Florence’s grandeur is undeniable, but just beyond the city walls you’ll find another kind of beauty—rolling vineyards, olive groves, and medieval villages that embody the soul of Tuscany. If you’re seeking a stay that balances easy access to the city with the idyllic romance of the countryside, the villas, estates, and castles that dot the Florentine hills offer an unparalleled escape.
These historic retreats, often set in centuries-old farmhouses or noble residences, combine the rustic charm of Tuscany with today’s impeccable luxury. Whether you’re sipping Chianti at a vineyard estate, unwinding in a Renaissance villa, or indulging in a spa experience inside a medieval castle, these are the hotels that offer the perfect way to experience Tuscany just beyond Florence.
Editor’s note: most of the hotels below are available seasonally, from April to October.
FH55 Hotel Villa Fiesole
Location: Fiesole (Florence Hills)Driving time from Florence: 20 minutes
Set in the hills of Fiesole, this 19th-century villa offers sweeping views of Florence’s skyline. Guests can relax by the pool, surrounded by lush gardens, or dine on the terrace of the MICHELIN-Starred restaurant overlooking the city. With its blend of historic architecture and contemporary touches, Villa Fiesole strikes an ideal balance between country retreat and city convenience—and it’s located only 5 miles from the heart of Florence. The villa's 32 spacious rooms feature frescoed ceilings, wood flooring, and classic Italian furniture, along with plenty of modern amenities.
Villa il Poggiale
Location: San Casciano in Val di Pesa (Chianti)Driving time from Florence: 25 minutes
Just south of Florence, Villa Il Poggiale is a 14th-century gem that radiates old-world Tuscan romance. Its 24 uniquely designed rooms feature antique furnishings, frescoed ceilings, and textiles from local artisans. Soft, earthy tones made from natural pigments give each space an authentic Tuscan feel. Surrounded by jasmine and hydrangea gardens, the outdoor pool is the perfect place to unwind, while the spa offers treatments infused with the natural bounty of the region, including grapes, olives, and essential oils. Dining is hyper-local and seasonal, with ingredients sourced from organic farms and a curated selection of Tuscan wines from both renowned labels and yet to be discovered nearby producers.
Book Villa Il Poggiale with The MICHELIN Guide →
Salvadonica
Location: San Casciano in Val di Pesa (Chianti)Driving time from Florence: 30 minutes
A family-run agriturismo in the heart of Chianti, just outside San Casciano in Val di Pesa, Salvadonica offers a relaxed and luxurious Tuscan experience. Stay in one of 30 contemporary rooms featuring exposed wooden beam ceilings and frescoed walls—make sure to sign up for activities like horseback riding, tennis lessons or daily tasting sessions showcasing the estate’s own wine and olive oil. Don’t miss dining at La Volpenera, the on-site restaurant, where you can savor regional home-cooked delicacies.
Book Salvadonica with The MICHELIN Guide →
COMO Castello del Nero
Location: Barberino Tavarnelle (Chianti)Driving time from Florence: 30 minutes
This 12th-century castle is one of Tuscany’s most exclusive retreats, earning it One MICHELIN Key in 2024. With interiors by Paola Navone, COMO Castello del Nero perfectly blends historic charm with contemporary elegance. The 50 rooms and suites are effortlessly stylish, featuring cool-toned decor with original 18th-century frescoes. For an extra-private escape, you could also stay at a secluded five-bedroom villa from the 1700s, complete with its own pool and breathtaking countryside views.
Unwind at the COMO Shambhala spa, take a yoga class by the outdoor pool, or wander through 740 acres of beautifully manicured gardens and vineyards. Dining is just as spectacular, with the MICHELIN-Starred La Torre offering unforgettable farm-to-table gastronomy.
Book COMO Castello del Nero with The MICHELIN Guide →
Tenuta Le Tre Virtù
Location: Scarperia e San Piero (Mugello)Driving time from Florence: 40 minutes
Tucked in the lush Mugello countryside, Tenuta offers a dreamy stay in a restored 17th-century stone farmhouse. Surrounded by the Apennine mountains and rolling green valleys, it’s the perfect base for outdoor adventures—plus, one of Tuscany’s top golf courses, Poggio dei Medici, is just a short drive away.
