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). If someone asked me where I’d go back to tomorrow, I’d probably say Tuscany without even thinking twice. 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, was 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 wonders, seeing the Leaning Tower of Pisa, or wandering the charming streets of San Gimignano and Montepulciano, beauty and culture are everywhere (literally). After spending way too much time researching where to stay for our own trip, I’m convinced that choosing the right home base makes all the difference. The right hotel lets you 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, along with what I learned while planning our trip and exploring the region ourselves.
Where to Stay in Tuscany Region
Before we dive into specific accommodations let’s take a look at Tuscany’s layout, because to be completely honest, how spread out everything is there had me questioning my sanity while trying to plan this portion of our trip. 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.
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!
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. My personal favorite area for first-time visitors. - 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 of Pisa, 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.
One of the things I loved most about Tuscany is how different each area feels. Even after spending a few days there, I left with a list of places I still wanted to come back and explore. Thanks to its central location, it’s easy to build an itinerary around whatever interests you most, whether that’s wine tasting, medieval towns, hiking, or simply soaking up the Tuscan countryside.
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. During our visit, we saw everyone from couples and friend groups to families with young kids enjoying the vineyards together, and by the end of our trip we were already saying how we can’t wait to come back and bring our own kids here someday.
Where Is The Best Place To Stay In Tuscany Region
Castello Vicchiomaggio
If you’re trying to decide where to stay in Tuscany, this is my top answer. We spent two nights at Castello Vicchiomaggio during our first trip to Tuscany, and looking back, I genuinely don’t think we could have picked a better home base. It’s located right in the rolling hills of Greve in Chianti, and it had everything we were hoping to find like incredible vineyard views, award-winning wines, an onsite restaurant, an infinity pool, and that classic Tuscan atmosphere I’d been dreaming about for years.
I still remember opening the shutters to our room for the first time and seeing the vineyards stretched out in front of us. It honestly looked like a painting. In fact, the photos I took here spent a good three years as my phone’s lock screen background because I just couldn’t get over the views. One of my favorite parts of staying here was that you never even had to leave if you didn’t want to. We enjoyed the complimentary wine tasting included with our stay, spent slow mornings at breakfast overlooking the countryside, relaxed by the infinity pool, and ended the day with dinner and a bottle of wine on the terrace. It was exactly the slower pace I’d hoped Tuscany would have (especially since we were coming from Rome!)
That said, if you do want to explore, the location couldn’t be better. It’s an easy home base for wine tasting around Chianti Classico, visiting nearby towns, and scenic drives through the countryside before returning to somewhere that somehow felt even prettier at the end of the day. When I return to Tuscany (when, not if) this is where I’d stay again without even looking anywhere else!
- Best for: Staying in wine country, infinity pool views, on-site dining
- Location: Greve in Chianti
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Castello Vicchiomaggio (just look at that pool!)
Borgo Santo Pietro
If you’re looking to splurge on a luxury stay in Tuscany (treat yourself!) Borgo Santo Pietro is one of the most beautiful properties you’ll come across. Located near Siena in Southern Tuscany, this five-star estate blends historic charm with modern luxury, offering individually designed rooms, private pool suites, and exclusive villas surrounded by vineyards, olive groves, and beautifully landscaped gardens.
The experience goes far beyond just the rooms. Guests can enjoy Michelin-starred dining at Saporium, a more relaxed meal at Trattoria Sull’Albero, spa treatments, wine tastings, and even Vespa rides through the Tuscan countryside. It’s the kind of place where you could easily spend a few days without ever feeling the need to leave the property at all.
- Best for: Luxury, Michelin-star dining, private villas, wellness experiences
- Location: Near Siena, about an hour from Florence
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Borgo Santo Pietro
Foresteria Castello di Verrazzano
If staying on a working vineyard sounds like your idea of the perfect Tuscany getaway, Foresteria Castello di Verrazzano is definitely one to consider. This peaceful agriturismo sits in the heart of Chianti and offers rustic double rooms and apartments, all with that classic Tuscan farmhouse charm. Guests can enjoy a daily breakfast before heading out to explore the surrounding countryside, and the garden lounging areas look like the perfect place to slow down with a glass of wine after a day of exploring.
