Carved into the rocky coastline of Tuscany’s Monte Argentario peninsula, Il Pellicano hotel showcases sea views with old-world pomp.

A Ferragamo family-owned hideaway in Tuscany, Italy, Rosewood Castiglion del Bosco hotel has a golf course, stables and impeccable amenities.

The five-star Castello di Casole comes with a spa, vineyards, three restaurants, a bar, and an epic infinity pool. While it does feel somewhat compounded, that caveat is mitigated by its amenities and proximity to Siena, as well as to such lovely hill towns as Monteriggioni.

If vine-covered pergolas, meandering pathways and Victorian iron furniture with cream umbrellas are your vision of paradise, then the spa-retreat Borgo Santo Pietro is a must visit. Overlooking the lush Valle Serena, near the Abbey of San Galgano (where the sword of the eponymous saint still rests in the stone into which, according to legend, he plunged it), the 13th-century stone villa instills in guests a tranquil well-being with its exquisite traditional Italian rose gardens, organic cuisine, medicinal herb plantings and spa treatments utilizing products from Borgo's garden. An intoxicating perfume infuses the entire property, while birdsong, multiple cushioned seats and an infinity eco-pool induce serene relaxation. Undeniably romantic—soft music plays throughout the nine-bedroom villa (there are seven additional garden suites), and wood fires blaze in the deep stone fireplaces, even in August—Borgo Santo Pietro is the ideal location for small weddings.

Guestrooms vary in size and décor, but all provide delicious goose-down duvets, handmade mattresses and soothing lavender incense oil. The Valle Serena room, which has the best view, features a pleasing turquoise and pale-gold palette, while the only ground-floor suite, Rinaldo Pievano di Sorciano, is outfitted with a crystal chandelier, french doors, a freestanding tub behind a Victorian screen and an antique rare black marble fireplace in which a fire can be lit upon request.

Meals are taken seriously at Borgo’s Saporium (formerly Meo Modo). Dinner is especially atmospheric, served either on the loggia, providing views of the valley through ivy-covered columns, or in the intimate dining room, whose hand-painted walls, silk-brocade curtains and flickering candelabra (the Borgo goes through 30,000 candles a season) inspire love sonnets. There’s an impressive wine list and if the cuisine invites overindulgence, a walk along the fragrant lanes of the extensive gardens provides just the remedy.

The 12th-century Castello del Nero greets visitors with austere graciousness. The spacious terracotta foyer recalls those of grand hotels, while the expansive back terrace presents a Tuscan panorama complete with cypress trees and rolling hills clothed in shades of green and yellow stretching to the horizon. Matching its surroundings in splendor, the hotel’s COMO Shambhala Retreat spa offers holistic treatments alongside signature spa essentials. Non-spa guests will appreciate the urban-hotel-style amenities, like the large fitness area, 24-hour room-service and ample executive suites, whose marble bathrooms feature free-standing claw-foot bathtubs and tiled rain showers.

The hotel is 30 minutes from Florence by the complimentary, twice-daily shuttle and equally close to Siena and the Chianti region, accessible by car. During the summer months, guests can dine on the romantic terrace. With the luxury and amenities of a metropolitan hotel, plus faultless service and a supreme Tuscan location, Castello del Nero will turn even the most diehard urbanites into country mice.

The 18th-century Villa Riccuci, located within the Castello di Ama borgo, accommodates guests in three gracious suites decorated with traditional furnishings and offering panoramic views of the Tuscan countryside. The San Lorenzo suite on the ground floor includes a modern lounge room; L'Apparita with a second bedroom is best for families; and Bellavista, on the second floor, is a favorite with two bedrooms, a picture window and an adjacent communal sitting area that doubles as a bar.

Guests are invited to take a private tour of the 200-acre vineyard, which includes on-site wine-making facilities, the olive oil production plant and the spectacular contemporary art collection that is sprinkled throughout the grounds. The excellent restaurant, Ristoro di Ama, serves guests and visitors three meals a day, and wine tastings are available at L'Enoteca.

