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There’s a reason so many artists, poets, writers, chefs, and vintners have been inspired by the Chianti region of Tuscany: It's a feast for the senses, with an incredible gastronomic tradition, fantastic wines, sweeping panoramas, and the smell of cypress wafting through the air. It’s perfect for when you need to escape the grind. The Chianti region is dotted with small villages making up its geography—and some hoteliers are turning decaying, crumbling hamlets into resorts that breathe life back into the townscape while providing guests with the unique experience of staying in a Tuscan village.
With the plethora of gorgeous lodging options in the region, it can be hard to narrow down where to stay, especially when so many properties have scenic outdoor pools, incredible restaurants, and perks like on-site wineries and cooking classes. We’ve done the hard work, curating the perfect list of lodging options in Chianti for every sort of traveler. Read on for our top nine picks, below.
Best Overall: Villa Le Barone
Villa Le Barone, built from a 16th-century manor house, is consistently ranked as one of the best places to stay in the region, and for good reason. The hotel is set back in Chianti’s stunning countryside, and it’s perfect for guests who love wine, food, gardens, and Tuscany’s incredible fresh air. Rooms are charming and live up to the hotel’s feeling of a luxurious country house. They highlight original architectural features, like arched brick ceilings, and all include free WiFi and 24-hour room service.
On the property, you can stroll through the rose garden, take a dip in the pool, do a wine tasting, or try out a cooking class. There's Il Torchio for dinner, which is located in the old wine cellars (with the option to eat outside, weather permitting), serving up the best local flavors and wines. Light lunch and snacks are served on the terrace or by the pool, plus there are two honor bars and an option for afternoon tea or coffee. If you feel like getting off the property, the hotel is located between Siena and Florence, both just a short drive away and perfect for exploring.
Best Budget: B&B Castello di Fonterutoli
Going for about half the price as the luxe resorts that sprawl across the Tuscan countryside, this bed and breakfast brings all the charm and all the gorgeous scenery into one of the best-value vacations in the region. It’s set within a medieval hamlet, with the individually decorated (and all traditionally charming) rooms located across four old houses so guests feel like they’re really living in a Tuscan village. Inside the rooms, terracotta floors and exposed-beam ceilings mix with crisp linens and antiques.
Nearby is the enoteca, where the property holds wine tastings of vintages from its winery, and there’s the Osteria di Fonterutoli Restaurant within close walking distance of any of the rooms. You can also tour the vineyard itself, take cooking classes on site, and spend time hiking and cycling around the countryside. One handy detail: If you’re traveling in a group—say for a wedding or reunion—you can also rent a whole apartment outright.
Best for Families: Castello del Nero
Kids of all ages (including grown-up ones) aren’t going to forget a stay in an actual castle anytime soon, and this 12th-century towered hotel really delivers. Most importantly, there are tons of activities the whole family can enjoy, from truffle hunting to gelato making classes, bike riding, and a heated pool to swim in when it's warm. Babysitting services are available, as well as suites specifically designed for families (baby cots and extra beds can be added to many of them).
You won't want to miss a day of indulgence in the on-site spa, either: Choose from yoga, massages, facials, body scrubs, and more, or try out the ice fountain or sauna. If you can rouse yourself for dinner, there’s both a more informal Tuscan restaurant on site as well as a Michelin-starred restaurant, La Torre, and options to eat outside in the warmer months. If you're looking to stay in and relax, there's also 24-hour room service available.
Located smack in the middle of a 740-acre estate, the hotel offers plenty of options for picturesque hikes around the acreage or walks into town. If you want to get out in style, however, check out one of the hotel’s Vespas or stylish vintage Fiat 500s. There's also complimentary shuttle service to and from Florence and Siena at set times.
Best Boutique: Borgo del Cabreo
If you want a true retreat, the Borgo del Cabreo is the perfect place to escape. The property itself is set among everything you’ve always imagined the unique countryside to be—vineyards, cypresses, rolling landscapes—and provides a wonderful experience where guests can disconnect. The property’s 10 elegant rooms and one refined suite are bright and airy—think luxe farmhouse—with whitewashed exposed-beam ceilings and accent colors that mirror the land and sky.
At the end of a day of visiting local vineyards for tastings, including this hotel’s own cellars, come back to the heated outdoor pool to relax (open seasonally). Guests can also rent a bike for an adventurous way to explore the surrounding countryside. Breakfast, made up of an incredible local spread, is included in the rates.
Best for Romance: Borgo Scopeto Relais
Couples looking for a wedding spot, a honeymoon escape, or just a romantic getaway will fall in love with Borgo Scopeto Relais’ dreamy property. Close to Siena—just a few minutes’ drive—and surrounded by the traditional Tuscan landscape of olive groves and vineyards, this restored 14th-century hamlet has everything you need for a relaxing getaway with your loved one: two swimming pools, wine and olive oil tastings, tennis courts, and a minibar in each room. The 58 rooms themselves are beautifully decorated, with wonderful linens, modern, refined furnishings, and bathrooms in marble and travertine.
