Culinary Academy.

When it reopens in July, Monteverdi will have 18 rooms and suites, plus three rental houses that sleep anywhere from four to 12 people. Every corner of the place is crying out to be Instagrammed, but what makes Monteverdi stand out is the fact that it’s clearly run by someone whose driving force is as much cultural as commercial. Cioffi has sponsored an archaeological dig on the site, makes a policy of training and employing locals whenever possible, and frequently hosts free concerts, symposiums, and other art events. monteverdituscany.com; doubles from $1,033.

It says something about Tuscan pride, taste, and building standards that farmworkers’ housing should lend itself so readily to becoming a luxury Relais & Châteaux resort, but so it has proved at Borgo San Felice. This once-thriving settlement on a big estate in the heart of the Chianti Classico wine region, which opened as a hotel in 1990, is once again ready for prime time after a three-year renovation that added 11 guest rooms and suites, bringing the total to 60. The previously rather staid décor was refreshed by design studio ArchFlorence in a style that exudes Tuscan heraldic class, but is also bright and contemporary (the capacious spa, housed in the former olive mill, is a particular delight).

Grapes are still off-loaded near the main piazza of this working wine estate, while the Borgo’s agricultural remit is combined with a social mission in a horticultural project that pairs diversely abled youths with retired farmers from the area. The resort’s informal Osteria del Grigio and the Michelin-starred fine-dining restaurant Poggio Rosso are both helmed by young Colombian chef Juan Quintero, who pays homage to hearty Tuscan traditions in dishes like a risotto with wild boar and black kale. And Borgo San Felice has another new arrow to its quiver. It poached one of Italy’s most professional general managers—Danilo Guerrini, formerly of the legendary Tuscan seaside resort Il Pellicano—who has taken standards of service to the very highest level. borgosanfelice.it; doubles from $618.

Launched in 2008, the accommodation arm of fashion scion Massimo Ferragamo’s vast Brunello di Montalcino wine estate in the Val d’Orcia was initially conceived as a private club, where suites and villas would be used by members. A financial crisis put a stop to that idea, but there was a silver lining. In 2015, Rosewood took on its management, and today Castiglion del Bosco is the benchmark example of the Tuscan estate hotel.

Dating back eight centuries, the property centers on the borgo: a small village where workers’ accommodations, stables, and a winery were initially converted into 23 roomy suites. Interiors are done in an elegant Tuscan country style with a vaguely French touch; that aesthetic extends to the 11 villas on the estate, some within walking distance of the borgo, some up to three miles away.

Open all year, unlike the suites (which operate from around Easter until mid-November), these three-to-six-bedroom refuges, most with fireplaces and private pools, are the ultimate venue for a family or group of friends. Two recent updates have raised the resort’s already strong game.

One is the arrival of Matteo Temperini, a fiercely talented Tuscan chef who made a name for himself when he guided the restaurant of Amalfi Coast hotel Le Sirenuse to its first Michelin star. The other will be the July unveiling of 19 new suites and a panoramic infinity pool—the resort’s second—on a hillside site next to the borgo. But what really makes Castiglion del Bosco special was there from the start: it’s a stunning slice of Tuscany 40 times the size of Vatican City, where you can wander all day—perhaps on a truffle-hunting or foraging expedition—without ever leaving the estate. rosewoodhotels.com; doubles from $854.

I’ve never had the chance to travel back in time to the late 19th century for tea with Lady Paget, Vernon Lee, or one of the many northern European and American aesthetes who saw Tuscany as their spiritual home. But a visit to this delightful resort southwest of Siena feels like the 21st-century equivalent.

When its Danish owners Jeanette and Claus Throttrup bought the place in 2001, it was a run-down estate centering on an abandoned 13th-century villa. After seven years of restoration and a landscaping effort that saw thousands of plants brought in, Borgo Santo Pietro opened in 2008 as a six-room boutique hotel with interiors by Jeanette, who deployed antiques, salvaged floors, and sensuous textiles in a gloriously theatrical blend.

The property has since expanded to encompass 22 rooms and suites, 13 of which are in stand-alone buildings scattered around the gardens. There’s a symbiosis between the resort, its three farm-to-table restaurants (one, new for 2021, is a pop-up in the vegetable garden), and what is an increasingly diversified 300-acre working estate that guests are encouraged to visit.

There is a small farm with sheep, pigs, chickens, and alpacas; vineyards and kitchen gardens; a cooking school hosted by a local nonna; an herb house; and a cheese-making factory. Jeannette’s organic Seed to Skin skin-care line provides the bathroom amenities and serves the hotel spa. A perfectly framed vista greets you at every turn—it’s the kind of place where even the painted chicken coops inspire real estate envy. borgosantopietro.com; doubles from $681.

