Where is the best place to stay in Tuscany?
By Francesco Guarguaglini. January 26, 2023
In the centre north of the Italian Peninsula, the region of Tuscany (“Toscana” in Italian) is known worldwide for its gentle hills, vineyards, olive groves, sunny beaches, ski resorts on the Apennine mountains and stunning historical and artistical heritage cities like Florence, Siena, Pisa, Arezzo. With all that choice, what is left for you is to be guided towards the best places to stay in Tuscany.
The famous Chianti region can often be the best choice, as it’s located in an area, between Siena and Florence, from which you can comfortably reach any other part of Tuscany. Not only that, you can also indulge in wine tastings and farm visits around the bucolic hills of Chianti, Val D’Orcia or Montepulciano. If you were thinking about chilling on a sunny beach and having delicious typical Italian food during the evenings, then Livorno and the Isola d’Elba are there for you!
A city break would suit your schedule better? Think about going through the streets of the birthplace of Renaissance, Florence, with all its fashion boutiques, art galleries and osterias, the Gothic beauty Siena or the iconic Pisa, with its leaning tower.
If you are interested in where to stay in Tuscany, you may also be interested in where to stay in Cinque Terre, where to stay in Venice and where to stay in Milan.
Best places to stay in Tuscany
Chianti
Wine Enthusiasts / Nature Seekers / Cultural Explorers
Located right in the heart of Tuscany between the cities of Florence and Siena, the area of Chianti is synonymous with excellent wine. A region of gentle green hills covered with lush vineyards, of ancient olive groves and small ochre coloured villages, it’s a great choice for a Tuscan summer vacation and makes an excellent base for travelling around the area, or for making trips to the cities of both Florence and Siena.
You’ll find all kinds of accommodation here, from Tuscan farmhouses and guesthouses to luxury hotels, some of which come complete with spas. Famous for its wine production, if you love wine you’ll be in heaven in Chianti. Not only are there many wineries to explore and a multitude of wines to taste, but some of the wineries even open their doors for overnight guests.
If you choose to stay in the Chianti Region, even though you’re right in the middle of the countryside, it never feels totally remote. It’s always filled with many holidaymakers, especially during the summer, when visitors flock to tour the hill villages.
Recommended hotels in Chianti:
Castello di Spaltenna: Nestled amidst the rolling hills of Chianti, Castello di Spaltenna offers a luxurious retreat in a historic castle setting. Located in Gaiole, this hotel boasts elegantly appointed rooms, a serene spa, and a gourmet restaurant. Perfect for couples seeking a romantic getaway, Castello di Spaltenna offers breathtaking views, a tranquil ambiance, and world-class hospitality.
Borgo San Felice: Experience Tuscan charm at Borgo San Felice, a picturesque hotel nestled in the heart of Chianti, near Castelnuovo Berardenga. This restored medieval village offers spacious rooms, a wine cellar, and an outdoor pool set amidst vineyards. Ideal for wine enthusiasts and food lovers, Borgo San Felice provides wine tastings, cooking classes, and Michelin-starred dining for an authentic Tuscan experience.
Castello di Ama: Immerse yourself in the beauty of Chianti’s countryside at Castello di Ama, a boutique hotel situated in the quaint village of Ama. With elegantly furnished rooms, an art gallery, and a wine estate, this hotel is a haven for art and wine enthusiasts. Perfect for culture seekers, Castello di Ama offers guided tours of the estate, art exhibitions, and wine tastings amidst the stunning vineyards.
Val d’Orcia
Landscape Admirers / Photographers and Artists / Wellness and Relaxation Seekers
Val d’Orcia, along with Chianti, is one of the two most popular destinations for both Italian and foreign visitors to Tuscany. An area of cultivated hills and picturesque towns and villages, it extends from the hills to the south of Siena to Monte Amiata.
If you’re planning to explore the Val d’Orcia area, Pienza makes an ideal central base, as it’s in easy reach of Montalcino, San Quirico d’Orcia, Monticchiello, Bagno Vignoni, and even Montepulciano in Val di Chiania. Pienze is also a great place to stay if you love Italian food, as it is famous for its extremely tasty Pecorino cheese, handmade pasta and of course the local wine, plus it’s full of fantastic restaurants and osterie serving delicious local foods.