The castle portion of Castello di Velona dates from 1000 AD and the grounds were the setting for battles between the 12^th-century militaries of Siena and Florence. During the Renaissance period, the property was transformed into a residential villa and later into a hotel.

Forty-six rooms are divided between the historic castle's main building and the new, modernized area in the spa wing. Suites in the castle are more traditional and tend to be somewhat dated in style, while spa wing rooms are smaller, more modern and colorful, with bright red and yellow furniture and beautiful marble bathrooms with bathtubs that can fill with water directly from the hot springs.

The four pool areas and spa are a highlight of Castello di Velona as many feature restorative hot spring waters. Spa treatments are excellent and there is a full snack bar offering drinks and lunch by the pool—a rarity in Tuscany.

Hidden among the fragrant bushes of rosemary and lavender, this hotel is technically located in Maremma, but is an easy driving distance to Florence, Chianti and Porto Ercole. Castello di Vicarello is every bit the enchanted castle in the hills, overlooking the valleys of Maremma and, on a clear day, all the way to the shimmering line of the sea. Carlo and Aurora Baccheschi Berti, who is known for her Italian cookbooks, spent 11 years renovating this castle into their family home. The castle’s original stone walls and interior pebble-and-grass courtyard hail from the 12th-century, while interiors are adorned with various global treasures from the family's travels.

Now managed by Carlo and Aurora’s sons, Neri and Brando, the property has added a larger farm-to-table culinary program, and activities like cooking classes, horseback riding, wine tastings at the on-site vineyard and harvesting olives in the fall. For those seeking relaxation, there are multiple walking trails and two outdoor pools. While there is no standalone spa, the hotel offers a romantic Spa Suite featuring a sauna, a steam room and an outdoor jacuzzi overlooking the beautiful Tuscan countryside.

There are seven unique suites that mix elements like wooden beams and vaulted ceilings with Balinese daybeds, wicker chairs and bamboo dividers curated by Aurora on her travels in Indonesia. The two separate cottages situated within the hillside below offer more space for families.

The dining experience is a true highlight of the property, featuring seasonal menus with ingredients sourced from the property's garden. Meals are communally served in a vine-covered glass atrium with views of the rolling hills, and the homey, warm decor invokes coziness and familiarity.

The intimate Conti di San Bonifacio has only seven bedrooms, allowing guests to really get to know the staff and other visitors. The three bedrooms in the main house and four suites in a separate building (with views overlooking vineyards or olive groves) are simple, chic and thoughtfully designed with rustic elegance. Due to the small size of the property, there are no in-room phones and some accommodations are more compact than others, so splurge on a nicer room if lounge space is a priority.

The beautiful pool and deck offer the perfect place to enjoy a glass of wine and take in the views of the surrounding mountains and vineyards. The main living space is gorgeous, full of white upholstered furniture with accents of leather and animal prints. Chestnut beams adorn the ceilings and terracotta tiles line the floors.

The resort is located in Maremma, a little over two hours from Florence and only 15 minutes from the coast, which is convenient for those looking to add a boat day to their itinerary. If traveling with a small group, consider renting out the entire property (even if you’re not using all 7 rooms) for the ultimate Tuscan experience.

Less than a two-hour drive from Florence, the Tuscan hamlet of Fighine has been a labor of love since Joy and Max Ulfane first purchased the castle estate more than a decade ago. Lovingly restored, the property is now an incredible spot from which to explore this scenic southeastern corner of Tuscany, including the nearby towns of Montepulciano and Orvieto.

Writes Indagare member Thomas Harte, who visited Fighine when it first opened in 2012: “Fighine is surrounded by wooded countryside and well-tended olive groves, accessed by gravel roads from the nearest towns. You enter the village through an arched gate connected to the castle on a one-loop road. There are about 15 buildings in total, including the five rentable villas, houses for the staff and long-term residents, a clubhouse and restaurant, a hall and a small church, which seems to have both new and restored frescoes. The castle itself dates to the 11th-century.