From a cabana next to the ice-blue pool at Vitigliano, the view takes in Tuscan hills cloaked in dark woods and vivid green patches of vines. As you sip a glass of wine, your thoughts might turn to the heavy responsibilities that come with a Tuscan villa rental. Things like cooking dinner, washing dishes, keeping things tidy.

No need to worry about that here. Vitigliano, an 11th-century farm in Chianti that was converted into an eight-suite boutique hotel in 2015, now offers the best of both worlds. In 2019, its owners decided to accept only whole-property bookings, but retained most of the services of a high-end resort.

The décor is a refreshing mix of high and low—Murano chandeliers hang from weathered ceiling beams and flea-market items sit next to original Bauhaus pieces. There’s a small hammam and a dungeon of a wine cellar with some stellar bottles, all available at near cost price, on the honor system. Enjoy them at dinner made by your resident chef—perhaps house-made fettuccine with guanciale, pecorino, and a light snowfall of black pepper. Now all you need to do is talk some friends into sharing the place with you. vitigliano.com; villa from $582.

Borgo Pignano: Located near Volterra, this property follows the classic model of a refurbished farming hamlet centered around an 18th century villa, with a rather fine restaurant that leans heavily on the resortf arm’s own organic produce. Noblesse obliges on a 750-acre estate with an embarrassment of accommodation options. There are 14 rooms and suites in the main building, plus several standalone properties on the grounds, including the new two bedroom villa La vandaia, which has a private pool. The décor throughout is reassuringly old-school, even grandmotherly—if your grandmother happens to be a contessa, that is. Doubles from $423.

COMO Castello del Nero: Taken over by Christina Ong’s COMO group ahead of the 2019 season, this 50-room property felt, on an August2019 visit, like it hadn’t quite ironed out all the creases—especially on the service front. Its 2020 closure in the face of the pandemic nixed a return visit. But this historic Chianti estate, with its Renaissance frescoes, formal gardens, and pared back, airy bedrooms courtesy of Italian designer Paola Navone, is still a lovely setting for a week of rest and relaxation. The resort’s Shambhala Retreat Spa—one of the few in Tuscany worthy of the “spa resort” name—will be fully up and running in time for the start of the 2021 season. Doubles from $847.

Fontelunga: Owner-managers Paolo Kastelec and Philip Robinson created a benchmark for the new Tuscan country-house hotel when they opened in 2000/ It wasn’t just the flair and fun of Robinson’s bold, old-meets-new design scheme that charmed, but the fact that whenever you arrived, you felt as though you’d walked into a party. Doubles from $269.

Borgo69: Just half a mile from Fontelunga lies Kastelec andRobinson’s new project. Here, 12 one-, two-, and three-bedroom villa suites straight out of a coffee-table book on “new Tuscan country style” cluster around a huge swimming pool and vegetable garden. A nearby farm building has been imaginatively converted into the Emporio di Ines, a deli-restaurant and store showcasing local artisanal food producers. Doubles from $330.

Il Borro Ferruccio: Ferragamo’s estate near Arezzo, which centers on a crazily cute village turned resort, unveiled 20 new suites in 2019, housed in a series of converted Medici era farmhouses. Doubles from $415.

La Bandita Countryhouse: In a stunning, isolated hilltop location in the Val d’Orcia, you’ll find this minimalist eightroom temple to contemporary Tuscan chic, where New York creatives and international sophisticates lounge around a pool with the most stunning view. Doubles from $305.

La Bandita Townhouse : In 2013, La Bandita’s owner, John Voigtmann, exported the formula to this second location, set in a former convent in the nearby Renaissance town of Pienza. A highlight of this cool boutique hotel is the restaurant, presided over by Scottish chef David Mangan, who wrangles super-fresh local ingredients and traditions into delicious dishes all his own. Doubles from $360.

L’Andana: This place gained fame as the Tuscan outpost of French super-chef Alain Ducasse, drawing a gourmet crowd to a five-star resort amid the sweeping coastal vistas of the Maremma. Ducasse has since said adieu, replaced in 2016 by Enrico Bartolini, one of Italy’s most dynamic and irrepressible culinary talents. The hotel now holds one of the nine Michelin stars awarded to Bartolini’s six Italian restaurants. Food aside, L’Andana is a smart, 47-room country resort with a stylish urban edge, thanks to the interior design of former AD Italia editor Ettore Mocchetti. But the place is still deeply rooted in the traditions of the area—as reflected in the activities, which include cooking classes, wine tasting, and horseback riding.. Doubles from $435.

A version of this story first appeared in the May 2021 issue of Travel + Leisure under the headline Choose Your Own Tuscan Adventure.