As someone enjoying the splendor of Tuscany, I am blown away by all of the stunning options when it comes to the best places to stay. A nice weekend trip (or even a longer weekend) is my favorite way to travel to soak up all of the details of one place. From Tuscany’s stunning medieval hilltop towns to wine tour getaways, I can’t get enough of the many, many travel experiences Tuscany has to offer. Each region is full of its own culinary and artisanal specialties, and in my lifetime I hope to experience as many of them as I can.
If you’re currently in the position of needing to choose where to go and what to do, it might be an overwhelming prospect with all of the options available to you. We know that when you are planning your trip to Italy, you only want to stay in the best places that Tuscany has to offer.
To help you with the decision-making process, continue below to access sample categories of trips as well as individual towns and what to do in each one.
How to Get to Tuscany
Getting to Tuscany is easy. There are two airports, the Galileo Galilei International Airport in Pisa and Amerigo Vespucci Airport (also known as Peretola) in Florence. From either of those cities, continue your journey by train or rent a car to reach your other destinations in Tuscany.
The 4 Best Places to Stay in Tuscany (Without a Car)
Florence is known for being the birthplace of the Italian language, a hotspot of the Renaissance, and the home of the extremely influential Medici family. It’s also the top place to stay in Tuscany, with countless museums, delicious food, and great shopping. Walk through one of Florence’s many gardens, like the Boboli Gardens, or visit Casa Buonarotti, the childhood home of Michelangelo. Shop for leather at the Scuola del Cuoio, a renovated church.
Insider Tip: Visit one of the many markets to try local specialties and shop for culinary souvenirs. The Mercato Centrale serves hot food and has an entire level dedicated to fresh meat, fish, produce, specialty pastas, wine, and more.
In Siena, one of Italy’s most beautiful medieval villages, you will find a great number of things to do, making it an ideal place to stay in Tuscany. Start your itinerary by getting a coffee and pastry at Nanninni, one of Siena’s classic stops. Then visit the cathedral, Palazzo Pubblico/Piazza del Campo, and the Torre di Mangia. Eat pici, a local pasta specialty, and have ricciarelli, a typical Senese cookie, while you are there.
Insider Tip: Research the dates for one of Italy’s oldest (and most important) horse races, the Palio. It takes place twice every summer, in July and August, and is not to be missed.
Pisa is always high on visitors’ lists as one of the best places to stay in Tuscany. Seeing the Leaning Tower in-person is a must-do, but the Duomo, baptistery, Palazzo Blu gallery and more also rank high among the options of other activities.
Insider Tip: For five euro, purchase a ticket to walk along the city walls. You’ll avoid the crowds in the Piazza dei Miracoli and have a unique vantage point of the city!
Calling all Flea Market Flip fans. If you visit Arezzo on the first weekend of the month, they have a town-wide flea market, with hundreds of vendors selling vintage and antique items. It’s your chance to score a unique souvenir. From small trinkets to saucers, clothing, jewelry, art and even furniture, there is something here for everyone! Make sure there is room in your luggage.
Insider Tip: Visit Arezzo on the first weekend of the month, when the town hosts the largest and oldest antiques fair in Italy, with hundreds of vendors selling vintage and antique items. It’s your chance to score a unique souvenir. From small trinkets to saucers, clothing, jewelry, art and even furniture, there is something here for everyone!
The 4 Best Places to Stay in the Tuscan Countryside
5. Greve in Chianti
Because no trip to Italy would be complete without a bit of vino, put your taste buds to the test in Greve in Chianti. Only a short stop between Florence and Siena, it provides visitors the chance to bike through vineyards, go to the wine museum, or visit the Verrazzano Castle.
Insider Tip: Chianti is one of the most famous wines in the world. Consider making plans to go and see how the process works, and purchase a few bottles to bring home with you.
If you want to feel like a royal, visit Montepulciano, another one of the best places to stay in the Tuscan countryside. Journey back in time through its medieval streets, pop into some of the town’s meat and cheese shops for local specialties, or visit one of the famous palaces, like Palazzo Tarugi and Palazzo Comunale, for a slice of local history. A glass of Vino Nobile di Montepulciano DOCG is almost obligatory, known for its deep and complex flavor.
Insider Tip: Climb to the top of the bell tower, the highest point in Montepulciano, for stunning views of the town and its surroundings.
7. San Quirico d’Orcia
If you’ve never heard of San Quirico d’Orcia, you’re not alone. Most tourists overlook this charming medieval town in the Val d’Orcia. But, don’t make that mistake when you look for the best places to stay in Tuscany! It is sure to be a relaxing and restorative part of your trip, away from the huge tourist crowds. Explore the historic town center, Horti Leonini, a beautiful public Renaissance garden, and Chapel Vitaleta.
Insider Tip: For film buffs, San Quirico d’Orcia is where they filmed iconic scenes in Gladiator. Visit the Gladiator Photo Spot, which is located right outside of the city walls. There’s no better place to take photos of the iconic cypress trees and rolling hills.
Volterra is rich in its artistic and religious history and a gem for those looking to step into a town that isn’t overrun with tourism. From learning about the town’s production of alabaster to visiting more well-known sites like the Etruscan Museum, Baptistery of San Giovanni, Cathedral of Santa Maria Assunta and more, you will be sure to enjoy this top place to stay in the Tuscan countryside.
