Best Towns to Stay in Tuscany: Rolling hills and wine country

Tuscany, the heart of Italy, beckons travelers with its rolling hills, world-class wines, and Renaissance masterpieces. As you plan your Italian sojourn, choosing where to stay can make or break your experience. Did you know that Tuscany attracts over 45 million tourists annually? It’s no wonder, given its blend of history, culture, and natural beauty.

Whether you’re dreaming of a rustic farmhouse nestled in vineyards or a chic city apartment steps from iconic museums, Tuscany offers a tapestry of options. Let’s explore the top towns to base yourself in and uncover hidden gems that promise an authentic Tuscan experience.

Table Of Contents

The Top 5 Best Towns to Stay in Tuscany
Two Towns to Avoid Staying
Conclusion

The Top 5 Best Towns to Stay in Tuscany

1. Siena: Medieval Magic

Step back in time in Siena, a UNESCO World Heritage site known for its medieval cityscape and the famous Palio horse race. The fan-shaped Piazza del Campo is the heart of the city, perfect for people-watching while sipping a cappuccino. Siena offers a more laid-back alternative to Florence, with equally rich history and fewer crowds.

Best places to stay in Siena:

Solo Travel: Alma Domus. A convent-turned-guesthouse offering simple rooms with unbeatable views of Siena’s Cathedral.
Budget-Friendly: Hotel Alma Domus. Clean, comfortable rooms in the heart of Siena, perfect for travelers on a budget.
Couples Escape: Grand Hotel Continental Siena. A romantic 17th-century palazzo with frescoed ceilings and a wine cellar for intimate tastings.
Family-Friendly: Hotel Garden. Surrounded by gardens with a pool, this hotel offers family rooms and is a short drive from the city center.
Group Travel: Villa Elda Boutique Hotel. A charming villa with various room types and a terrace overlooking Siena, suitable for groups.
High-End Luxury: Rosewood Castiglion del Bosco. Located in the UNESCO-listed Val d’Orcia, this exclusive resort offers ultimate luxury in the Tuscan countryside.

2. San Gimignano: Towers and Treasures

Often called the “Manhattan of the Middle Ages” for its striking towers, San Gimignano is a postcard-perfect hill town. Its well-preserved medieval architecture and surrounding vineyards producing the renowned Vernaccia white wine make it an ideal base for those seeking charm and tranquility.

Best places to stay in San Gimignano:

Solo Travel: Le Undici Lune. A small, friendly B&B within the town walls, offering personalized service for solo travelers.
Budget-Friendly: Hotel L’Antico Pozzo. A centrally located hotel with reasonable rates and a rooftop terrace for sunset views.
Couples Escape: Villasanpaolo Resort & Spa. A romantic retreat just outside town, featuring a spa and panoramic views of San Gimignano.
Family-Friendly: Fattoria Voltrona. An agriturismo with family apartments, a pool, and activities like horseback riding.
Group Travel: Agriturismo Il Segreto di Pietrafitta. Rustic apartments on a working farm, perfect for groups wanting an authentic Tuscan experience.
High-End Luxury: Borgo Pignano. An 18th-century villa turned eco-friendly luxury resort, offering cooking classes and yoga retreats.

3. Lucca: Walled Wonder

Encircled by Renaissance-era walls, Lucca offers a unique stay in Tuscany. Bike along the ramparts, explore hidden gardens, and lose yourself in narrow lanes lined with boutiques and cafes. Lucca’s central location makes it perfect for day trips to Pisa or the Versilia coast.

Best places to stay in Lucca:

Solo Travel: Ostello San Frediano. A centrally located hostel in a historic building, ideal for solo travelers on a budget.
Budget-Friendly: Hotel Ilaria & Residenza dell’Alba. Set in a former church, offering comfortable rooms and bike rentals to explore Lucca’s walls.
Couples Escape: Palazzo Dipinto. A boutique hotel in a restored 16th-century palazzo, blending history with modern comforts.
Family-Friendly: Al Porto di Lucca B&B. A welcoming B&B with family rooms and a lovely garden, just outside the city walls.
Group Travel: Villa Michaela. A stunning 18th-century villa accommodating up to 35 guests, perfect for large groups or events.
High-End Luxury: GH Principe di Piemonte. A grand hotel on Viareggio’s promenade, offering a rooftop pool and Michelin-starred dining.

