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Tuscany is one of the world’s most romanticized destinations. Imagine rolling hills, vineyards, medieval hilltop towns, Renaissance cities packed with art and history, and rustic farmhouses surrounded by olive groves. It’s not hard to see why Tuscany is Italy’s most popular region. Whether you’re on a romantic Italian getaway, a family holiday, or a cultural exploration trip, your choice of where to stay will make or break your Tuscan experience.
Tuscany is not a small region, though, and it’s not all the same. The region stretches from the Apennine mountains down to the Tyrrhenian Sea and the islands. Your location in Tuscany will impact the landscape and vibe you experience, as well as how you get around and where you go to see things.
Your travel style, budget, and interests will also factor into where you stay. In this comprehensive guide, we’ll cover the best areas, towns, and accommodation options in Tuscany. Read on to figure out exactly where to stay in Italy for your dream holiday.
Why It Matters Where You Stay in Tuscany
When you go on a city break, most of your highlights are nearby. If you’re in Florence, you just walk or take the bus to see the main sights. But Tuscania’s main attractions are spread out over valleys, vineyards, medieval hilltop towns, and cities.
Major must-sees include Florence, Siena, Pisa, Lucca, and San Gimignano, but they are all in different parts of the region. And that’s before you get to the wineries of Chianti, the Val d’Orcia valley, the Maremma coastline, or even the islands.
Tuscany is a large region with diverse landscapes and things to do. In fact, it’s rare that you want to stay in only one place if you want to see a lot of the region. It’s common for travelers to split their base between a city and a rural location. Popular pairings are Florence or Siena for the city and Chianti or Val d’Orcia for the countryside. Others prefer to pick one area and do day trips. The good news is that there’s plenty of both.
Best Tuscan Cities to Stay In
If culture, art, and a lively vibe are what you’re after, staying in one of Tuscany’s main cities might be the right choice for you.
Florence: The Heart of Renaissance Tuscany
Florence is Tuscany’s cultural heart and the birthplace of the Renaissance. The city is home to iconic works like Michelangelo’s David, the Uffizi Gallery, and Brunelleschi’s Dome. Staying in Florence is ideal if you love art, history, and strolling down cobblestone streets lined with cafes and boutiques.
Best for: Art lovers, first-time visitors, culture seekers
Where to stay:
Historic Center (Centro Storico): Centrally located near the Duomo, Ponte Vecchio and other major landmarks.
Oltrarno: Trendy, artisan-filled neighborhood across the Arno River with a more local feel.
Santa Maria Novella: A convenient base for train arrivals and departures.
You can stay in a luxury hotel in a restored palazzo (ancient palace), a charming boutique hotel or even a budget-friendly hostel. You’ll find everything in the Historic Center and surrounding neighborhoods.
Siena: Medieval Town Vibes and Palio Traditions
Siena is a bit smaller and quieter than Florence, but equally charming in its own way. It has a shell-shaped piazza (Piazza del Campo) that’s one of the most beautiful squares in Italy. It’s also home to beautiful Gothic cathedral and twice a year the whole town buzzes with excitement over the Palio horse race.
Staying in Siena is a great base for seeing southern Tuscany.
Best for: History buffs, romantic old town atmosphere, central for southern Tuscany
Where to stay:
Centro Storico: The historic city center within the city walls, ideal for exploring on foot.
Countryside around Siena: If you want more space, you can find villas and agriturismos with vineyards and natural surroundings.
Pisa: Much More Than the Leaning Tower
Pisa is often a stop on the “Golden Triangle” of Florence, Siena, and Pisa when travelers have a few hours and want to see the Leaning Tower. But this university city is more than just an art museum with an iconic tower. There’s a lively nightlife and university scene, Romanesque architecture, and it’s a great base for the Tuscan coast, too. It also has an international airport, making it a practical choice.
Best for: Travelers coming and going by plane, short city stays, heading to the coast
Where to stay:
Near Piazza dei Miracoli for easy access to the main sights (the tower, baptistry, and cathedral).
In the city center if you want a more local experience of Pisa (restaurants, nightlife).
Lucca: Renaissance Walled Town
Lucca is another Renaissance town but has a different vibe from Siena and Florence. It’s most famous for its ancient walls, which have survived in their entirety and which you can bike or stroll around. Inside the walls, Lucca is a maze of tiny streets, hidden squares, and Romanesque churches. It’s a quieter city than Florence or Siena, and a lovely place to unwind.
Best for: Families, slow-paced base, off-the-beaten-path charm
Where to stay: Inside or outside the city walls, depending if you want easy walking access or a bit more space. Nearby countryside has villas and agriturismos.
Best Countryside Areas to Stay in Tuscany
Tuscany’s countryside is what dreams are made of. Vineyards, cypress-lined roads, olive groves, rolling hills, and medieval hilltop towns. If you want that quintessential Tuscan vibe, then somewhere outside the main cities is a must.
Chianti: Wine Country Paradise
Between Florence and Siena lies the Chianti region, one of Tuscany’s most famous and visited areas. Famous for the Chianti Classico wine, this is where you’ll find rolling hills, vineyards, castles, and that iconic countryside look.