With only seven rooms, the atmosphere is intimate and exclusive. Exposed beams, hand-decorated ceramics, and Tuscan wrought iron blend rustic charm with understated elegance. Each room is painted a unique color and paired with a matching scent: fresh-cut wildflowers, lavender, or citrus. No TVs here, just shelves full of books for the ultimate unplugged retreat.
While there’s no on-site restaurant, you do get to enjoy a daily breakfast; and a private chef service is available on request. Spring 2025 marks the launch of Tenuta’s first organic wine, Ventitré, a limited-edition blend of cabernet franc, cabernet sauvignon, and merlot—best enjoyed while relaxing poolside.
Castello La Leccia
Location: Castellina in Chianti (Chianti)Driving time from Florence: 40 minutes
Perched on a Tuscan hilltop with views stretching to San Gimignano and Siena, Castello La Leccia is a beautifully restored 11th-century estate. Centuries of history are woven into every corner—from its medieval fortress origins to its loving restoration by the Sonderegger family. More than just a luxury retreat, it’s a family-run passion project—an organic farm, a wine estate, and a place where simple things are done exceptionally well.
The 12-room stone manor house is understated yet refined, with exposed beams, sleek interiors, and a deep connection to its past. The infinity pool and pergola-shaded terrace offer breathtaking views, while the on-site spa, yoga classes, and guided wine tours invite relaxation and exploration. Castello La Leccia’s "km zero" restaurant serves fresh, hyper-local Tuscan cuisine, paired with wines from its own organic vineyard.
Book Castello La Leccia with The MICHELIN Guide →
Viesca Toscana
Location: Reggello (Valdarno)Driving time from Florence: 40 minutes
Once the beloved summer retreat of the Ferragamo family, Viesca Toscana is now an elegant countryside escape just over 20 miles from Florence. Set on 173 acres of rolling Tuscan hills, this luxury estate offers everything from 16th-century villas with private pools to charming suites tucked into a quiet borgo. It’s the kind of place where luxury service meets the laid-back comfort of a private home—think infinity pools, in-villa chefs, yoga under the cypress trees, and bikes to explore the scenic trails.
At the heart of it all is Il Borro—part restaurant, part bar, part gourmet shop—where Executive Chef Andrea Campani serves up farm-to-table dishes using local, organic ingredients. Guests can also join cooking classes, unwind at the spa, or sample wines from Il Borro’s own vineyards. Whether it’s horseback riding, tennis, or simply soaking in the views with a glass of wine, Viesca Toscana is a slice of Tuscan life that's nearly impossible to leave.
Book Viesca Toscana with The MICHELIN Guide →
Pieve Aldina
Location: Radda in Chianti (Chianti)Driving time from Florence: 1 hour
Once a medieval hamlet, Pieve Aldina has been transformed into a tranquil Tuscan sanctuary only 50 minutes away from Florence. Perched on a hill in Chianti, this estate is surrounded by vineyards and centuries-old cypress trees—the perfect hideaway for wine lovers and history buffs. The beautifully restored stone buildings house elegantly understated rooms, while the on-site restaurant, which opens out into the gardens, highlights local ingredients. When you’re not getting pampered at the spa or using the outdoor swimming pool, you’ll be tempted by the range of available onsite activities, from picnics and yoga classes in the vineyards to weekly Tuscan barbecues under the olive trees.
Book Pieve Aldina with The MICHELIN Guide →
Castello Di Spaltenna
Location: Gaiole in Chianti (Chianti)Driving time from Florence: 1 hour
Nestled among rolling Tuscan hills and endless Sangiovese vineyards, Castello Di Spaltenna is a 1,000-year-old monastery turned luxury retreat. With just 37 rooms spread over three floors, each space is unique—think four-poster beds, 18th-century writing desks, classic fireplaces, and Jacuzzis for two. Sunbathe near the serene outdoor pool or relax in the brand-new indoor heated pool and whirlpool area. Whether inside or out, the surroundings are pure magic, framed by cypresses, olive trees, and wild woodlands.
The estate is also home to three restaurants, including the MICHELIN-Starred Il Pievano, soon to be helmed by acclaimed Chef Antonio Iacoviello.