“Ristorante di Fighine deserves a special mention. In the summer, there is an outdoor garden for alfresco dining. The beauty of Fighine is its remoteness and solitude, which could also be the downside for some. It was ideal for my wife and me, but may seem a bit too remote for others (and driving up the hill’s switchbacks can be a challenge). We both felt it would be a lot of fun to go back with friends and rent a few of the houses to get the best out of this extraordinary place. What the Ulfane family has done is not only remarkable—it is important.”

The salmon-pink Fontelunga villa sits majestically on a hill overlooking sweeping views of the Val di Chiano and surrounded by rambling, pale purple wisteria. Owned and managed by an English/Italian couple, the property is casual, comfortable and welcoming—and the kind of place where walking around barefoot and flopping down on a sofa with a book is encouraged—and the owner's dogs will probably hop up and join you.

The main house has nine bedrooms, a tennis court, pool and Jacuzzi and is outfitted with brightly hued decorations with Art Deco influences (some outlandish, all very vibrant).

The hotel acts more as a bed and breakfast than a full-service hotel, but the owner is delightful, knowledgeable and eager to help with arrangements and recommendations. The property can schedule on-site cooking lessons, dinner parties, touring and transfers, but most guests tend to enjoy their time by the pool, in the Moroccan-inspired lounge area and the gravel al fresco dining area, relying on their own devices for exploration around the area. Cortona is nearby and Siena is a 45-minute drive away, plus the area is famous for being home to Italian brand outlets like Prada, Gucci and Ferragamo.

There are two nearby stand-alone villas for those looking for privacy. The two-bedroom Villa Gallo has its own kitchen and one-bedroom Villa Galletto boasts a private deck and garden. The two villas share their own pool separate from the main property.

Located within the popular oenophile destination of the award-winning medieval Castello Banfi, near Montalcino, the 14-room Borgo still manages to provide a surprising level of serenity. The property, which opened in 2007, features an elegant, terraced pool, separate stone-cottage suites, some of which come with such details as brick arches, and sweeping vineyard views.

The Borgo’s most appealing asset, however, may very well be its proximity to the winery and Taverna restaurant, with its multi-course wine-paired menus. Guests can swill and sample many vintages without concern, knowing they don’t need to drive back to the Borgo’s guestrooms. Instead, they can stroll back to the accommodations, which come with large plush beds and modern bathrooms with ceramic-tiled glass showers.

A resort hotel set in a medieval Tuscan village is not a new idea, but Il Borro, located in the northeast corner of the region, is perhaps the most successful example. It is owned by the Ferragamo family, whose love of the 700-acre place is evident in every detail. Old meets new in a spectacular marriage, with a minimalist contemporary spa sitting in a centuries-old building and a chic, airy bistro overlooking the village. (Parts of the property in fact date back to ancient Roman times.)

Twenty-five suites are situated in homes lining a small corso amid the town’s chapel, shoe store and jeweler. There are also guest rooms in a stunning, cotton candy–colored villa, which boasts an indoor pool, a billiards room and a gym. On one of our recent visits there, Tom Hanks was checking in to the villa’s highly sought-after Royal Suite, which features custom-made wallpaper by Ralph Lauren (a friend of the Ferragamos). The family’s current patriarch, Ferruccio, the son of Salvatore (founder of the famed fashion label) escapes to Il Borro from Florence on weekends, staying in his large white house on the resort’s grounds; you’ll know he’s there if the green shutters are open.

The property sits at the edge of the Upper Valdarno basin (Il Borro translates to "the gully"), and there are dramatic views and meandering pathways throughout the grounds. A particularly beautiful setting is visible from the resort's two main restaurants, Osteria del Borro and the more casual Tuscan Bistro.

There is a beautiful, modern spa, yoga and fitness classes, an outdoor pool (and indoor one for the use of those staying in the main villa) as well as activities available that range from tennis and golf to vineyards visits, hiking and horseback-riding.