One of the biggest reasons I’d recommend this property is its location. With wine tastings and private tours at the adjacent Castello di Verrazzano, it makes an incredible home base for wine lovers looking to fully experience the Chianti region. While we didn’t stay here, we did spend half a day at Castello di Verrazzano for their Wine and Food Experience, and it ended up being one of our favorite memories from all of Italy. Between the incredible lunch, the historic cellars, and the beautiful setting, I’d have absolutely no hesitation booking a stay here on a future trip.
- Best for: Wine lovers, authentic Tuscan experience, countryside charm
- Location: In the heart of Chianti
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Foresteria Castello di Verrazzano
Querceto di Castellina
If your idea of the perfect Tuscany stay includes waking up surrounded by vineyards, Querceto di Castellina is definitely one to have on your radar. Located just outside the charming hilltop town of Castellina in Chianti, this beautiful estate offers cozy apartments and suites that blend rustic charm with modern comforts, each with its own private outdoor space.
There is a seasonal pool (a must!) and wine tastings at the on-site winery, making it easy to experience the best of Chianti without venturing too far. It’s also one of the more reasonably priced options on this list, and with its relaxed atmosphere and family-friendly accommodations (including complimentary cribs), it’s a great choice for both couples and families looking to explore the Chianti region.
- 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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Querceto di Castellina
Cantagrillo Boutique Resort
If you’re looking for a peaceful countryside escape not too far from Florence, Cantagrillo Boutique Resort is a beautiful option. Located just outside Vinci (yes, Leonardo da Vinci’s hometown!), this peaceful agriturismo is surrounded by vineyards and olive groves while still being an easy drive from the city.
Guests can start the day with a continental breakfast before relaxing by the seasonal outdoor pool or unwinding on the shared terrace overlooking the Tuscan countryside. If you’re hoping for a quieter stay where you can slow down and enjoy the scenery (I know I usually am), this looks like a wonderful place to do exactly that.
- Best for: Tranquil countryside escape, vineyard views, relaxation
- Location: Outskirts of Vinci, near Florence
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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 inspo 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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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 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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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 after a lot of research 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, which, as I’ve mentioned before, is essential.
- Best for: Luxury stays, panoramic views, spa treatments, gourmet dining
- Location: Near Montepulciano, with easy access to Siena and surrounding hill towns
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 classic Tuscany-style rooms at budget-friendly prices, this hotel is perfect for travelers looking for where to stay in Tuscany on a budget (who doesn’t love comfort without a 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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Hotel More di Cuna
Villa Le Barone
Villa Le Barone is a stunning Renaissance estate turned boutique hotel right in the heart of Chianti, between Florence and Siena. Surrounded by vineyards, olive groves, and rose gardens, it’s truly pure Tuscany. 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
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.
- Best for: Luxury stays, wellness retreats, stunning views
- Location: Between Florence and Siena, in the Chianti hills
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Como Castello del Nero
Castello di Casole
Belmond Castello di Casole is the ultimate luxury getaway, set in the private Tuscan countryside near Siena (a fantastic location in my opinion!) 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.
- Best for: Luxury, immersive experiences, breathtaking views
- Location: Near Siena, in the private Tuscan countryside
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Castello di Casole
Castello di Velona
When I think of Tuscany, I often picture a luxurious castle resort, and Castello di Velona is that, along with a spa, and winery. It’s 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 another 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 (hello, bucket list item I didn’t know I had before)
- 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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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 (unheard of back home) 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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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” (sign me up!) 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 a luxury villa overlooking the rolling hills, a cozy agriturismo surrounded by vineyards, or a boutique hotel in one of Tuscany’s beautiful hilltop towns, where you stay really does shape the whole experience. Tuscany is still my favorite destination I’ve ever traveled to, and if someone asked me where I’d go back tomorrow, my answer wouldn’t even require a second thought.
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.
Follow along on Instagram for more travel tips, behind-the-scenes moments, and my latest adventures!
Planning a bigger Italy itinerary? Here are a few more of my guides that might help:
Rome
- How to Pack for a Trip to Rome
- Best Restaurants in Rome
- Where to Stay in Rome
- Visiting the Vatican
- How to Visit the Colosseum