Book Castello Di Spaltenna with The MICHELIN Guide →
Borgo Pignano
Location: Pignano (Volterra)Driving time from Florence: 1 hour
Nestled in the hills near Volterra, Borgo Pignano is a dreamy escape where sustainability meets creativity. This organic farm estate is all about homegrown luxury—it produces its own honey, beer, olive oil, wine, and even the bathroom amenities, while its onsite restaurant was awarded a MICHELIN Green Star for its zero-mile philosophy. Here you can dive into a range of exclusive, thoughtfully curated experiences, from forest bathing and organic cosmetics workshops to horseback riding and truffle hunting. At the end of a long day, unwind in an infinity pool carved from a limestone quarry.
The rooms exude charm, filled with antique furnishings and organic textiles that make the space feel effortlessly warm and inviting. If you’re traveling with a group, the estate’s eight newly-launched villas offer plenty of space, each with its own private heated pool and a dedicated electric buggy to zip around in style.
Book Borgo Pignano with The MICHELIN Guide →
La Collegiata
Location: San Gimignano (Val d’Elsa)Driving time from Florence: 1 hour
Set in a serene, 16th-century monastery, La Collegiata feels like stepping into a quieter, simpler time. With just 20 rooms, this charming boutique hotel offers a peaceful retreat, complete with a lovely outdoor pool, lush gardens, and a cozy bar area. The rooms are decorated in classic Tuscan style, featuring warm hues of ocher, green, and burgundy, with touches of blue. You’ll also find all the modern comforts you need, from air conditioning to contemporary bathrooms to Wi-Fi.
Dining here is an experience in itself. The former monastery chapel has been transformed into the stunning L’Eco Divino restaurant, where you can enjoy local, seasonal dishes paired with wines from the well-stocked cellar. Surrounded by gardens, it’s the perfect spot to dine al fresco, with views of the iconic towers of San Gimignano in the distance.
Book La Collegiata with The MICHELIN Guide →
Villa Sassolini Country Boutique
Location: Moncioni, Montevarchi (Valdarno)Driving time from Florence: 1 hour
With just 10 uniquely designed suites—ranging from sleek monochrome minimalism to opulent Tuscan grandeur—Villa Sassolini is an intimate retreat offering stunning views of the Chianti hills and charming village streets. This secluded hideaway in Moncioni blends impeccable design with a passion for gastronomy. Its restaurant, led by a celebrated chef, offers a contemporary twist on Tuscan cuisine, while the tranquil swimming pool overlooks the rolling countryside, creating the perfect setting for a stylish and relaxed escape.
Book Villa Sassolini Country Boutique with The MICHELIN Guide →
Hotel Borgo San Felice
Location: Castelnuovo Berardenga (Chianti)Driving time from Florence: 1 hour and 15 minutes
Borgo San Felice isn’t just a top hotel—it’s an entire medieval village brought back to life, with cobblestone streets, centuries-old buildings, and serious storybook charm. Tucked in the heart of Chianti, it’s home to a MICHELIN-Starred restaurant, top-notch winery, dreamy spa, and even its own little chapel. Start your day with breakfast on the sun-drenched terrace of your Tuscan-style suite, or go big and rent a rustic villa with 18 of your closest friends. You’ll be feasting on veggies and olive oil straight from the estate’s gardens and sipping Chianti made from the vines just outside your door. It’s the kind of place that makes you want to slow down, soak it all in, and maybe never leave.
Book Hotel Borgo San Felice with The MICHELIN Guide →
The Fontanelle Estate: Le Fontanelle and The Club House
Location: Pianella (Castelnuovo Berardenga, Chianti)Driving time from Florence: 1 hour 25 minutes
With two countryside hotels to choose from, this elegant estate is a dream for golfers, spa lovers, and anyone seeking pure relaxation. The adults-only Club House features MICHELIN-Starred dining, an 18-hole golf course, a stunning outdoor pool with panoramic views, and one of Italy’s top holistic spas. Meanwhile, Hotel Le Fontanelle, set in a 13th-century farmhouse, charms with terraced lawns, terra-cotta patios with sweeping views of the Chianti valley and outdoor dining under the summer stars.
Both properties blend Tuscan tradition with modern sophistication, offering a refined yet cozy home away from home vibe and a choice between three restaurants and two bars across the estate. If you’re a wine lover, Fontenelle's own Vallepicciola winery—under the same family ownership—is yet another on-site treat waiting to be explored.
Book Le Fontanelle or the Club House with The MICHELIN Guide →
Hero Image: COMO Castello Del Nero