Recommended hotels in Val d’Orcia:
Castello Banfi - Il Borgo: Located amidst the rolling hills of Val d’Orcia, Castello Banfi - Il Borgo is a luxurious retreat in Montalcino. This medieval castle turned hotel offers elegantly furnished rooms, a spa, and an outdoor pool with panoramic views. Ideal for wine enthusiasts, Castello Banfi produces its own award-winning wines, and guests can enjoy wine tastings and vineyard tours for an immersive experience in Tuscan wine culture.
Adler Thermae Spa & Relax Resort: Set in the heart of Val d’Orcia, near Bagno Vignoni, Adler Thermae Spa & Relax Resort is a wellness haven surrounded by natural hot springs. This luxurious resort features spacious rooms, multiple thermal pools, and a comprehensive spa offering rejuvenating treatments. Perfect for those seeking relaxation and wellness, Adler Thermae provides a range of activities, including yoga classes, guided hikes, and gourmet dining for a truly rejuvenating getaway.
Castiglion del Bosco: Embrace Tuscan charm at Castiglion del Bosco, a picturesque estate in Montalcino. This exclusive resort offers elegant suites and villas, a golf course, and a spa. Guests can enjoy wine tastings, truffle hunting, and farm-to-table dining experiences. Ideal for golf enthusiasts, wine connoisseurs, and nature lovers, Castiglion del Bosco offers a serene and luxurious retreat in the heart of Val d’Orcia.
Southern Tuscany and Montepulciano
Food and Wine Enthusiasts / History and Culture Buffs / Outdoor Enthusiasts
To the south of Siena, the Southern region of Tuscany offers a different look and feel to the Chianti area with its large open fields and rolling hills. It’s home to several popular hill villages, with perhaps the most famous being Montepulciano.
Located in Val di Chiania, the region between Val d’Orcia and Val Tiberina, Montepulciano is an ideal place for holidaymakers who are looking to stay in a hilltown which has lots of facilities. Sitting atop a ridge on Monte Poliziano, it’s reached by a long winding street, the Corso, which snakes its way up the hill stretching for an incredible 11.5 kilometres from Porta Al Prato to the Piazza Grande.
Filled with all kinds of architectural delights, including a 17th-century cathedral, the Church of Saint Agostino, the Oratorio della Misericordia and Montepulciano Castle, it’s especially favoured by holidaymakers who wish to explore the surrounding countryside, but who also enjoy taking in the local architecture and culture. It’s also a popular destination for wine lovers, and the town is most widely known for its Vino Nobile di Montepulciano and Rosso di Montepulciano wines.
Accommodation in Montepulciano
Recommended hotels in Southern Tuscany and Montepulciano:
La Corte del Re: Located in the heart of Montepulciano’s historic center, La Corte del Re is a boutique hotel housed in a beautifully restored Renaissance building. The hotel features elegant rooms, a rooftop terrace with panoramic views, and a wine bar showcasing the region’s renowned Vino Nobile. Perfect for wine lovers and culture enthusiasts, La Corte del Re offers a charming and authentic Tuscan experience.
Castello di Velona Resort: Nestled in the scenic countryside near Montalcino, Castello di Velona Resort is a luxurious retreat set within a medieval fortress. The resort offers spacious rooms and suites, a spa with thermal pools, and an exquisite restaurant overlooking the vineyards. Ideal for those seeking relaxation and indulgence, Castello di Velona provides a serene ambiance, breathtaking views, and world-class amenities.
Relais Villa Grazianella: Situated amidst vineyards and olive groves, Relais Villa Grazianella is a peaceful countryside retreat just a short drive from Montepulciano. This charming villa offers comfortable rooms, a swimming pool, and a garden where guests can unwind and enjoy the beauty of the Tuscan landscape. Perfect for nature lovers and those seeking a tranquil escape, Relais Villa Grazianella provides a serene and idyllic setting.
