Tuscany has a special way of captivating your heart. From rolling hills dotted with olive groves and cypress trees to medieval hilltop towns and sunsets that seem to last longer, it’s my absolute FAVORITE destination in the world (if I had to pick one). I’ve never felt more at peace on a trip, and time truly seems to slow down here. Staying at a vineyard, with the views, wine, pool, and overall calmness, is truly one of the biggest highlights of the time I have spent in Italy.
Tuscany is famous for its rich history, world-class wines, and Renaissance art. Whether you’re planning to explore Tuscany by visiting vineyards in Chianti, marveling at Florence’s art and architectural wanders, see the Leaning Tower of Pisa, or wandering the charming streets of San Gimignano and Montepulciano, beauty and culture are everywhere. The right hotel will allow you to experience the best of Tuscany without wasting too much time on the road. In this guide, I’m sharing my top picks for where to stay, so you can enjoy this magical region to the fullest.
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Where to Stay in Tuscany Region
Before we dive into specific accommodations, let’s take a look at Tuscany’s layout. The region is located in central Italy and is made up of several provinces, each with its own landscapes, towns, and experiences. From Florence’s rich art and culture to the wine-soaked hills of Chianti and the peaceful beauty of Val d’Orcia, each part of Tuscany has something unique to offer. Just keep in mind the distances between towns and vineyards to plan your time accordingly. In this guide, I’ll walk you through Tuscany and help you find a place to stay that fits your travel style and interests.
Note: I highly recommend renting a car to explore the Tuscan countryside. It makes getting from one spot to the next so much easier and more flexible. We picked ours up at the Florence airport (it’s just a quick cab ride if you come by train!), and the best part is it’s on the outskirts of the city, so you skip the hassle of driving in Florence itself and are practically already in the countryside. Don’t worry, Italians drive on the right side of the road, just like in the US! Once you’re out in the hills, driving is easy and gives you the freedom to explore at your own pace. It’s the best way to see Tuscany!
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Where Is The Tuscany Region In Italy
Tuscany sits right in the heart of Italy, bordered by Liguria, Emilia-Romagna, Umbria, Marche, Lazio, and the Tyrrhenian Sea. This central location gives Tuscany a diverse landscape, with everything from rolling inland hills to beautiful coastline, and it makes it easy to explore.
Popular Areas to Visit in Tuscany
- Florence
A hub of art, culture, and history with must-see sites like the Uffizi Gallery and Michelangelo’s David. - Chianti
Famous for vineyards and rolling hills, perfect for wine lovers and scenic drives. - Val d’Orcia
Known for stunning landscapes, cypress-lined roads, and charming towns like Pienza and Montalcino. - Siena
A medieval gem with beautiful piazzas, historic sites, and rich culture. - San Gimignano
Famous for its medieval towers and picturesque streets, offering views of Tuscany’s vineyards. - Pisa
Home to the Leaning Tower, plus historic buildings and Tuscan charm. - Cinque Terre
A coastal wonder just outside Tuscany, with colorful villages, hiking trails, and stunning sea views. - Apuan Alps
Rugged mountains perfect for hiking, climbing, and enjoying dramatic views.
Thanks to its central location and excellent transport links, Tuscany is easy to get to and get around, making it ideal whether you want to relax or stay active with plenty of adventures.
Is Tuscany Region Safe?
Yes, Tuscany is generally very safe for travelers! The region has a low crime rate, especially in smaller towns and rural areas, where tourism and local life blend together seamlessly. Florence, Siena, and Pisa are well-patrolled. But, like any popular destination, it’s smart to stay alert in crowded areas and keep an eye out for pickpockets near major tourist attractions and train stations. Whether you’re wandering through the countryside or exploring the historic city centers, Tuscany offers a relaxed, safe environment for solo travelers, couples, and families. During our visit, we saw tons of families at vineyards, and I definitely plan on bringing my children here someday!
