The 9 Best Chianti Hotels of 2019

Villa Le Barone, built from a 16th-century manor house, is consistently ranked as one of the best 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 Tuscan reds, oranges, and greens add gloriously earthy pops of color. On the property, you can stroll through the rose garden, taking in the countryside views, or take in a dinner full of local flavors and Chianti and Super Tuscan wines—you can also do a wine tasting and cooking class on site. If you feel like getting off the property, the hotel is located between Siena and Florence, so there’s two wonderful places a short drive away to explore.

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 them, think terracotta floors and exposed-beam ceilings mixed in with crisp linens and antiques. Nearby is the enoteca, where the property holds wine tastings of vintages from its winery, and there’s also an osteria 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.

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. Uniquely for hotels in Italy, there are plenty of dedicated perks for kids: treasure hunts and other activities, as well as a play area outside. (Parents: There’s also baby essentials and cots available.) Don’t miss a day of indulgence in the on-site spa, either: There’s a heated pool with jets on the veranda, with both mixed-gender and women-only areas inside—expect color-therapy showers, 10 treatment rooms, and saunas and steam rooms. The olive oil massages are a great regional take on the treatment, and teens will love that there’s a facial on the menu just for them, as well as parent-child massages (or, feel free to leave little ones behind—babysitting is available). Back upstairs in one of the 50 guest rooms, interiors are as plush as you might expect, with linens and window treatments that juxtapose well with the government-overseen restoration of the castle interior—and the view out the window is quintessential Tuscany, with cypress trees and villages dotting the background. 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. It’s smack in the middle of a 740-acre estate, within a 15-minute walking distance of the village Tavarnelle Val di Pesa—meaning kids will have plenty of activity to burn up some energy during walks into town and hikes around the acreage. If you want to get out in style, however, check out one of the hotel’s Vespas or stylish vintage Fiat 500s. 

If you want a true Tuscan retreat, the Borgo del Cabreo is the perfect place to escape to. 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, crisp linens, and accent colors that mirror the land and sky (each also has a tea and coffee kettle and air conditioning, a must for a summer visit). 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, which is open from mid-April. Breakfast, made up of an incredible local spread, is included in the rates.

Guests can also rent a bike for an adventurous way to explore the surrounding countryside—just ask the helpful, friendly staff. 

Couples looking for a wedding spot, a honeymoon escape, or just a romantic getaway will fall in love at 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 13th-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. There’s also a gorgeous wellness center with an indoor pool, 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.

This charming, luxurious hotel is a Chianti gem—and it’s perfect for visiting 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-starred restaurant, which has an impressive wine cellar with 500 different wines (or, book dinner under the stars with a private waiter). Head to the spa to continue the wine theme, with treatments that use vino to give you a wine glow of a different sort. On site, there’s a swimming pool, putting green, and tennis court—or, if you’re feeling like a different lunch spot, head to the property’s vegetable garden for a picnic arranged by the hotel. All the rooms are beautiful, with even the baseline rooms beautifully bedecked in traditional Tuscan terracotta and exposed beams. Guests wanting to splash out on their vacation should definitely book the stunning Suite Legnaia, a two-story space tucked back to one side of the estate and complete a romantic soaking tub and private garden.

Ranking among the region’s most luxurious hotels, the Castello di Spaltenna is a five-star hotel that delivers an incredible experience in some of Tuscany’s most beautiful landscapes. And no, we’re not hyperbolizing: The property, built in a 10th-century monastery, has been renovated with Tuscan tastes that combine elements of the modern with the refinement of the old, and views from each soar over the surrounding countryside. Outside, guests can relax near the swimming pool’s waterfall (in the winter, the indoor pool is open). The on-site restaurant is Michelin-starred, with dishes that complement the local Chianti (or eat outside by candlelight)—and be sure to take in a treatment or two at the blissful spa. The property’s wine cellar is wonderful too, so book a treatment or two before your stay. There’s also a billiard room, sauna, Turkish bath, and gym inside; outside, a tennis court and plenty of trails to explore.

A resort sounds nice, but we bet a wine resort sounds even nicer—especially if you’re looking to fully get away from the stress of everyday life. Dievole is one of the top hotels in the area, and it happens to specialize in the vino the region is famous for. The property was an 18th-century estate that looks out over the countryside’s patchworks and ridges, and any view of it is stunning, whether you’re taking it in from one of the resort’s rooms or from one of the two pools, which looks out sans fence onto the landscape beyond. Although everything about a stay here is top-tier, nothing’s overly fussy here: Instead, it’s Tuscan warmth and a quiet elegance. Expect the rooms to be classically luxe: deep tubs, stone floors, and smooth ivories with gold. Of course there’s a working winery on site and wine tastings, as well as cooking lessons and an excellent restaurant that changes menus monthly, largely focusing on classic Tuscan influences and ingredients, as well as adding in proteins from the coast (do not miss the award-winning olive oils, either). Get some fresh air the day after an indulgent tasting with a walk or cycle on some of the property’s 17 miles of trails (you can even request a picnic basket).

If a luxe countryside agritourismo is on the cards, Castello di Gabbiano delivers. This restored castle, which dates back to the 14th century, sets the tone from the start: The property, which is still a working farm, is set back among olive groves and vineyards for a true Tuscan retreat. All that acreage means guests have plenty of trails to explore on site, and there’s a wonderful restaurant (open for lunch and dinner beginning Tuesday evening through Sunday evening) serving up local specialities. Speaking of—oenophiles and foodies, this is your sort of place: There are wine tastings each day, as well as olive oil tastings, vineyard tours, seminars, and honesty bars in two beautiful lounges. If you need something else to do between the food, idyllic wandering, and wine, head to Greve in Chianti (a charming market town 15 minutes by car) or stay on site and dip into the swimming pool or heated hot tub. Rooms are wonderful places to crash at the end of the day too: Guestrooms, with terracotta floors and traditional architecture, are all quite spacious, and antiques mix charmingly with modern furnishings; bathrooms are well-equipped and stocked with Ferragamo toiletries. Disconnecting is almost enforced here—there’s no WiFi in rooms, just in public areas—but this is one place where it’s good to embrace it.