La Bandita, the brainchild of former New York City music executive John Voightmann, is a lovingly restored farmhouse perched on a hilltop offering panoramic views over the Val d’Orcia, a UNESCO World Heritage landscape. The property consists of a five-bedroom main building and “Pig Sty” annex, a suite perfect forsmall families or couples seeking privacy. The interiors of La Bandita have been stripped down and renovated in a calming minimalist style with sleek modern fixtures. White rooms are brightened by splashes of color and feature custom-built platform beds, white chaise longues and in-room bathtubs; bathrooms are equipped with luxury toiletries and giant open-air rainfall showers.

Be aware that the road leading to La Bandita is an unmarked, unpaved dirt road. Due to this infamous drive, most guests choose to stay put, lounging by the infinity-edge pool and taking in the property’s stunning vistas. Gourmet meals are prepared by the on-call chef, and are served en famille so guests feel like they are among friends in a stylish country home. Guests report that lunch and dinner on-site were deliciously prepared with the freshest ingredients, and they enjoyed meeting the other guests, many of them fascinating travelers from around the world.

If you do want to explore, you can visit the charming hamlet of Pienza; take a day trip to Montepulciano or arrange a vineyard visit.

Former New York City music executive John Voigtmann and his travel writer wife Ondine Cohane opened La Bandita Townhouse in 2013 as a sister property to their countryhouse hotel, La Bandita. Set in a 15^th-century convent, the boutique hotel maintains its historic exterior and many details, including religious icon niches and rough-hewn stone walls.

The 12 bedrooms are contemporary in style, with funky modern furniture, (like yellow lacquer trapezoidal desks), exposed stone walls, high ceilings, pale hardwood floors and large windows. Stainless steel, four-poster bed frames anchor the rooms and are made with crisp white linens bordered with orange stripes. Bathrooms are spacious and include state-of-the-art fixtures and amenities from Sicilian brand Ortigia.

While the bedrooms are sleek and sexy at La Bandita Townhouse, the common spaces are more laid-back and lounge-like. The large open library has deep upholstered couches, an honor bar and a wall filled with records (and a record player guests are encouraged to use) as well as well-thumbed paperbacks and travel guide books.

The hotel restaurant, Townhouse Caffé has an open kitchen with bar seating that encourages guests to watch the chefs at work, turning out carbonara-filled ravioli (a must-order), bistecca fiorentina and seasonal specialties, like grilled asparagus with soft boiled egg and truffles in spring. More seating is available in the serene back garden.

The hotel's location, however, is its best quality, being set in the center of Pienza, one of Tuscany's most adorable medieval villages. Designed by Pope Pius II, who was born there, the town is the Renaissance ideal, with city walls, parallel streets, a purpose-built cathedral and of course, an adjacent, grand papal summer residence.

The opportunity to sleep within the walls of a medieval Tuscan village (and in high luxury) is notably absent in the region, with this as its one exception. When day-trippers depart as the sun starts to set, the town empties and guests of La Bandita Townhouse have Pienza to themselves, it feels magical.

The harbor-side boutique hotel La Roqqa delivers classic Italian design glamour and a home base for exploring Tuscany’s coast.

Tucked between vineyards and farmland—yet just a stone’s throw from Siena and Sinalunga—Locanda dell’Amorosa offers a historically rich and verdant haven. The 12th-century inn, which survived World War II bombings, has been owned by just two families. It comprises a frescoed villa, a consecrated church with its own parish priest, various stone cottages and guestrooms refashioned from former laborers’ quarters. The garden swimming pool, with its a rose-covered pergola, merits special mention for its elegant setting amid cypresses and olive trees.

The 27 rooms vary in size and style depending on their location. If you prefer something a bit more modern, request a room in the villa (number 32 has a nice, spacious bathroom); for typical Tuscan country details like brick arches, fireplaces and beamed ceilings, choose room number 45 on the second floor of the loggia area.