Where Is The Best Place To Stay In Tuscany Region
Castello Vicchiomaggio
If you’re looking for the perfect place to stay in the heart of the Chianti region, Castello Vicchiomaggio is everything you could dream of and more. Nestled among the rolling hills of Greve in Chianti, this stunning property offers panoramic views, award-winning wines, and the ultimate Tuscan getaway experience. We had the pleasure of staying on the property. And I can honestly say it was one of the highlights of our trip. If I could go back tomorrow, I would in a heartbeat.
The wine tasting took place on a gorgeous terrace overlooking the vineyard, with sweeping views of the countryside that made each sip feel extra special. There’s something about sipping fine wine while watching the sun set over endless hills that truly embodies the magic of Tuscany.
The property itself is a perfect mix of charm and luxury.
Our room was spacious, peaceful, and beautifully appointed, offering everything you need for a relaxing stay. The real highlight was the infinity pool that overlooked the Tuscan hills—imagine soaking in the Tuscan sun during golden hour, with a glass of wine in hand. Each morning, we were treated to a breakfast spread brimming with fresh fruit, pastries, and savory bites that fueled us up for a day of adventure.
Beyond the comfort and beauty of the property, Castello Vicchiomaggio is the ideal home base for exploring the Chianti Classico region. After long afternoons of wine tasting and wandering the picturesque streets of nearby towns, coming back to this peaceful retreat felt like a dream. Whether you’re after a romantic escape, a wine-lover’s paradise, a family trip, or simply a place to unwind and soak in Tuscany’s beauty, Castello Vicchiomaggio is everything you’re looking for and more.
- Best for: Staying in wine country, infinity pool views, on-site dining
- Location: Greve in Chianti
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Borgo Santo Pietro
If you’re looking for a luxurious, five-star escape in Southern Tuscany, Borgo Santo Pietro is the ultimate retreat. Situated near Siena, just over an hour from Florence, this estate blends historic charm with modern comfort. The property offers individually designed rooms, private pool suites, and exclusive villas, all surrounded by vineyards, olive groves, and beautiful gardens.
Dining here is a treat—whether you’re enjoying gourmet meals at the Michelin-starred Saporium or savoring a more casual bite at Trattoria Sull’Albero. You can indulge in spa treatments, take part in wine tastings, or even explore the stunning countryside on Vespas. The resort is not only luxurious but also safe and accessible. They have airport transfers and private parking available for added convenience.
- Best for: Luxury, Michelin-star dining, private villas, wellness experiences
- Location: Near Siena, about an hour from Florence
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Photo credit: Borgo Santo Pietro
Foresteria Castello di Verrazzano
Foresteria Castello di Verrazzano is a peaceful agriturismo nestled in the heart of Chianti, offering the perfect Tuscan countryside experience. This charming retreat provides rustic double rooms and apartments, all filled with that cozy Tuscan farmhouse charm you can’t get enough of. The daily buffet breakfast is a great way to start your day. And the garden lounging areas offer a serene spot to relax in between exploring the countryside.
With wine tastings and private tours at the adjacent Castello di Verrazzano, this location makes it the perfect base for wine lovers and anyone seeking an authentic Tuscan experience. While we didn’t stay here, we did visit the castle for a tour and lunch with wine pairings. It quickly became one of our favorite experiences in Tuscany! With that kind of experience right on-site, this would absolutely be an amazing place to stay.
- Best for: Wine lovers, authentic Tuscan experience, countryside charm
- Location: In the heart of Chianti
Get Directions to Foresteria Castello di Verrazzano
Foresteria Castello di Verrazzano
Querceto di Castellina
Nestled just outside the charming hilltop town of Castellina in Chianti, Querceto di Castellina offers a serene and picturesque stay in the heart of wine country. Easily accessible from both Florence and Siena, this beautiful estate features cozy apartments and suites that blend rustic elegance with modern amenities, all complemented by private outdoor spaces.
