The Ultimate Guide to the Best Places to Stay in Tuscany

Last Updated on October 30, 2025 by Lindsey

Wondering where to stay in Tuscany, Italy? This region is a dream destination if you’re looking to live la dolce vita, but choosing where to stay can feel overwhelming. This guide breaks down the best places to stay in Tuscany, from city hotels to countryside villas.

Tuscany isn’t just about gorgeous villas — it’s one of Italy’s best regions for families. If you’re wondering how to fill your days, our Tuscany with Kids guide covers family-friendly wineries, farm visits, and scenic drives.

Here are our favorite places to stay across Tuscany, from countryside estates to hilltop castles.

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Top Places to Stay in Tuscany

Tuscany offers diverse experiences depending on where you stay. Each area has its charm, from art-filled cities to peaceful countryside retreats. Here’s a breakdown of the best locations for different types of travelers.

Best Tuscan Towns to Stay In

For a mix of history, culture, and food, these towns are excellent choices:

• Florence – Ideal for first-timers and art lovers.
• Siena – A charming medieval city with a rich history.
• Montepulciano – Great for wine lovers.
• San Gimignano – Known for its medieval towers and charm.
• Lucca – Perfect for a relaxed, walkable city.

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Florence: Best for First-Time Visitors & City Lovers

Florence is the best place to stay to enjoy a bigger city experience in Tuscany. The city is full of history, delicious Tuscan cuisine, art, and architecture. The city is also a good base from which to explore the entire region. Stay at Hotel Brunelleschi or The St. Regis Florence.

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Siena: Best for History & Medieval Charm

Siena is an excellent option if you love medieval streets and rich history. The city has a relaxed atmosphere with stunning Gothic architecture. Stay at Grand Hotel Continental Siena for luxury or Palazzo Ravizza for a boutique experience.

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Chianti: Best for Wine Lovers & Countryside Retreats

Booking a hotel in Chianti to enjoy the town’s wine tastings, rolling hills, and local charm. Family wine farms and beautiful farmhouses dot this area. People who enjoy nature and delicious wine will love a Chianti stay. Borgo Scopeto Relais and Castello di Spaltenna offer exceptional countryside stays.

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Val d’Orcia: Best for Scenic Views & Romantic Getaways

Val d’Orcia is one of the most beautiful places to stay in the Tuscan countryside. It’s home to Pienza, Montalcino, and Montepulciano, known for their breathtaking views and charming streets. This area is perfect for couples or families looking for a quiet, picture-perfect escape. Stay at Rosewood Castiglion del Bosco for a five-star countryside experience.

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Lucca: Best for Families & Relaxed Stays

Lucca is great for families. The city is walkable, safe, and filled with charming streets. It has well-preserved city walls that you can bike around, making it a fun and unique activity for visitors.

Stay at Hotel Palazzo Alexander or Palazzo Dipinto for a convenient visit. Or, consider a stay at a luxurious villa such as Il Sogno di Elisa.

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Where to Stay in Southern Tuscany

Southern Tuscany is perfect for a peaceful escape and a slower-paced experience. Visit wine towns like Montepulciano and Montalcino, medieval hilltop towns like Massa Marittima, or cliffside Pitigliano. Stay at Castello Banfi – Il Borgo in Montalcino or the seaside Cala Beach Resort.

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The Tuscan Coast: Best for Beach Lovers

The coast is an excellent option for travelers who want to combine cultural sightseeing with relaxing seaside days. Enjoy a luxurious seaside stay in Forte dei Marmi’s Augustus Hotel & Resort or Viareggio’s Grand Hotel Principe Di Piemonte. Or, go for a relaxed vibe in Castiglione della Pescaia with a rental homes like this one.

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Where to Stay in Tuscany Without a Car

If you don’t want to rent a car, stay in cities with good public transport. These locations have easy access to trains and buses, making it simple to explore nearby towns.

• Florence – Easy access to trains and buses, making it a central hub
• Lucca – Walkable and well-connected, with plenty of attractions nearby
• Siena – A compact, car-free city center that’s ideal for strolling

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Best Hotels in Tuscany for Every Traveler

Tuscany has places to stay for every type of traveler. Whether you’re looking for luxury resorts, boutique hotels, or something unique, here are the best picks.

Best Resorts in Tuscany

Tuscany’s resorts offer a luxurious way to experience the region. These resorts are for you if you seek high-end amenities, spa experiences, and top-tier service.