Locanda has two restaurants: the casual Osteria is ideal for a light lunch or afternoon wine with fresh pecorino. Le Coccole dell’Amorosa, in an elegant stone-walled dining room remodeled from the original stables, offers candelit tables and a 200-bottle wine list. There is a flower-lined terrace that is open during the warmer months, and a wood-burning fireplace for cooler weather. Private dinners in the ancient wine cellars are also available upon request. Travelers should know that with only a portion of the property fully restored, Amorosa remains a work in progress.

There is a serious dearth of contemporary, well-designed (and not exorbitantly priced) hotels along the Tuscan Coast, but even with that lack of competition, this spot, opened in 2010, created a new standard. The 12 rooms (ranging from standard-sized doubles to spacious suites), plus four apartments in a separate farmhouse, look onto 50 acres of vineyards and the sea in the distance.

One of the best aspects of the resort is its sense of space, with plenty of shaded areas, a large living room with a fireplace, a huge pool, and even a playground for the little ones in tow. (Many of the seaside hotels don’t even accept kids under 12, so the touches like a playground and friendly staff is particularly welcome). There is a nice restaurant that serves a small but local menu, and a tiny spa available for treatments booked in advance. Chic but understated, the rooms offer comfy beds with butter soft linens, Allegra Hicks–designed pillowcases, contemporary art, and coffee-table books on the area. It feels very much like its own retreat even though it’s still close to the charming town of Capalbio.

Don’t miss restaurant Il Frantoio and the tarot garden, Il Giardino dei Tarocchi, with its 22 sculptures by French-born artist Niki de Saint Phalle. Fabulous beach clubs like Vino e Rosso and Ultima Spiaggia (with their excellent restaurants and daybeds available for rent) are only a short drive away too. We recommend renting a car to drive to the sea or surrounding towns; there is a shuttle, but it is preferable to have your own wheels.

At 2,600 feet above sea level, Monteverdi seemingly overlooks all of the UNESCO-protected Val d’Orcia. With 12 rooms and three villas, the hotel occupies nearly three quarters of the sleepy town of Castiglioncello del Trinoro, allowing guests of the hotel to experience life in small-town Tuscany.

Navigating the hilly property can be a challenge (even by car), so once there, most guests stay on-property. For those who enjoy exploring, however, Monteverdi is well situated for day trips to explore the less touristy towns of Tuscany. Michael Fioci, the property’s owner, has created a fantastic guidebook that can be found in each room and details his insider knowledge of the surrounding towns and villages.

All the accommodations at Monteverdi are modern, while still retaining traditional Tuscan elements. The room décor is simple yet rustic in neutral hues. Ceilings have exposed beams, walls are constructed of thick stone and the chic interiors are light and breezy. Some of the bathrooms offer little privacy, so be sure to request a room with a separated bathroom. The three- and six-bedroom villas are very spacious and cozy, and come with amenities like a full kitchen, private wine cellar and private outdoor pergola.

Days at Monteverdi can be spent relaxing in the gardens, sampling local wines, swimming in the small pool or using the gym to prepare oneself for that night’s feast. The hotel also has a cooking school with a state-of-the-art teaching kitchen. The fine dining restaurant, Oreade, is a local favorite as the neighbors can attest. Should one wish to venture into the surrounding region, a number of excursions are available, including art tours, olive oil tastings and hot-air balloon tours.

Indagare Tip: The drive to Monteverdi is bumpy and tricky to navigate, so we recommend arranging a car and driver for your arrival and to get specific directions when exploring on your own.

With just six rooms, plus a four-bedroom villa, this Tuscan hideaway opened last year and is just 45 minutes from both Florence and Siena. It’s a top pick for food lovers, as the restaurant, Il Sorbo 1384, is a big draw. Tip: The amazing GM, Andrea Pieri, makes a wonderful Negroni.

This 11-room hideaway is perfectly positioned between spectacular waterfront villages like Popolunia and Bolgheri, as well as a number of the additional hidden gems along the Tuscan coast. Its own wonderful destination restaurant, Il Sale, and its garden-surrounded pool make it a tempting spot for just staying put.