Enjoy the seasonal pool and wine tastings at the on-site winery, where you can savor the best of Chianti’s world-renowned wines. With its peaceful setting and family-friendly atmosphere (crib rentals available at no extra cost!), Querceto di Castellina is the perfect base for exploring the Chianti region. It’s also reasonably priced, making it an excellent option for families or couples seeking a relaxing getaway in Tuscany.
- Best for: Wine tastings, reasonably priced, family-friendly stays, exploring Chianti
- Location: Just outside Castellina in Chianti, easily accessible from Florence and Siena
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Photo credit: Querceto di Castellina
Cantagrillo Boutique Resort
Cantagrillo Boutique Resort is a charming agriturismo located just outside Vinci (Leonardo da Vinci’s hometown!), surrounded by vineyards and olive groves, and only a short drive from Florence. This peaceful retreat offers elegantly styled rooms and suites that perfectly blend comfort and Tuscan charm.
Start your day with a delicious continental breakfast. Then relax by the seasonal outdoor pool or unwind on the shared terrace, taking in the stunning views of the surrounding countryside. Safe, accessible, and with a serene atmosphere, Cantagrillo Boutique Resort is the perfect place to escape and soak in the beauty of Tuscany.
- Best for: Tranquil countryside escape, vineyard views, relaxation
- Location: Outskirts of Vinci, near Florence
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Photo credit: Cantagrillo Boutique Resort
Castello di Vicarello
Castello di Vicarello is a luxurious, 12th-century castle nestled between Florence and Rome. If you’ve been researching Tuscany on Instagram, chances are you’ve come across the stunning shots of their outdoor dining terrace—trust me, I’ve saved more than a few of these images to my inspiration boards! This intimate estate offers uniquely designed suites and a private villa, blending rustic charm with modern luxury. Some suites even come with private terraces or outdoor Jacuzzis, making it the perfect spot to relax and unwind.
During your stay, you can enjoy farm-to-table dining, cooking classes, and wine tastings from the estate’s own vineyard. There’s also a range of experiences to immerse you in the region’s beauty. Like truffle hunting, horseback riding, and rejuvenating spa treatments surrounded by olive trees. With stunning pools, manicured gardens, and that serene, private atmosphere, Castello di Vicarello is the ideal destination for a romantic or peaceful countryside escape.
- Best for: Romantic getaways, immersive experiences, luxury countryside retreat
- Location: Between Florence and Rome, easily accessible by car
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Photo credit: Castello di Vicarello
Agriturismo Villa Buoninsegna
Agriturismo Villa Buoninsegna is a beautifully restored 17th-century estate in the Tuscan countryside, just 30 minutes from Siena. Surrounded by lush olive groves and vineyards, this charming agriturismo offers spacious B&B rooms and cozy self-catering apartments. And are all equipped with modern comforts in a peaceful and secure setting.
What makes this place even more special? It’s incredibly budget-friendly! With its reasonable pricing, Villa Buoninsegna is perfect for travelers who want an authentic Tuscan experience without breaking the bank. Spend your days relaxing by one of the two outdoor pools. Savor local wine and olive oil tastings, or explore nearby thermal baths and historic hill towns. The property is easy to access by car. They have free parking and scenic walking trails throughout the estate for you to enjoy.
- Best for: Budget-friendly stays, relaxing countryside escape, wine and olive oil tastings
- Location: 30 minutes from Siena, surrounded by vineyards and olive groves
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Photo credit: Agriturismo Villa Buoninsegna
Lupaia
Lupaia is a luxury agriturismo perched on a hilltop near Montepulciano, offering panoramic views of Tuscany’s stunning Val d’Orcia. This place is one of my TOP recommendations for a reason: it’s the whole Tuscany experience rolled into one! The estate features uniquely styled rooms and suites across beautifully restored farmhouses, combining modern comforts with a strong sense of privacy and tranquility.
