Highlights: The grass-edged sunken swimming pool; Bathhouse spa; horseback riding at Taetro Equestre; Accademia di Cucina cooking school; activities such as truffle hunting and wine and olive oil tastings
The Rosewood name is synonymous with luxury and top-tier service, and one of its most breathtaking properties is Rosewood Castiglion del Bosco , nestled in the hills of Tuscany, in the UNESCO World Heritage Site of Val d’Orcia. It’s set within a 900-year-old estate, which Rosewood has painstakingly preserved. And with just 42 suites and 11 villas, there’s privacy in spades. (Fun fact: The estate was owned by the Ferragamo family in the 1970s.)
Guests at Rosewood Castiglion del Bosco have the privilege of taking full advantage of all that the property has to offer, including a cooking school where they’ll prepare traditional Tuscan dishes, an on-site winery, a golf course, and an organic kitchen garden inspired by medieval enclosed gardens. There are painting classes, perfume workshops, day trips to nearby Siena, and you can even take a vineyard tour by helicopter—and the list of experiences doesn’t stop there.
Last but not least, this summer, the resort is offering a new Ferragamo Experience called Made in Tuscany . The day starts with an intimate wine and cheese pairing at the Castiglion del Bosco Wine Lounge , followed by a visit to the Salvatore Ferragamo Museum in Florence and a VIP shopping experience at the Ferragamo flagship store on Via Tornabuoni. Sign me up.
Highlights: Castiglion del Bosco winery; the Spa at Rosewood Castiglion del Bosco; heated, lavender-lined infinity pool with expansive views; A Day at the Farm experience; the two-Michelin-star Ristorante Campo del Drago; La Canonica Cooking School
Located halfway between Florence and Rome in Tuscany’s Maremma countryside, Castello di Vicarello is the epitome of a luxury farmstay hotel. Like many farmstay properties, it’s anchored by a historical building—in this case, a family-owned castle dating back to the 12th century. With only 10 suites , each unlike the other, and a new villa that was once a watchtower, staying in the meticulously restored castle is special, to say the least.
One of the many standout features is the estate’s two marble pools, one an infinity pool overlooking the Tuscan hills and the other a wellness pool nestled among an olive grove. Also on the property is an expansive vegetable garden, olive trees, and vineyards. Guests can choose from a host of activities, including truffle hunting, wine tasting, cooking and cocktail classes, and hiking. You could also opt for a massage in the garden gazebo or your suite. Of the several dining options on-site, you can enjoy farm-to-table cuisine atop the castle at La Terrazza, have a candlelit dinner on the terrace or inside the castle’s glass house, or enjoy breakfast in the courtyard. All in all, Castello di Vicarello is a dream vacation scenario.
Highlights: The marble pools; breathtaking views; the property’s hiking trail; the gardens and vineyards
(Image credit: Salva Lopez; Renee Kemps; Alessio Manca; Alessio Manca/
Masseria Moroseta )
Take a traditional farmhouse and give it a modern update in keeping with the design trends of the 21st century, and you have Masseria Moroseta . This particular property is situated just 15 minutes by car from the Adriatic Sea, so if you can’t fathom vacationing in Italy without a close proximity to water, this is the farmhouse hotel for you.
Masseria Moroseta is located in the Apulia region, which is known for its charming whitewash stone farmhouses, most of which date back to the 16th century. Masseria Moroseta, which has the feel of a cool boutique hotel and is highly Instagram-worthy, is surrounded by a lovely olive grove. The property gets its extra-virgin olive oil from the trees, naturally. Speaking of, the restaurant also uses ingredients from its vegetable gardens, orchard, and chicken coop. But a menu won’t be handed to you upon sitting—they ask that you trust the chef. I certainly would.
Among the activities are cooking classes, Italian motorboats available for day tours or mini cruises, and a handful of weeklong workshops throughout the year. It also manages six homes in the region with a similar aesthetic that are available for booking.
Highlights: Moroseta boats; the kitchen; the olive grove; the architecture; views of the sea
Some of the most special resorts across Italy (and the world, for that matter) bear the Belmond name. And the Tuscany property, Castello di Casole, a Belmond Hotel, Tuscany , might be one of the most special in its portfolio. Castello di Casole is anchored by a medieval castle, built in 998 (yes, that’s a three-digit year), and Etruscan farmer artifacts have been found on the grounds, and in the 1800s, the owners at the time cultivated the land. The property’s expansive views of the region are a marvel.
Each of the 39 suites and two private villas has been restored and updated using original materials found on the estate and is furnished with modern pieces. Stone walls and wood-beam ceilings abound. On the luxury farm estate, you’ll find a full spa, vineyards, state-of-the-art tennis courts, four restaurants, and a hilltop infinity pool. Guests can participate in activities as wide-ranging as stargazing, a focaccia baking session, and yoga classes, many of which are complimentary. (And I got the inside scoop that a photography residency and a brand-new wellness program are in the works.) It’s all a recipe for the trip of a lifetime.
Highlights: Essere spa; tennis courts in partnership with Lux tennis; 25 acres of vineyards; heated infinity pool; Tosca Ristorante
In the heart of Umbria, you’ll find the family-owned Tenuta di Murlo . The luxurious country estate has just three rooms and nine villas on-site, all surrounded by farmland, olive groves, lakes and rivers, gardens, and vineyards. It’s a truly magical place if you’re looking for a private, relaxing eco-retreat where you can embrace all that the Italian countryside has to offer.