4. Montepulciano: Hilltop Haven

Perched high on a limestone ridge, Montepulciano is synonymous with wine excellence. This picturesque town offers breathtaking views of the Val d’Orcia and Val di Chiana valleys. It’s an excellent base for wine enthusiasts and those looking to explore southern Tuscany’s lesser-known corners.

Best places to stay in Montepulciano:

Solo Travel: Ostello Gatto Osmannoro. A cozy hostel in the heart of Montepulciano, perfect for solo travelers exploring wine country.
Budget-Friendly: Albergo Duomo. Simple rooms with stunning views, located steps from Montepulciano’s main square.
Couples Escape: Villa Cicolina. A romantic 16th-century villa with a panoramic pool, perfect for couples seeking seclusion.
Family-Friendly: Agriturismo Pescaia. Family-run farm stay offering apartments, a pool, and activities for children.
Group Travel: Borgo Tre Rose. A restored medieval village turned resort, ideal for groups wanting to immerse in Tuscan life.
High-End Luxury: Monteverdi Tuscany. An exclusive hamlet turned boutique hotel, offering unparalleled luxury in the Val d’Orcia.

5. Florence: The Renaissance Jewel

Florence, Tuscany’s capital, is a living museum where every cobblestone tells a story. Staying here puts you at the epicenter of Renaissance art and architecture. The Duomo’s iconic dome dominates the skyline, while world-renowned galleries like the Uffizi are just a stone’s throw away. Florence is ideal for culture vultures and foodies alike, with its bustling markets and traditional trattorias.

Best places to stay in Florence:

Solo Travel: Hostel Archi Rossi. Located near the train station, this vibrant hostel offers clean rooms, free walking tours, and a chance to mingle with fellow travelers.
Budget-Friendly: Hotel Palazzo Guadagni. Set in a 16th-century palace, this affordable gem boasts a rooftop terrace with stunning Duomo views.
Couples Escape: Portrait Firenze. Overlooking the Arno River and Ponte Vecchio, this luxury boutique hotel offers romantic suites with personalized service.
Family-Friendly: Residence Hilda. Spacious apartments with kitchenettes, close to major attractions, perfect for families wanting a home away from home.
Group Travel: Palazzo Nikki. A restored renaissance palace with multiple bedrooms and a communal courtyard, ideal for larger groups or families.
High-End Luxury: Four Seasons Hotel Firenze. Set in a former palace and convent, it offers opulent rooms, a spa, and the largest private garden in Florence.

For more about Florence and more recommendations on where to stay – be sure to check out our Florence neighborhoods guide!

Two Towns to Avoid Staying

While Tuscany is generally delightful, consider avoiding extended stays in:

Pisa: Beyond the Leaning Tower, Pisa can feel touristy and lacks the charm of other Tuscan towns. It’s better as a day trip.

2. Viareggio: Though popular for its beaches, it can be overcrowded in summer and lacks the quintessential Tuscan atmosphere found inland.

Conclusion

Tuscany’s diverse landscape offers a stay for every type of traveler, from the art-filled streets of Florence to the rolling hills of Val d’Orcia. Whether you’re seeking a romantic getaway, a family adventure, or a solo exploration of Italy’s cultural heartland, the perfect Tuscan retreat awaits. Remember, the best place to stay is one that aligns with your travel style and the experiences you seek. So, pack your bags, book your ideal Tuscan stay, and prepare for an unforgettable journey through one of Italy’s most beloved regions. Your Tuscan dream awaits – it’s time to turn it into reality!

Visiting other parts of Italy? Check out our other ‘Best Towns and Neighborhoods to Stay’ pages for a deeper look into the different regions and cities across Italy!