Arezzo
Art and History Enthusiasts / Antique and Artisan Aficionados / Festivals and Events Seekers
The small city of Arezzo is known for its rich natural and artistic heritage. Starting from Piazza Grande (literal Italian for “big square”), a square that you can clearly recognize in the Oscar winning movie “Life is Beautiful”, you can get lost between the streets of Arezzo, enjoying on the way some of its most famous artists’ creations, like the Basilica di San Francesco.
In the meantime, the small city is plenty of amazingly typical Osterias where to have a deep dive in the delicious cuisine of the town, that mixes the excellent meats of the Val Di Chiana to specialties of the Valdarno area.
Arezzo has, just like Siena, recurrent medieval tournaments that see different quartiers of the city going against each other. While for Siena the tournament is represented by a horse race, in Arezzo is called the “Giostra del Saracino” (Saracen Joust), which can constitute a great entertainment for families.
Recommended hotels in Arezzo:
Hotel Continentale: Located in the heart of Arezzo’s historic centre, Hotel Continentale offers comfortable rooms and a convenient base for exploring the city’s attractions. The hotel provides a warm and welcoming atmosphere, friendly service, and easy access to the famous Piazza Grande and the stunning frescoes of the Basilica of San Francesco. Ideal for history and art lovers, Hotel Continentale is a great choice for those seeking a central location and authentic Italian charm.
Villa Cilnia Boutique Hotel: Situated in the countryside just outside of Arezzo, Villa Cilnia Boutique Hotel is a beautifully restored villa offering a tranquil escape. Surrounded by lush gardens and vineyards, the hotel features elegant rooms, a swimming pool, and a terrace with panoramic views. Perfect for nature enthusiasts and those seeking relaxation, Villa Cilnia provides a serene ambiance and a chance to unwind in a picturesque setting.
Badia di Pomaio: Nestled in the hills overlooking Arezzo, Badia di Pomaio is a unique boutique hotel housed in a former monastery. The hotel combines modern design with historic charm and offers stylish rooms, a gourmet restaurant, and a spa. Guests can enjoy breathtaking views of the surrounding countryside and explore nearby hiking trails. Ideal for food lovers and those seeking a luxurious retreat, Badia di Pomaio provides a blend of tranquility, beauty, and gastronomic delights.
San Gimignano
Architecture and History Enthusiasts / Culinary and Wine Connoisseurs / Art and Culture Seekers
A jump back into the medieval era! San Gimignano is famous for being one of the best maintained examples of urban organization during the medieval era, around 1300. It’s recognised worldwide for being the “Town with the Fine Towers” that make San Gimignano recognizable from a distance, for its Vernaccia di San Gimignano, one of the most peculiar white wines in the world, and for its production of high-end quality saffron.
Located rather close to Florence and embedded in the Chianti area, the village can provide some of the most family friendly experiences there are in Tuscany: wine tastings or delicious typical food are for sure a must, but why not taking a dive in the must-have pool of the accommodation, maybe while sipping a refreshing white wine?
Plenty of touristic structures provide also open air children entertainment facilities, to ensure that also your kids will have a great time.
Accommodation in San Gimignano
Recommended hotels in San Gimignano:
Hotel La Cisterna: Situated in the heart of San Gimignano’s medieval centre, Hotel La Cisterna offers comfortable rooms with stunning views of the town and surrounding countryside. The hotel combines historic charm with modern amenities, providing guests with a rooftop terrace, a bar, and a restaurant serving delicious Tuscan cuisine. Perfect for history enthusiasts and those seeking a central location, Hotel La Cisterna immerses guests in the enchanting atmosphere of San Gimignano.
Relais Santa Chiara Hotel: Located just outside the city walls of San Gimignano, Relais Santa Chiara Hotel offers a peaceful retreat surrounded by vineyards and olive groves. The hotel features elegant rooms, a swimming pool, and a garden where guests can relax and enjoy the serene countryside. Ideal for nature lovers and those seeking tranquillity, Relais Santa Chiara Hotel provides a charming escape with easy access to the historic centre of San Gimignano.