During your stay, you can unwind at the seasonal infinity pool, indulge in spa treatments, or get in a workout at the fitness room. The on-site restaurant serves gourmet meals made with locally sourced ingredients, offering the true flavors of Tuscany. Accessible by car with free parking, Lupaia is also ideally situated for day trips to Siena and the surrounding hill towns. With warm, attentive service and a serene atmosphere, it’s the perfect blend of rustic charm and refined hospitality.
- Best for: Luxury stays, panoramic views, spa treatments, gourmet dining
- Location: Near Montepulciano, with easy access to Siena and surrounding hill towns
Photo credit: Lupaia
Hotel More di Cuna
Hotel More di Cuna is a cozy boutique hotel housed in a beautifully restored farmhouse just outside Monteroni d’Arbia, a short drive from Siena. Offering charming Tuscany-style rooms at budget-friendly prices, this hotel is perfect for travelers looking for where to stay in Tuscany on a budget. Think comfort without the high price tag.
Conveniently located along the historic Via Francigena, it provides a peaceful, secure setting with easy access to Tuscany’s major sites. Each room is equipped with modern amenities like air-conditioning and Wi-Fi. Enjoy a meal at the hotel’s restaurant, grab a drink at the bar, or sip coffee in the charming coffee shop. The garden terrace is perfect for relaxing and soaking in the Tuscan atmosphere.
- Best for: Budget-friendly stays, easy access to major sites, cozy atmosphere
- Location: Just outside Monteroni d’Arbia, a short drive from Siena
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Photo credit: Hotel More di Cuna
Villa Le Barone
Villa Le Barone is a stunning Renaissance estate turned boutique hotel, nestled in the heart of Chianti, between Florence and Siena. Surrounded by vineyards, olive groves, and rose gardens, it’s pure Tuscan magic. The rooms and suites offer all the modern comforts with that classic, peaceful villa charm.
You’ll never run out of ways to unwind here, from the heated saltwater infinity pool (total pool goals) to tennis, biking, and exploring the gorgeous grounds. Dining is a highlight with farm-to-table Tuscan dishes, daily breakfasts on the terrace, and even cooking classes and wine tastings. If you’re looking for a peaceful yet luxurious base to explore Tuscany, Villa Le Barone is the perfect spot to call home.
- Best for: A mix of historic charm and modern luxury, an infinity pool and tennis courts
- Location: In the heart of Chianti, between Florence and Siena
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Related: Tuscany Itinerary
Photo credit: Villa Le Barone
Como Castello del Nero
COMO Castello del Nero is the ultimate splurge for those looking to experience true Tuscan luxury. Set in the Chianti hills between Florence and Siena, this castle on a private estate offers the perfect serene retreat. The rooms and suites elegantly blend historic architecture with modern design, all with stunning views of vineyards, olive groves, and the rolling Tuscan countryside.
For relaxation, the COMO Shambhala Retreat is a must-visit, featuring thermal suites, a heated outdoor pool, a yoga pavilion, and extensive wellness services. Dining here is just as exquisite with options like La Torre, La Taverna, and The Pavilion. If you’re looking for the perfect combination of luxury, comfort, and authentic Tuscan charm, COMO Castello del Nero delivers an unforgettable experience.
- Best for: Luxury stays, wellness retreats, stunning views
- Location: Between Florence and Siena, in the Chianti hills
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Photo credit: Como Castello del Nero
Castello di Casole
Belmond Castello di Casole is the ultimate luxury getaway, set in the private Tuscan countryside near Siena. The best part? It’s easy to get to by car or private transfer, making it a perfect base for your Tuscan escape. The property itself is absolutely stunning, offering elegant rooms, suites, and private villas that combine historic charm with all the modern comforts you could dream of.