Insider Tip: If you are looking to get the most out of your itinerary, purchase the Volterra Pass to gain access to the Palazzo dei Priori, Pinacoteca, Museo Etrusco Guarnacci (Etruscan museum), and Roman theater.
The 4 Best Places to Stay in Tuscany Wine Country
From its delicious Brunello wine to the intrigue and energy of the narrow city alleyways, Montalcino is one of the best places to stay in Tuscany wine country. The town still has its protective fortress and castle, making you feel like you’ve successfully time-traveled through history.
Insider Tip: If you plan to visit in July, don’t miss the town’s annual Jazz & Wine Festival.
10. Castellina in Chianti
Foodies and wine enthusiasts, rejoice–in Castellina in Chianti, you’ll be staying in one of the best places to stay in Tuscany! Truly a hidden gem, you’ll feel like you’re going back to the Middle Ages when you walk along its streets. Visit the Rocca Fortress, archeological museum, and Church of San Salvatore, then take a break and enjoy those Sangiovese grapes.
Insider Tip: Stroll through Via delle Valle (a medieval tunnel) for a unique shopping opportunity or to enjoy the view from the small wall openings.
Here, a “small town” means that just 100 people live in the small village of Bolgheri, another gem of Tuscany’s wine country. Don’t underestimate its potential–this gem has amazing cuisine and wine (in fact, some are called Super Tuscan). Spend time in wine tastings, visiting the Viale dei Cipressi, and more.
Insider Tip: Bolgheri is part of the Etruscan Coast, stretching from Livorno to Piombino. Stop for a swim, read a book on the beach, or visit one of the many medieval villages like Populonia or Suvereto.
12. Gaiole in Chianti
If you are looking for a special addition to your trip, stay in Gaiole in Chianti, the heart of Tuscan wine country. Tourists from all across the world visit to soak up the experience of its vineyards, wine, and beauty of the area. Its historical center, Church of San Gigismondo, and Ricasoli Square are must-dos, as well as Castello di Brolio and Meleto Castle.
Insider Tip: Add some pizzazz to your wine tasting by experiencing it in a castle. The Ricasoli family has been making wines from the vineyards surrounding their estate, Castello di Brolio, since 1141!
The 4 Best Family Places to Stay in Tuscany
13. San Gimignano
San Gimignano is another charming medieval town that is worth factoring into your plans for the best places to stay in Tuscany. Walk through the winding streets and climb the Torre Grossa.
Insider Tip: Everyone knows that no trip to Italy would be complete without one (or multiple) scoop of gelato. San Gimignano has a gelateria known for its many awards and championships, Gelateria Dondoli, that is worth a visit!
Did you know that Pienza is an ideal town? Years ago, Pope Pius II created an urban oasis that makes it one of the best places for families to stay in Tuscany. Take in the sights of centrally-located Piazza Pio II, or visit Piccolomini Palace, Pope Pius II’s former summer residence. Other beautiful places to visit include the Chapel Vitaleta and the Church of the San Biagio.
Insider Tip: Did you know that Pienza has its own cheese? Try some Pecorino di Pienza!
If you are looking for a unique and memorable addition to your stay in Tuscany, don’t miss the Saturnia hot springs. When the hotel pool just won’t do, family members of all ages will enjoy a relaxing and restorative dip in these famous waters. Then, venture out and explore everything that Maremma has to offer.
Insider Tip: The Cascate del Mulino (the picturesque hot springs) are almost never as empty as they look on social media. Go during the week, or during spring or winter, to avoid the many crowds.
You can’t get more “traditionally Tuscan” than Cortona, as the town is well-known for being the inspiration behind Frances Mayes’ book, Under the Tuscan Sun. It is one of the best places to stay in Tuscany for good reason: it packs a punch for being a small hilltop town. Visit the Etruscan Museum, where you will find a variety of bronze and ceramic items; the Fortress of Girifalco, or the Convento di San Francesco.
Insider Tip: Seek out the Belvedere di Cetona at sunset for a breathtaking, panoramic view.
The Best Luxury Villas in Tuscany for Your Stay
Luxury Hotel in Tuscany without a Car
No car? No problem! Hotel La Gemma in Florence is sure to impress during your stay. Located right in the heart of the Tuscan capital, you are a short walk from the Santa Maria Novella train station and all of the other stunning attractions. Let the property’s rich decor and many amenities spoil and inspire you.
Luxury Villa in the Tuscan Countryside
If you are looking to be “wowed” by historic buildings, high, domed ceilings, and stunning views, look no further than Precise Tale Poggio Alla Sala. This hotel is perfect for those who appreciate historic details as well as modern luxuries. It has a pool, sauna, spa and wellness center, and guests have been impressed by the gorgeous views and surroundings, too.
Luxury Villa in the Wine Region
If you are looking to celebrate a special occasion or just stay in the lap of Tuscan luxury, the Castello di Velona is hard to beat. Named one of the leading hotels in the world, it is an ideal location for guests to enjoy views overlooking the Val D’Orcia and Tuscan vineyards while offering a restaurant and spa.
Luxury Hotel for Families
At the Agriturismo Bio Aia Della Colonna, enjoy what guests call an idyllic location, nestled in the Tuscan hills less than 10 miles from Saturnia. Guests can enjoy the Morellini di Scansano wine that is produced on-site, meals on the terrace, and easy access to some of the area’s most picturesque medieval villages.
No matter your ideal budget, setting, or location, you are sure to find a wide range of the best places to stay in Tuscany. Spend some time in the region to discover everything it has to offer.