Hotel Sovestro: Nestled in the Tuscan hills, a short distance from San Gimignano, Hotel Sovestro offers comfortable accommodation in a tranquil setting. The hotel boasts spacious rooms, a swimming pool, and a restaurant serving local specialities. Guests can unwind in the peaceful garden or take advantage of the hotel’s bike rental to explore the surrounding countryside. Perfect for nature enthusiasts and those seeking a peaceful retreat, Hotel Sovestro provides a relaxing and authentic Tuscan experience.
Livorno
Coastal and Beach Enthusiasts / Maritime and Historical Exploration / Gastronomic Delights
Some define Livorno the Tuscan Venice, but the city, despite having some great canals and bridges that could remind the “City of Water”, has a completely different soul.It’s one of Italy’s most important port cities, and as such it has a special connection to the sea and its traditions.
From the characteristic coastline of Calafuria, with its rocks and foaming waters perfect for high diving, to the delicacies of its typical dishes, Cacciucco and Ponce alla Livornese among the others, Livorno has always represented a different city from the Renaissance or medieval looking cities around.
A less historical city, but with a strong soul that takes its roots from the sea, Livorno is surely a great place where to have a city break due to its delicious cuisine, its relaxed atmosphere and the variety of spots where to enjoy the sight of the sea.
Recommended hotels in Livorno:
Grand Hotel Palazzo: Located on the picturesque waterfront of Livorno, Grand Hotel Palazzo offers luxurious accommodation and breathtaking views of the sea. The hotel boasts elegant rooms, a rooftop terrace with a swimming pool, and a spa for ultimate relaxation. With its prime location, guests can easily explore Livorno’s historic sites and vibrant promenade. Perfect for discerning travellers and those seeking a touch of luxury, Grand Hotel Palazzo provides a memorable stay in Livorno.
Hotel Rex: Situated in the heart of Livorno, Hotel Rex offers comfortable rooms and a warm, welcoming atmosphere. The hotel provides convenient amenities such as free Wi-Fi, a bar, and a 24-hour front desk. Guests can explore Livorno’s bustling city centre, visit nearby attractions like Fortezza Vecchia, or take a short walk to the beach. Ideal for budget-conscious travellers and those looking for a central location, Hotel Rex offers a comfortable base to discover Livorno.
Hotel Gran Duca: Nestled in Livorno’s historic district, Hotel Gran Duca offers a charming and traditional Italian experience. The hotel features cosy rooms, a courtyard garden, and a restaurant serving delicious Tuscan cuisine. Guests can immerse themselves in Livorno’s rich cultural heritage by exploring the nearby sights, including the Cathedral and the Central Market. Perfect for travellers seeking an authentic local experience, Hotel Gran Duca offers a warm welcome in the heart of Livorno.
Isola d’Elba
Relaxation and Beach Retreat / History and Cultural Exploration / Nature and Outdoor Enthusiasts
The picturesque Isola d’Elba, embedded in the Tuscan archipelago, is known for its small but colourful villages and its quasi-tropical beaches. Whether your target is a romantic couple trip, a family retreat or an adventure with a group of friends, Isola d’Elba can provide you plenty of options!
From the magical but family friendly beaches of Marina di Campo, Biodola, Cavoli to the couple hotspot, La Spiaggia degli Innamorati (The lovers’ beach), you surely can find your spot. If the beach is not your thing, just remember that the Isola d’Elba is also known for the variety of its hiking or mountain biking trails, and most of the touristic resorts also have tennis and football pitches.
Are you a foodie? No problem! One of the most charming thing about Elba is surely the quantity and quality of restaurants available, directly on the beach and often with spectacular views.
Recommended hotels in Isola d’Elba:
Hotel Hermitage: Nestled in a lush Mediterranean park, Hotel Hermitage offers a luxurious retreat on Isola d’Elba. The hotel features elegant rooms with sea or garden views, a private beach, and a swimming pool. Guests can indulge in spa treatments, enjoy fine dining at the on-site restaurant, or take advantage of the various outdoor activities available. Perfect for those seeking relaxation and upscale amenities, Hotel Hermitage offers a tranquil and exclusive experience on Isola d’Elba.