• Castelfalfi – A golf and spa resort surrounded by olive groves
• Il Borro Relais & Châteaux – A stunning historic estate with beautiful surroundings
• Fonteverde Lifestyle & Thermal Retreat – A perfect spa escape with natural hot springs

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Unique Places to Stay in Tuscany

Want something different? Tuscany has plenty of unique options for a truly memorable experience.

• Monastero di Cortona Hotel & Spa – A converted monastery with elegant rooms
• Sextantio Albergo Diffuso – Stay in a rustic medieval village for an authentic Tuscan experience
• Castello de San Fabiano offers an authentic experience steeped in history. The family-owned castle offered us a warm welcome on our recent visit. Don’t miss their incredible breakfast spread! Though the rooms are more rustic than luxurious, the atmosphere and setting more than made up for it.

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Best Hotels in Tuscany for Families

Families traveling to Tuscany need hotels that offer space, activities, and convenience. These family-friendly hotels provide great options if you’re visiting Tuscany with kids.

• Castelfalfi – A top family resort in Tuscany with pools and golf courses
• Adler Thermae Spa & Relax Resort – A great pick with thermal pools and activities for all ages
• Agriturismo Poggiacolle – A rustic farmstay located near San Gimignano, offering family-friendly amenities such as an infinity pool and rental bikes.

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Where to Stay for a Honeymoon in Tuscany

Looking for the dreamiest hotels for a Tuscany honeymoon? Whether you’re after a romantic vineyard hideaway or a luxury villa with countryside views, options abound in Tuscany. Castello Di Velona Resort offers romance in a 11th century castle. Or, get hands on with a cooking class from a Michelin starred chef at Il Falconiere.

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Places to Stay in the Tuscany Countryside

There’s nothing like waking up to vineyard views and the sound of church bells in the distance. Staying in the countryside means slower mornings, family-run restaurants just down the road, and afternoons spent exploring nearby medieval villages. Choose from agriturismos (working farms where you can stay overnight), historic villas, or luxury estates that blend rustic charm with modern comfort.

Many countryside stays also offer immersive experiences like cooking classes, olive oil tastings, or truffle hunting — perfect for families who want to experience the real Tuscany.

• Villa Campestri Olive Oil Resort – A scenic olive oil estate with tasting experiences
• Belmond Castello di Casole – An elegant retret set in a 10th century castle near Casole d’Elsa.

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Where to Stay for the Best Tuscan Food & Wine Experiences

Tuscany is a paradise for food and wine lovers. These hotels offer world-class dining and wine tastings:

• Relais Il Falconiere & Spa (Cortona) – A luxury hotel with a Michelin-starred restaurant.
• Borgo San Felice (Chianti) – A stunning wine resort with its own vineyard.
• Tenuta Torciano (San Gimignano) – A family-run winery with immersive wine experiences.

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Best Tuscan Villas for Families

Dreaming of your own Tuscan hideaway—rolling hills, infinity pools, and maybe a little vino at sunset? These family-friendly villas deliver the magic of a private stay without giving up the perks of world-class service. From castle-style estates to spa-worthy retreats, here are some of the best Tuscan villas for families.

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Borgo Santo Pietro

If “home” were a 13th-century villa surrounded by lemon trees, this would be it. With just 22 rooms and suites (and most rooms accommodating up to 4 guests) it’s easy for a family to feel comfortable yet exclusive. Families can book elegant rooms or garden suites, each draped in antiques and frescoes. Breakfast happens in a rustic farmhouse kitchen or on a terrace overlooking the hills—a setting that makes even sleepy teens smile. Between the freshwater infinity pool, cooking classes, and endless space to explore, it’s an easy mix of luxury and laid-back Tuscan living.

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Castello di Casole, A Belmond Hotel

This restored 10th-century castle proves that family vacations and five-star style can happily coexist. For families seeking villa-style exclusivity, the private villas on the estate (for example the three-bedroom Villa Thesan) sleep around 6 guests. The property’s private villas feel like storybook homes—think travertine marble baths, outdoor pizza ovens, and gardens perfumed with lavender and myrtle. Guests can wander over to the main hotel for fine dining at Tosca or unwind at the Essere Spa. Kids love the e-bikes and hands-on pizza-making lessons, while adults get their fill of vineyard views and Chianti wines. It’s the perfect balance of relaxation and adventure.