You’ll find plenty of ways to relax and unwind here—from lounging by the infinity pool to indulging in spa treatments. If you’re up for some adventure, there are scenic hiking and biking trails to explore all across the estate. Dining options include the delicious Tuscan cuisine at Tosca and cocktails at Bar Visconti. Plus, there’s the option for immersive experiences like cooking classes, truffle hunting, and wine tastings, all to help you dive deeper into the Tuscan way of life.
Safe, serene, and full of atmosphere, Castello di Casole is the perfect spot for an unforgettable escape in the heart of Tuscany.
- Best for: Luxury, immersive experiences, breathtaking views
- Location: Near Siena, in the private Tuscan countryside
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Photo credit: Castello di Casole
Castello di Velona
Castello di Velona is a luxurious castle resort, spa, and winery perched above the Val d Orcia near Montalcino, a UNESCO World Heritage Site. This peaceful retreat is nestled in the heart of Tuscany’s Brunello wine region, offering stunning views and an unforgettable experience. The rooms and suites are elegant, with some featuring private terraces and thermal spring-fed bathtubs, perfect for unwinding.
The wellness center is a highlight, with thermal pools and vineyard-inspired treatments to help you relax. Dining at Settimo Senso offers gourmet Tuscan cuisine paired with estate wines. And you can also enjoy curated experiences like cooking classes, truffle hunting, horseback riding, and even hot air ballooning.
Whether you’re seeking relaxation or adventure, Castello di Velona is the ultimate Tuscan escape, blending luxury, history, and breathtaking views.
- Best for: Luxury, wine lovers, wellness retreats
- Location: Near Montalcino, in Tuscany’s Brunello wine region, a UNESCO World Heritage Site
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Photo credit: Castello di Velona
La Bandita Townhouse
La Bandita Townhouse is a chic boutique hotel located in the historic center of Pienza, blending a former convent’s rustic charm with modern design. You can enjoy amenities like a mini bar with complimentary soft drinks, and a laundry service. The Townhouse Caffè serves seasonal Italian dishes in a relaxed courtyard setting. Easily accessible by car with nearby parking outside the town walls, it offers a safe and tranquil base for exploring the UNESCO-listed town and surrounding countryside.
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Photo credit: La Bandita Townhouse
Hotel Bel Soggiorno
Hotel Bel Soggiorno is the perfect blend of convenience and charm, located right in San Gimignano, with breathtaking views of the Tuscan countryside. This hotel gives you the best of both worlds—you’re just a short walk from the town’s iconic medieval center. Yet, you can also enjoy the serenity of the surrounding hills.
The hotel offers rooms with options for either countryside views or city views, so you can pick your perfect setting. Whether you’re waking up to the rolling hills of Tuscany or the beautiful city skyline, the views here will make your stay even more magical.
San Gimignano is a UNESCO World Heritage town, famous for its medieval towers and charming cobblestone streets. It’s often referred to as the “Manhattan of Tuscany” due to its impressive skyline of towers that date back to the 12th century. Staying at Hotel Bel Soggiorno gives you easy access to explore this historic gem while also providing a peaceful retreat when you’re ready to relax.
- Best for: Stunning views, central city location, exploring San Gimignano
- Location: Right in San Gimignano, walking distance to the historic center
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No matter where you choose to stay in Tuscany, I can guarantee you’re going to have the best time.
Whether it’s in a luxury villa overlooking the rolling hills, a cozy agriturismo nestled among vineyards, or a charming boutique hotel in a historic town, Tuscany will steal your heart. I truly believe it’s the most magical place in the world, and it’s somewhere I’ll continue to return to again and again.
If you’re looking for more ways to make the most of your Tuscany experience, check out my Best Things to Do in Italy for even more inspiration. And, of course, if you’re a wine lover, don’t miss my guide on the Best Tuscany Vineyards to find the perfect spots for wine tastings and vineyard tours.
Tuscany is a place you’ll never forget—and I’m sure, like me, you’ll keep coming back for more.
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