Surrounded by medieval Umbrian villages, guests truly feel like they’re transported to another time while at Tenuta di Murlo, but with the modern luxuries that sophisticated travelers have come to expect. As far as activities go, you’ll of course find cooking classes and wine tastings, as well as ceramic classes, paddleboarding in the lake, horseback riding, mountain biking, and in-villa spa treatments. For dining and cocktails, there’s Il Caldaro restaurant housed in an ancient rural hamlet on the property and the wall-to-wall windowed Orangerie bar.
Highlights: The medieval landscape; Il Caldaro restaurant; on-property farmhouse animals and pony ranch; lake views and activities.
In the heart of Tuscany, less than an hour away from the Mediterranean, 30 minutes from Siena, and 90 minutes from Florence, you’ll find the incredibly luxurious Borgo Santo Pietro , which refers to itself as “once a healing stopover for medieval pilgrims.” Today, the property encompasses 300 acres of organically cultivated farmland with alpacas, sheep, pigs, nut fields, vineyards, and an on-site dairy.
There are 22 spacious, antique-filled rooms, some with Mediterranean courtyards, leafy private terraces with outdoor fireplaces, and private pools. At the elegant Borgo Spa , treatments feature its own natural skincare line, Seed to Skin. The restaurants are something to behold at Borgo Santo Pietro, including the Michelin-starred Saporium Chiusdino and Trattoria Sull’Albero, which is designed around a large oak tree. There’s also a pop-up restaurant, Orto, in the vegetable garden during the summer months. To fill their leisurly days, guests can choose from activities as varied as sheep milking and cheese making, art lessons, floristy, and falconry displays. All in all, Borgo Santo Pietro is the definition of a luxurious, immersive Italian farmstay.
Highlights: The many gardens; unique farm activities; Saporium Chiusdino and Trattoria Sull’Albero; Borgo Spa; the breathtaking infinity pool.
One look at Bertarello and you’ll be surprised to hear that when its long restoration began 20 years ago, it was practically in ruins. After being built in the late 1700s as a watchtower, it was repurposed over the centuries as a barn and hayloft and later abandoned. But the owners were able to bring the farmhouse back to life using all of the materials that were left. Today, Bertarello is one of the region’s most cherished boutique luxury farmhouse properties.
Just an hour outside of Rome, Bertarello is closest to the medieval city of Viterbo. It’s also just 45 minutes from the Tyrrhenian Sea, which should be good news for anyone seeking a water excursion. At the estate, chef-prepared meals are served by the fireplace in the intimate kitchen or under the rose gazebo, using ingredients from the organic garden. (Fun fact, they’re known for their olive oil .) In addition to picnics, cooking classes, hikes, and massages, golf lovers can take advantage of the 16 nearby courses. Bertarello is home to just five rooms, each decorated and furnished in an ornate yet rustic fashion.
Highlights: Intimate meals in the kitchen, the feel of staying in a private home; taking part in the olive oil–making process; expansive garden and pool area.
Properties with the feel of the country but with close proximity to one of the best cities in Italy offer the best of both worlds. And if that’s your goal, Torre di Bellosguardo in Florence should be on your radar. The historic 13th-century, independently owned villa overlooks the city and is an authentic example of Tuscan medieval and Renaissance architecture. Initially functioning as a refuge and hunting lodge, it was converted to a hotel during the early 20th century. Gardens, orchards, vineyards, and olive groves outline the charming property, and farm animals are a common sight.
At Torre di Bellosguardo, every detail of a stay is intimate and authentic. As an example, cooking classes are taught by the owner, using produce from the garden and wine from the vineyards. When booking , guests can choose from 16 uniquely preserved rooms and suites, none of which are made to feel like a typical hotel. Guests can enjoy a farm-to-table breakfast on the terrace before a day in the city, lounge with a spritz by the pool, stroll through the stunning gardens with an espresso, and pay a visit to the farm animals. All in all, it provides the perfect relaxing retreat between visits to Florence.
Highlights: Spectacular gardens; proximity to Florence; authentic medieval archtecture; unique guest rooms.
If you’re drawn to the authentic whitewashed farmhouses of the Apulia region, Masseria Palombara is a standout option, to say the least. In the heart of the Salento countryside, at the tip of Southern Italy, it’s just a stone’s throw from the sea. This eco-conscious adults-only property is nestled among olive groves and almond trees and includes all of the luxuries modern-day guests can ask for. There’s a full spa, a cozy restaurant using ingredients from the organic garden, a wine bar, and two pools.
There are 22 rooms and suites at Masseria Palombara , and guests can choose from a host of experiences, including orecchiette making, movies in the open-air cinema, beach excursions, cooking classes, Vespa rentals, and trips to the unique surrounding cities. As you can see, it’s a boutique hotel that offers numerous options for ways to fill your days and nights.
Highlights: The spa; proximity to the sea; outdoor cinema; authentic rural working farmhouse experience.
After booking your Italian luxury farmstay and planning your activites, the next step is figuring out your wardrobe. These properties are casual by nature, but that’s not to say that guests don’t dress up for dinners and such. Central and Southern Italy can get quite warm in the summer, so linen and poplin are key. And don’t forget pack swimsuits, attire that allows for hiking, and shoes that you can successfully navigate the terrain in (as in, cobblestones and hilly farm pathways).
DÔEN
Emmaretta Cotton-Voile Midi Dress
LE MONDE BÉRYL
Regency Woven Leather Ballet Flats
J.Crew
Gwen Lace-Trim Slip Skirt in Linen
Hat Attack
Vented Luxe Packable Straw Hat
Treasure & Bond
Square Satin Scarf
High Sport
Savannah Shorts
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