Where to Stay in Tuscany: Best Areas & Hotels + Maps
by Sean Finelli
Last updated on September 11, 2025
You are here: Home/travel-blog/ Where to Stay in Tuscany: Best Areas & Hotels + Maps
Tuscany might be all vineyards and sunsets on Instagram, but where you base yourself changes everything. Some towns are made for wine lovers, others for history buffs, and a few are perfect if you don’t want to rent a car. This guide breaks down where to stay in Tuscany by region, so you can pick the best fit for you.
The Tuscany you see on social media—the one with cypress trees and sun-soaked vineyards—is very real, but it’s not everywhere. Picking the right area is crucial to experiencing the region’s true magic. A car is recommended for exploring, but we’ve also included towns that work for travelers who prefer to use public transit.
Lucca is that Tuscan city everyone tells you to visit on a day trip. Mistake. Stay the night, cycle the 16th-century walls, climb the Torre delle Ore, and watch the crowds vanish after dark. Add Puccini’s birthplace and the Colline Lucchesi vineyards, and you’ve got yourself the most underrated base of Tuscany.
Why Stay in Lucca
Lucca is a fantastic option if you want easy logistics without sacrificing charm.
Connected and convenient. Lucca’s main train station is just a short walk from the historic center, making it easy to pop over to Florence or Pisa.
Flat and walkable: All the highlights—Anfiteatro, churches, towers—fit inside the walls.
Authentic and Low-key: You won’t be bombarded by crowds, and you will find amazing food and a welcoming atmosphere that feels like home.
Hotels in Lucca
Grand Universe Lucca ⭐⭐⭐⭐
History & Design • Rooftop Bar • Wine Cellar
A Renaissance palazzo turned boutique stay with velvet interiors, rooftop cocktails, and Puccini-themed rooms, just steps from Piazza Napoleone.
Siena and Chianti are two sides of the same coin—the first is a medieval city with Gothic cathedrals and horse races, the latter a countryside of vineyards, castles, and hill towns. Stay where you want to wake up, day trip to the other, and you’ll see why they’re best experienced together.
Why Stay in Chianti
Booking a stay in the Chianti wine region or Siena is ideal for travelers who want medieval city charm plus authentic Tuscan countryside hotels.
Wine and agriculture. This region is packed with medieval castles, ancient churches, and wineries to explore. It’s also home to some incredible restaurants that you shouldn’t dare ignore.
Best of both worlds. Siena offers a larger city experience, while the Chianti countryside provides a tranquil retreat.
Slow down. Unlike cities you can breeze through, this area rewards travelers who slow down and settle in.
Car required. A car is essential to explore the area’s smaller towns and vineyards.
Hotels in Chianti & Siena
Villa Medicea di Lilliano ⭐⭐⭐⭐
Wine Tasting • Poolside Views • Cooking Classes
A luxurious estate with elegant, modern suites and a relaxing pool, set on a vineyard with gorgeous views of Florence.
Love what you’re seeing so far, but can’t be bothered to plan it all? Check out these multi-day stays, which pair fabulous B&Bs with curated Tuscan experiences.
Known for its skyline of towers, San Gimignano is one of Tuscany’s most iconic towns and a favorite stop between Florence and Siena. Its medieval center is lively with shops, small museums, and piazzas, while the surrounding hills give you countryside tranquility in minutes.
Why Stay in San Gimignano
San Gimignano offers the perfect mix of local charm and a central location, with plenty to keep you busy while you explore the rest of Tuscany.
Walkable medieval core: You’ll find Romanesque churches, frescoes, towers, and piazzas all within the old city walls.
Proximity to major hubs: With a car, Florence, Siena, and Chianti’s wineries are an easy drive.
Wine isn’t the headline: It’s not in Brunello or Chianti Classico country, but you’ll still find plenty of great restaurants serving Tuscan wine.
Hotels in San Gimignano
Mormoraia ⭐⭐⭐⭐
Pool & Spa • Winery • Tuscan Views
Known for its olive oil and wine production, Mormoraia blends rustic charm with modern comforts just 4 km from San Gimignano.
Deep in the heart of southern Tuscany, Val d’Orcia is a UNESCO World Heritage site known for its perfectly preserved, dreamlike landscape. At its core are the famous hill towns of Pienza and Montepulciano, offering Renaissance-era history and some of the region’s best wine. It’s the definitive destination if you want to experience the authentic beauty of the Tuscan countryside.
Why Stay in Val d’Orcia
Staying in Pienza, Montepulciano, or another town in Val d’Orcia gives you an authentic slice of Tuscan life. It’s a chance to truly experience the best of the region’s scenery and history, just as it’s meant to be seen.
Wine country at its peak: Montepulciano is home to Vino Nobile, and nearby Montalcino pours world-famous Brunello.
Culture with scenery: Pienza’s Piazza Pio II and Palazzo Piccolomini pair history with sweeping countryside views.
Remote but rewarding: It’s less connected by train, but having a car makes the whole region—from vineyards to thermal baths—yours to explore.
Hotels in Val d’Orcia
Capanna Suites ⭐⭐⭐⭐
Infinity Pool • Wine Country • Spa & Wellness
A modern farm stay with a spa, on-site restaurant, and a beautiful outdoor deck overlooking the wine country.