Staying in Chianti is ideal if you want to sip wine at sunset, eat rustic Tuscan food, and explore medieval villages.
Best for: Wine lovers, romantic getaways, couples
Top towns to base yourself in: Greve in Chianti, Castellina, Radda, Gaiole
Accommodation: Agriturismos (farm stays), vineyard villas, small boutique hotels.
Val d’Orcia: Postcard-Perfect Tuscany
Val d’Orcia might as well be a giant postcard (it was). You’ve seen those photos of Tuscany with the rolling hills, cypress trees on winding roads, and medieval villages perched on top? Chances are that was Val d’Orcia. This UNESCO World Heritage area features towns like Pienza, Montalcino, and Montepulciano.
Best for: Scenic drives, food and wine, photography
Highlights: Pecorino cheese in Pienza, Brunello di Montalcino wine, Renaissance piazza in Montepulciano, Montalcino.
Accommodation: Farmhouses, luxury countryside villas, small boutique stays.
Maremma: Wild Coast and Untamed Tuscany
Southern Tuscany’s Maremma area is a less touristy part of the region with wild beaches, Etruscan ruins, and fishing villages. It’s perfect for travelers looking to combine the Tuscan countryside charm with a seaside holiday.
Best for: Nature lovers, coastal getaways, off-season travel to avoid crowds
Top towns to base in: Grosseto, Castiglione della Pescaia, Orbetello
Accommodation: Beach resorts, countryside farmhouses, B&Bs.
Garfagnana and Lunigiana: Hidden Tuscany
North of Tuscany, bordering the Apennine mountains, you’ll find two small regions with a very different vibe: Garfagnana and Lunigiana. Both are very green, mountainous, and far less touristy than Chianti or Val d’Orcia.
Best for: Outdoor enthusiasts, adventurous travelers, peace and quiet
Accommodation: Rustic farmhouses, mountain lodges, budget guesthouses.
Unique Accommodation Options in Tuscany
Where you stay is as important in Tuscany as where you stay. In addition to Tuscan towns and villages, there are all sorts of unique accommodations to consider.
Agriturismos (Farm Stays)
Agriturismos are working farms that offer accommodation, as well as homegrown food and wine. Staying at an agriturismo lets you experience the real Tuscan lifestyle, often with meals cooked with fresh ingredients from the farm.
Best for: Families, foodies, an authentic experience
Example: An Agriturismo with its own vineyard in Chianti, where you can taste wine from the cellar.
Villas and Country Houses
Renting a villa or large country house is the ultimate Tuscan experience. Perfect for larger groups or families, you’ll often find villas have private pools, rustic kitchens, and views of the Tuscan countryside.
Best for: Groups and families, long stays
Boutique Hotels and Historic Palazzos
If you love charm but don’t want to give up modern comforts, Tuscany has many boutique hotels in historic palazzos, castles, or converted monasteries.
Best for: Couples, luxury travelers
Coastal Resorts and Seaside Stays
On the Tuscan coast, especially around the Maremma and Elba Island, you’ll find beach resorts that offer access to the sea, spas, and seafood restaurants.
Best for: Summer holidays, families with kids, beachgoers
Practical Tips for Choosing Where to Stay in Tuscany
Split your stay. Consider dividing your time between a city (Florence or Siena) and the countryside (Chianti or Val d’Orcia).
Transportation. If you’ll be relying on trains and buses to get around, it’s more convenient to stay in one of the cities. If you’re staying in the countryside, you’ll need to rent a car to get around.
Season. Summer in Tuscany is peak tourist season and also the most expensive (especially in Florence and Chianti). Spring and fall have fewer crowds, better weather, and fewer prices.
Book early. Tuscany is a popular destination and many of the best agriturismos and villas book up months in advance.
Know your budget. There’s accommodation for all budgets, from cheap B&Bs to luxury resorts. Decide what’s most important for you: location, amenities, or unique atmosphere.
Suggested Itineraries Based on Where You Stay
Florence + Chianti (5–7 days): Experience both art and culture and wine country.
Siena + Val d’Orcia (5–7 days): Perfect mix of medieval city and classic Tuscan countryside.
Pisa/Lucca + Maremma Coast (5–7 days): Leaning Tower and walled city followed by seaside escape.
Florence + Val d’Orcia + Siena (10–12 days): A well-rounded Tuscan experience.
Conclusion
Tuscany is not one destination but many: Renaissance cities, medieval villages, vineyards, rolling hills, golden valleys, hilltop towns, and seaside escapes. Your choice of where to stay will determine your experience in this magical region.
Florence immerses you in art and energy, Siena in medieval history, Chianti and Val d’Orcia are all about iconic countryside, and the coast offers wild beaches and seafood. Toss in unique accommodation like agriturismos, villas, boutique hotels, and even beach resorts and Tuscany is the perfect backdrop for your travel dreams.
By picking the right base for your travel style, or splitting your stay between a city and the countryside, you can get the best of both worlds: history, culture, cuisine, and the best landscapes in the world.
From sipping wine in a vineyard to exploring medieval alleys to gazing at Renaissance masterpieces, Tuscany has the perfect place for you to stay.
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