Hotel Villa Ottone: Located in a historic villa surrounded by botanical gardens, Hotel Villa Ottone offers a blend of elegance and natural beauty. The hotel boasts comfortable rooms, a private beach, and an outdoor pool. Guests can explore the enchanting gardens, enjoy gourmet cuisine at the restaurant, or unwind at the spa. Ideal for nature lovers and history enthusiasts, Hotel Villa Ottone provides a charming and peaceful escape on Isola d’Elba.
Hotel Del Golfo: Situated on the picturesque Golfo della Biodola, Hotel Del Golfo offers stunning sea views and direct access to a private beach. The hotel features stylish rooms, a swimming pool, and a restaurant serving Mediterranean cuisine. Guests can enjoy water sports, take scenic walks along the coast, or simply relax by the beach. Perfect for beach lovers and those seeking a seaside getaway, Hotel Del Golfo provides a refreshing and idyllic experience on Isola d’Elba.
Pisa
Gateway to Tuscany / Architectural and Historical Enthusiasts / Cultural and Educational Experience
The city of the leaning tower has been a fascinating touristic destination for decades, and the proximity of the biggest Tuscan airport is surely one of its advantages. Not only, but the availability of thousands of cheap flights from any European city makes Pisa one of the best destinations for a city break or a short (3-4 days) retreat out of country.
While the leaning tower is for sure its notorious hotspot, Pisa can count on several other interesting monuments, such as the Cathedral of Santa Maria Assunta, the Baptistery and the Campo Santo. With great places to eat and have a tasty Aperitivo spread across the extension of the city centre, Pisa can surely please any kind of traveller.
An evening walk aside the river Arno will make you thank yourself for choosing Pisa for a relaxing and enjoyable out-of-town weekend, with your family or as a couple.
Recommended hotels in Pisa:
Grand Hotel Duomo: Located just steps away from the iconic Leaning Tower of Pisa, Grand Hotel Duomo offers a prime location and comfortable accommodations. The hotel features well-appointed rooms, a rooftop terrace with panoramic views, and a restaurant serving delicious Tuscan cuisine. Guests can explore Pisa’s historic centre, visit the nearby Piazza dei Miracoli, or stroll along the Arno River. Perfect for sightseers and those looking for a central location, Grand Hotel Duomo provides a convenient and memorable stay in Pisa.
Hotel Relais dell’Orologio: Situated in a historic building in Pisa’s city centre, Hotel Relais dell’Orologio combines elegance with modern comforts. The hotel offers spacious rooms, a charming courtyard, and a bar serving refreshing drinks. Guests can discover Pisa’s architectural treasures, explore the lively streets, or visit the vibrant Piazza dei Cavalieri. Ideal for culture enthusiasts and those seeking a blend of history and contemporary comfort, Hotel Relais dell’Orologio provides a stylish and convenient base in Pisa.
NH Pisa: Located near the city’s main train station, NH Pisa offers contemporary accommodation and excellent transport links. The hotel features modern rooms, a fitness centre, and a restaurant serving international cuisine. Guests can easily reach Pisa’s attractions, such as the Cathedral and the Botanical Gardens, or take day trips to nearby destinations. Perfect for business travellers and those seeking convenience, NH Pisa offers comfort, accessibility, and a warm hospitality experience.
Florence
Art and Culture Enthusiasts / Shopping and Fashion / Gastronomic Delights
With its glorious architecture and galleries filled to bursting with art and sculptures from the Renaissance Masters, Florence is a city which offers a superb mix of style and culture, and is an ideal place to stay if you’re looking to holiday in a cosmopolitan city, but still have easy access to the Chianti region.
From the iconic Duomo with its red tiled roof and marbled facade, to its high end designer boutiques, gourmet restaurants and designer bistros, there’s no denying the addictive appeal of the city, and its abundance of art galleries make it an especially good destination for art lovers. Here you’ll find the world class galleries of Uffizi, Accademia and Pitti, where some of the finest Renaissance artwork ever produced is on show.
Read more about where to stay in Florence.