The 11 suites are divided between the early-20th-century main house and a series of buildings in the landscaped gardens. All have enormous bathrooms with double sinks and walk-in showers, and several come with sea views or their own secluded private outdoor area. If you can, splurge for one of the Royal Suites, which claim spectacular vantage over both the sea and the village of San Vincenzo.

One of the biggest draws here is restaurant Il Sale: a seasonal- and local-focused spot with excellent seafood, grass-raised Chianina beef and plenty of veggie options on a spectacular terrace. Wines from the local estates are excellent too.

When Siena House’s British owners, husband and wife Malvin and Amanda, first came to Tuscany, they designed their villa as a family home, but along the way they decided to open the stylish escape to friends and paying guests too. The four-room villa features a mixture of coziness and style, which makes it the perfect choice for people looking for a boutique-chic stay with real intimacy.

Rooms are quite large for the price, with freestanding bathtubs by designers Matteo Thun and Philippe Starck, king-size beds with luxurious Frette linens, and sweeping views of the valley of the Val di Chiana, and the Apennines in the distance. In the public spaces, a large open kitchen showcases local jams and spices (from the gorgeous fragrant gardens), and the small reception is lined with lovely paintings by Amanda. Guests will find evidence of the couple's playfulness throughout the villa—from the vintage pinball machines by the bar, slowly turning blue-painted fans in the kitchen, and the large screen that pulls down for movie nights in the living room upstairs. A final bonus: The large saltwater pool that looks out onto the surrounding farmland.

This isn't a conventional hotel—as the owners admit on their website, “We wouldn’t have a clue how to run a hotel"—but it's all the better for it. You may not find yourself cosseted with the typical full-service amenities; for example, only breakfast is served but guests are able to use the kitchen to prepare other meals or, better yet, go to one of the many great options in the area. And what you do get is the kind of setting that you might find at a stylish friend’s home, plus the sort of insider recommendations of where to eat and what to see nearby that can only be culled from years of experience in the area.

The location in the Val di Chiana might not be as picturesque as that of neighboring Val d’Orcia, but Siena House's proximity to both the A1 highway and the wine capital of Montepulciano make it seriously convenient.

Situated on more than 2,700 acres of vineyards, olive groves, woods and lakes, Toscana Resort Castelfalfi is an 800-year old medieval hamlet that has been given new life. Once a rural Tuscan hilltop village, it was nearly deserted by the time its restoration project began in 2007. Now the property boasts modern and restored apartments, a hotel and leisure facilities that preserve the town’s original beauty while also reviving its soul and reputation as a world-class destination.

The ancient borgo (village) has 48 completely renovated apartments as well as several casali (country villas), some of which have private gardens, pools or verandas (certain villas and apartments are available for purchase and/or rent). At the heart of the borgo lies the castle, which features a bar, cooking school and panoramic terrace overlooking the countryside. Historic buildings house several elegant apartments featuring natural stone, terracotta or oak flooring and travertine marble, glass and rain-showers in the bathrooms.

With 27 holes and more than 10,280 yards of hillside greens, the golf course, which ranks second best in Italy, is not to be ignored. Swimming, massages and spa treatments are also available at Le Piscine, a complex that has four swimming pools, a gym, two saunas and a wellness and beauty area. Both relaxed and upscale dining options are available at Castelfafi—two restaurants (Trattoria Il Rosmarino and La Rocca di Castelfafi) offer seasonal, traditional dishes highlighting simplicity. The village also houses new boutiques offering products from the region, including olive oil, wine, furniture and jewelry.

Consisting of 12 guests rooms, including four suites, Villa Sassolini is designed in shades of grays and browns with dim lighting and comfortable, elegant furniture and sitting areas.

Service here feels more like a bed and breakfast than a hotel, but there is all-day dining offered both alfresco and in the small restaurant. The spa has a sauna and Turkish bath and there is a diminutive but lovely outdoor pool with lounge chairs.

The hotel also offers cooking lessons and has bikes available for guests who would like to explore the region.