For lunch and dinner, you can dine at the romantic on-site restaurant located in the estate's ancient cellar, and a wonderful buffet breakfast comes included with your stay. There’s also a gorgeous wellness center with a jacuzzi, relaxation garden (complete with Tuscan herbs), and hammam. The on-site bike rental is a great way to explore the panoramic countryside—you can even see Siena’s cathedral in the distance.
Best for Foodies: Borgo San Felice
Part of the international luxury group Relais & Châteaux, Borgo San Felice encompasses what used to be a medieval stone village—now fully restored into a gorgeous, 5-star hotel featuring 30 rooms and 30 suites. Perfect for food and wine lovers coming to take in the region’s gastronomy, the beautiful property boasts not one, but two incredible restaurants: an osteria with modern Tuscan menus, as well as a formal Michelin-star restaurant, which has an impressive wine cellar with 500 different wines. Or you can arrange for dining under the stars with your own private waiter. There's also a bar for an afternoon cocktail or snack, which moves poolside in the summer.
For entertainment, tour the vineyard, take a cooking class, or opt for an exclusive itinerary designed to give guests an immersive, customized experience. Additionally, there’s a heated outdoor swimming pool, two tennis courts, a spa, and a gym. Guests wishing to splurge should definitely book the stunning Suite Legnaia, a two-story space tucked back to one side of the estate complete with a romantic soaking tub and private garden.
Best for Luxury: Castello di Spaltenna Exclusive Resort & Spa
If you're looking for a five-star experience with unparalleled scenery and service, the Castello di Spaltenna delivers—from the rooms to the amenities to the food. The property, which features a castle that was originally a 10th-century monastery, has been renovated to combine elements of the modern with the refinement of the old. Guests can relax near the outdoor swimming pool, and in colder months, enjoy the heated indoor pool—one of the only ones in the area. There's an on-site Michelin-starred restaurant, with dishes that complement the local Chianti, as well as a lunch option serving lighter fare in the castle's famed taverns or outside on the terrace. The property’s wine cellar is available for tastings, too.
For the ultimate relaxation, choose a treatment from the spa or try out the Turkish bath. Of course, there are also mountain bikes for exploring, activities like drawing and painting classes, tennis courts, a gym, and a billiard room. When it comes to accommodations, you have your picks of several levels of unique rooms—each featuring a rustic design, WiFi, a TV, and room service—with the most exclusive being the Terrace Suites, which offer a private terrace, incredible views, a separate living area, and a fireplace. All stays also come with a delicious buffet breakfast that you can enjoy while looking out at the majestic scenery.
Best View: Dievole
Not just any Tuscan resort, Dievole is specifically a wine resort, set among the vineyards and olive groves with panoramic views of the Chianti Classico wine area and the Chianti Mountains. The property was an 18th-century estate that now features 28 rooms spread out among five villas, each with an incredible view of either one of the gardens or of the vineyards and valleys. Choose from classic rooms, family apartments, and exclusive suites with their own outdoor living spaces, all of which have WiFi, flat-screen TVs, and include the complimentary breakfast.
Of course, there’s a working winery on site and wine tastings, as well as cooking lessons and excellent restaurants with menus that change monthly, largely focusing on classic Tuscan influences and ingredients (do not miss the award-winning olive oils, either). Get some fresh air by venturing for a walk, cycle, or horseback ride on some of the property’s 17 miles of trails (you can even request a gourmet picnic basket).
Best Agriturismo: Castello di Gabbiano
An agriturismo is a farm stay, a style of vacationing in Italian farm house resorts. However, don't be thrown off by a "farm stay" because Castello di Gabbiano truly delivers on luxury. This restored castle, which dates back to the 12th century, is still a working farm, set back among olive groves and vineyards. All that acreage means guests have plenty of trails to explore, and there’s a wonderful restaurant (open Tuesday evening through Sunday) serving up local specialties. There are also wine tastings each day, as well as olive oil tastings, vineyard tours, and seminars.
If you need something else to do between the food, idyllic wandering, and wine, head to Greve in Chianti (a market town just 15 minutes by car) or stay on site and take a dip in the swimming pool or hot tub. Guestrooms in the castle, with terracotta floors and traditional architecture, are all quite spacious, and antiques mix charmingly with modern furnishings. You can also choose from one of the apartments, well suited for families, with some including their own washing machine. Disconnecting is easy here, too: Keep in mind most of the rooms do not come with a TV, but there is WiFi throughout the castle.