Recommended hotels in Florence:
Hotel Brunelleschi: Located in the heart of Florence, Hotel Brunelleschi offers a luxurious stay with a blend of modern comforts and historic charm. The hotel features elegant rooms, a rooftop restaurant with panoramic views, and a wellness centre. Guests can explore Florence’s famous attractions, such as the Duomo and Uffizi Gallery, or simply wander through the picturesque streets. Perfect for art lovers and those seeking a central location, Hotel Brunelleschi provides a sophisticated and unforgettable experience in Florence.
Hotel degli Orafi: Situated on the banks of the Arno River, Hotel degli Orafi combines a prime location with classic elegance. The hotel boasts comfortable rooms, a rooftop terrace overlooking the river, and a bar serving classic Italian cocktails. Guests can immerse themselves in Florence’s rich history by visiting the Ponte Vecchio and the Palazzo Pitti, or indulge in shopping at the nearby boutiques. Ideal for romance and those looking for a riverside retreat, Hotel degli Orafi offers a charming and enchanting stay in Florence.
Hotel Palazzo Vecchio: Located in a historic building near Piazza della Signoria, Hotel Palazzo Vecchio offers a unique blend of Renaissance architecture and modern comfort. The hotel features stylish rooms, a courtyard garden, and a lounge bar. Guests can explore Florence’s cultural gems, including the Florence Cathedral and the Bargello Museum, or relax in the nearby Boboli Gardens. Perfect for history buffs and those seeking a central and atmospheric setting, Hotel Palazzo Vecchio provides a memorable and authentic experience in Florence.
Siena
Historic and Medieval Charm / Festivals and Traditions / Culinary Delights
Perhaps the most enchanting city in Tuscany, Siena always makes the list of Italy’s most visited and popular cities. Famous for its dramatic Gothic architecture, its Duomo and the medieval centre, not to mention museums and art galleries galore, this designated UNESCO World Heritage Site has certainly got everything you could possibly need to keep you happy, if your idea of a perfect holiday involves taking in the cultural attractions and architecture.
The centre of Siena has a wealth of imposing buildings, churches, museums and piazzas, including the popular Piazza del Campo, the site of the former Roman marketplace, which is built on a slope. Add in a lively and vibrant restaurant scene, plus the local confectionary specialities of Panforte, Riacciarelli biscuits, gingerbread and Noto, and you’ll see why Siena is the name on the lips of everyone who’s looking for a sophisticated city break in Tuscany.
Read more about where to stay in Siena.
Recommended hotels in Siena:
Grand Hotel Continental: Located in the heart of Siena’s historic centre, Grand Hotel Continental offers a luxurious stay in a beautifully restored Renaissance palazzo. The hotel features elegant rooms, a rooftop terrace with panoramic views, and a Michelin-starred restaurant. Guests can immerse themselves in Siena’s rich history by exploring the Piazza del Campo and the Siena Cathedral, or simply wander through the charming streets. Perfect for discerning travellers and those seeking a refined experience, Grand Hotel Continental provides an unforgettable stay in Siena.
Hotel Athena: Situated just outside the ancient city walls, Hotel Athena combines modern comforts with Tuscan hospitality. The hotel offers comfortable rooms, a rooftop garden with stunning views of the city, and a restaurant serving traditional Tuscan cuisine. Guests can discover Siena’s cultural treasures, such as the Palazzo Pubblico and the Basilica of San Domenico, or enjoy a leisurely stroll along the medieval streets. Ideal for history enthusiasts and those seeking a convenient location, Hotel Athena provides a warm and welcoming atmosphere in Siena.
Hotel Palazzo Ravizza: Located in a historic 14th-century mansion, Hotel Palazzo Ravizza offers a charming retreat with a touch of old-world elegance. The hotel features individually decorated rooms, a peaceful garden, and a library with antique books. Guests can soak up the authentic atmosphere of Siena, visit the nearby Fortezza Medicea, or relax in the hotel’s courtyard. Perfect for travellers seeking a tranquil and character-filled stay, Hotel Palazzo Ravizza offers a glimpse into Siena’s rich heritage and provides a truly memorable experience.
Our recommended hotels in Tuscany
Use the interactive map to navigate through our recommended hotels in TuscanyNote: Hotel prices can change daily due to promotions, seasons, and demand. Our $ - $$$$ scale shows the overall cost range rather than exact prices.