Cortona: Best Area of Tuscany to Stay For Cultural Immersion
If Under the Tuscan Sun made you dream of Tuscany, Cortona is the real-life version—perched high with storybook views and timeless charm. Its Etruscan roots, Renaissance churches, and artisan-filled streets give it depth, while its location makes it ideal for exploring both Tuscany and Umbria. Unlike Florence or Siena, Cortona feels refreshingly unpolished and personal.
Why Stay in Cortona
Staying in Cortona is a fantastic choice if you want to experience the authentic feel of a Tuscan hill town without the day-tripper crowds. Its combination of history and everyday life makes for a memorable trip.
Famous but authentic: Despite Hollywood fame, Cortona still feels like a real town where locals outnumber tour groups.
Culture-packed: From the MAEC Etruscan Museum to Renaissance churches and art-filled piazzas, history is everywhere.
Hilly but rewarding: The steep streets take effort, but the panoramic views and quiet corners more than pay you back.
Hotels in Cortona
Business travelers and football fans alike will find some great Madrid hotel options here.
Villa di Piazzano ⭐⭐⭐⭐⭐
Countryside Views • Historic Villa • Gourmet Dining
A family-run Renaissance villa with gardens, a pool, and farm-to-table dining, just outside Cortona with sweeping countryside views.
Central Location • Historic Building • Private Parking
Perfect for travelers arriving by car, this centrally located hotel blends Renaissance architecture with convenience just steps from Cortona’s main sights.
Choosing where to stay in Tuscany depends on your style of travel. Think about car rental, wine regions, medieval history, or family-friendly towns when picking your base.
Don’t want to rent a car? Stay in Lucca for train connections or Siena for bus access to nearby towns.
Looking for romance? Choose Val d’Orcia for vineyard views or Cortona for sunsets and strolls out of Under the Tuscan Sun.
Wine lover first, everything else second? Base in Chianti or Montepulciano for world-class reds and vineyard stays.
History buff? Stay in San Gimignano or Siena for medieval towers, cathedrals, and museums at your doorstep.
Traveling with kids?Chianti offers countryside villas with space to roam and easy day trips to Siena or Florence.
On a budget?San Gimignano and Lucca have smaller hotels and agriturismi that are easier on the wallet than Florence.
Luxury traveler? Splurge in Val d’Orcia, where restored villas and castles double as 5-star spa hotels with Brunello tastings.
Best Tours and Experiences in Tuscany
Tuscany isn’t just about sipping wine and staring at hills—though that’s highly recommended. A well-planned tour helps you skip the guesswork and dive deeper into the food, history, and scenery. Whether it’s a vineyard visit, guided city walk, or small-group cooking class, tours add insight (and save time) you won’t get wandering on your own.
Avoid staying on the outskirts of major cities like Florence or Pisa in what look like cheap hotels. These areas are often congested, lack the charm of the historic center, and don’t offer easy access to the countryside.
Likewise, skip staying too far off the beaten path unless you’re fine driving everywhere. Remote villages might sound charming, but they lack restaurants, transport, and nightlife. For most travelers, it’s better to base in a town with services and day-trip options than get stuck in the middle of nowhere.
Where To Stay in Tuscany FAQs
What’s the best city to stay in Tuscany for a first-timer?
For first-time visitors, Lucca is an excellent base. It’s a charming walled city with great restaurants, a laid-back vibe, and easy train access to other major cities.
Do you need a car to visit Tuscany?
A car is highly recommended for exploring the countryside, but you can get by without one. Stick to cities with good train connections like Lucca, Florence, or Siena.
Is it better to stay in a city or the countryside in Tuscany?
It depends on your travel style. City stays offer convenience, walkability, and nightlife. Countryside stays provide a more authentic, peaceful experience with stunning views and quiet.
What are the most beautiful towns in Tuscany?
San Gimignano, Montepulciano, Pienza, and Cortona are often cited as the most beautiful hill towns in Tuscany, known for their historic charm and incredible views.
Where should I stay in Tuscany for a romantic trip?
For romance, consider staying in a countryside villa or agriturismo in Chianti or the Val d’Orcia region. They offer secluded luxury, incredible views, and intimate dining experiences.
Is Florence a good base for day trips?
Florence can be a base for day trips, but it’s not the most efficient. Driving in and out of the city is challenging, and train travel is easier from a smaller, more centrally located city.
What’s the most authentic place to stay in Tuscany?
For an authentic feel, consider staying in a town like Cortona or a smaller village in Chianti. These places are less focused on tourism and more on local life.
Are agriturismo stays a good option?
Yes, agriturismo stays are fantastic for a true Tuscan experience. They are working farms that often produce their own wine, olive oil, and food, offering an immersive stay.
Final Thoughts
Tuscany is a place you don’t just visit—you experience it. And your choice of a hotel and a home base is the most important part of that experience. Whether you want to be surrounded by history, vineyards, or quiet country roads, picking the right spot is key. But there’s more to plan than your accommodation!
Sean is a co-founder and owner of The Tour Guy and its subsidiary The Roman Guy. He studied finance and statistics, but that is his "Dr. Jekyll" side! His "Mr. Hyde" is in love with travel, art, history, and culture. Sean has read libraries of historical text and believes that all internet content should come from books. A practice he follows!
