Experience Luxury at the Best Tuscan Hotels and Villas

Changing Landscape in Tuscany’s Hotel Industry

A host of high-end hotels are changing the landscape in this rural corner of Italy. When I began reporting on Italy’s travel scene in the mid-1990s, Tuscany was considered an alternative destination. In just two decades, that stunning, UNESCO-listed stretch of Tuscan countryside has shifted from an ultra-niche walking and cycling destination to an Italian El Dorado. Since 1998, the number of luxury hotels in Tuscany has dramatically increased.

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 this also applied to the service. Rental villas were commonly the choice, chasing the kind of idyllic experience immortalized in Frances Mayes’s 1996 book Under the Tuscan Sun. However, rental villas can be a lot of work, even if they come with staff. The pandemic accelerated this trend, leading to a surge in guests, particularly those from Italy and elsewhere in Europe.

La Pescaia Resort: The Laid-back Face of the Maremma

The Maremma is as much a mindset as a place. La Pescaia, which opened in stages between 2015 and 2018, was one of the first hotels to nail the area’s sunny, surf-and-turf elegance. Sisters Beatrice and Margherita Ramella transformed it from a farm and horse-breeding estate to a full-scale resort, with fourteen guest rooms enfolding a courtyard shaded by umbrella pines and a century-old Lebanon cedar.

Breakfast and lunch are served on the patio of the 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.

Castello di Casole, A Belmond Hotel, Tuscany: The Story of a New Beginning

In February 2018, Belmond added the hilltop Castello di Casole to their Italian portfolio. Once owned by the brother of film director Luchino Visconti, this 4,200-acre estate centers on an imposing 10th-century castle. Guests can absorb one of Tuscany’s most spectacular sunset views from the infinity pool beneath the castle.

Belmond has meticulously restored the castle and surrounding estate buildings, now housing 39 guest rooms, a cocktail bar, and a restaurant that offers breathtaking views, thanks to an all-weather terrace. Much of what was already exceptional here has been retained, including head chef Daniele Sera’s commandingly good versions of classics like spaghetti al pomodoro and Tuscan fish soup.

Castello Di Vicarello: Exquisite Taste, With a New Generation at the Helm

The Castello di Vicarello resort was a trailblazer when it opened in 2003. The astonishing location: an isolated medieval castle on a rocky spur dominating southern Tuscany. Co-owner Aurora Baccheschi Berti transformed the interior from heavy Tuscan antiques to a stylish, Asian-influenced look.

With the couple’s sons now in charge, the once-clubbish environment has become more inclusive. The atmosphere is more polished, and the addition of two new suites— the tower suite and the spa suite— brings the total accommodations to nine. Vicarello’s appeal is further enhanced by a loyalty to the surrounding area that extends to a menu centered on organic ingredients, complemented by cooking classes, wine tastings, or truffle hunting experiences.

Monteverdi Tuscany: Village Life, Curated

Once semi-abandoned, the tiny village of Castiglioncello del Trinoro was saved from decline by Michael Cioffi, who began purchasing its ancient stone houses. Now, accommodations are scenically dotted around this hamlet. Designer Ilaria Miani has created stunning interiors that utilize local craft traditions.

Monteverdi is in a constant state of evolution: 10 suites added between 2018 and 2020, with upgrades to the spa and the upcoming opening of Zita, a farm-to-table osteria. Run with cultural and commercial motivation, every aspect of the property is Instagram-ready, while Cioffi’s support for local communities enhances the experience.

Borgo San Felice: A Tuscan Veteran Gets a Makeover

Borgo San Felice, originally a settlement, reopened after three years of renovation, transforming into a luxury Relais & Châteaux resort. This working wine estate boasts fifty rooms and suites, featuring a contemporary yet traditionally Tuscan décor.

Grapes are still off-loaded near the main piazza, while a horticultural project pairs diversely abled youths with retired farmers. Culinary offerings include a Michelin-starred restaurant helmed by chef Juan Quintero, who showcases dishes steeped in Tuscan tradition.

Rosewood Castiglion del Bosco: The “Ne Plus Ultra” of Tuscan Estate Hotels

Opened in 2008, this hotel within a historic estate was initially conceived as a private club. However, with Rosewood’s management in 2015, it became the benchmark for Tuscan estate hotels. Dating back eight centuries, the property boasts a charming borgo that offers 23 roomy suites and 11 villas, some with private pools.

Recent enhancements include the arrival of chef Matteo Temperini and the addition of nineteen suites along with a panoramic infinity pool. Guests can wander through stunning landscapes, perhaps on a truffle-hunting expedition, without ever leaving the estate.

Borgo Santo Pietro: The Tuscan Dream, Distilled

Once a run-down estate, Borgo Santo Pietro opened in 2008 as a boutique hotel. Danish owners Jeanette and Claus Thottrup invested years restoring the property, which now features an estate with a small farm and an herb house.

With a culinary emphasis on farm-to-table initiatives, the resort’s 300-acre working estate encourages guest interaction. Antique décor complements a beautifully landscaped experience that feels like stepping into a different era.

Vitigliano Relais & Spa: The Villa That Thinks It’s a Hotel

Vitigliano, an 11th-century farm transformed into a boutique hotel, uniquely offers whole-property bookings while providing high-end services. The exquisite blend of décor and modern amenities allows for a seamless experience in the heart of Tuscany.

With a focus on relaxed luxury, guests can enjoy meals prepared by a resident chef while enjoying stunning views from each corner of the property.

The Best of the Rest

Borgo Pignano: Near Volterra, this mineral estate offers an array of accommodation options alongside fine dining centered on organic produce.

COMO Castello del Nero: This historic Chianti estate beautifully combines Renaissance frescoes with a modern aesthetic and offers relaxation opportunities in its luxurious setting.

Villa Fontelunga: A charming atmosphere combined with unique design makes for an inviting environment perfect for gatherings or special occasions.

Borgo 69: Clustered around a large swimming pool, this project by the creators of Villa Fontelunga captures the essence of new Tuscan country style.

Il Borro: A charming village-turned-resort, boasting various luxurious accommodations nestled within a beautifully designed estate.

La Bandita Townhouse: This boutique hotel offers a cool ambiance paired with an exceptional dining experience featuring local ingredients.

L’Andana: Renowned for its culinary excellence, this five-star resort is deeply rooted in local traditions while offering a modern, stylish experience.