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Villa Ardore

Set high above Chianti’s vineyards, Villa Ardore takes the concept of “family getaway” and elevates it—literally and figuratively. It features eight ensuite bedrooms and accommodates up to about 16-18 guests. This eight-bedroom estate was lovingly restored by a California family, who added all the comforts they wanted for multigenerational travel: a heated infinity pool, a full-service spa, and even a 500-bottle wine cellar for the grown-ups. Interiors are warm and authentic, with reclaimed wood beams, terracotta floors, and cozy fireplaces. Families can fill their days with cycling, pottery, or cooking classes—or simply gather on the terrace with a local wine and that postcard-perfect view of San Gimignano.

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Borgo Pignano

For families craving peace, space, and a touch of storybook beauty, Borgo Pignano delivers. This estate includes eight villas of various sizes and is perfect for a larger family or group of friends booking two or more. Surrounded by olive groves near Volterra, this eco-chic resort offers spacious suites and villas with sweeping valley views. Parents can indulge in the spa or a wine tasting while kids roam free among the fields and gardens. Expect exceptional service, farm-to-table meals, and a sense of calm that makes you want to linger just one more day (or three).

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Villa Il Poggiale

For families dreaming of a classic Tuscan stay without the crowds, Villa Il Poggiale delivers. This 16th-century country residence just outside Florence feels more like a private home than a hotel. Expect frescoed ceilings, cozy sitting rooms, and sweeping hill views framed by olive groves. Parents can sip Chianti on the terrace or unwind by the pool while kids explore the gardens or nearby countryside trails. Warm service, hearty local cuisine, and easy access to both Chianti wine country and Florence make it a perfect balance of serenity and convenience.

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Why Families Love These Villas:
Each offers a perfect blend of privacy and pampering—space for kids to be kids, while parents get the wine-by-sunset moments Tuscany was made for. Whether you’re after the grandeur of a castle or the intimacy of a countryside retreat, these Tuscany villas for families promise unforgettable stays filled with food, fun, and Italian charm.

Many families pair Tuscany with a few days in the Eternal City. Check out our Rome with Kids guide for family-friendly ways to see the Colosseum, Vatican, and beyond. If you’re short on time, you can see the highlights of Rome in just two days.

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Authentic Agriturismos & Farm Stays

If your dream Tuscan getaway includes olive trees instead of infinity pools, an agriturismo might be your perfect match. These working farms give families a taste of real rural life — think sunrise breakfasts with homemade jam, kids meeting resident donkeys, and dinners that start with ingredients grown steps from your table. It’s a slower, more authentic way to experience Tuscany, and still within easy reach of major sights.

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Villa Campestri Olive Oil Resort

For families who love food, nature, and the idea of “slow travel,” Villa Campestri is a standout. This hilltop olive estate in the Mugello Valley is more experience than hotel — complete with tastings, picnics in the groves, and a charming on-site restaurant serving dishes drizzled with their own award-winning olive oil. Parents can relax by the pool or book an olive-oil spa treatment while kids wander the gardens or join a cooking lesson. It’s an easy drive from Florence, but feels a world away.

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Agriturismo Diacceroni

For families seeking wide-open space, rustic charm, and non-stop nature for the kids, Agriturismo Diacceroni delivers. This sprawling farm estate near Volterra features apartments and villas surrounded by olive groves, a playground, horse stables, cooking classes, and even truffle‐hunting adventures. The kids can roam freely while the grownups relax with a glass of local wine at the outdoor table. Comfortable, kid-friendly, and authentically Tuscan.

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Al Gelso Bianco

Nestled in the heart of the Chianti hills, Al Gelso Bianco offers families a laid-back yet stylish countryside base. Think: olive groves, vineyards, a sparkling pool, a dedicated kids’ area, and on-site cooking classes for all ages. It’s ideal for families who want both outdoor adventures and a touch of resort feel — especially in a region teens and tweens will want to explore.

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Keep Reading

Planning a longer trip? See our complete Italy Family Travel Guide for more itineraries and kid-friendly destinations. Get help booking family-friendly villas and hotels.

For family-friendly recommendations, check out our guide to visiting Tuscany with Kids. If you have more time to spend in Italy, discover the best of Rome with kids. And, if you need additional ideas for your next vacation, explore our favorite European destinations.

Planning a multi-country trip to Europe? Consider 2-weeks in Croatia.

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