Tuscany is one of the most beautiful regions in Italy and it’s visited by thousands of people each year. The thing about Tuscany is that it’s pretty massive and full of absolutely incredible cities and towns to visit. In fact, planning a trip to the Tuscan countryside can get a bit overwhelming, especially when trying to decide the best location to stay. The truth is that this part of Italy has tons of great places to stay, but it all depends on what you’re looking for. We’ve come up with a list of some of Tuscany’s best spots in order to help you with your plans. Here’s what we suggest:


Florence tops our list as it’s the largest city in Tuscany and has plenty to keep you busy. When choosing a base, you’ll want to pick somewhere that offers plenty of amenities, accommodation options, and food choices. Florence has all of that and more! Plus, it makes Tuscany’s other destinations much easier to reach. If you’re traveling without a car, Florence is an ideal base as it is well connected to the rest of Tuscany by bus and train. While in Florence, make sure to visit the Uffizi Gallery to see the immense collection of artworks from the Renaissance era. Stop by the Accademia to see Michelangelo’s David statue, and spend time exploring the architecture in the city center. In fact, this part of Florence has been labeled a World UNESCO Heritage Site, so expect lots of beauty, history, and culture. Other highlights include the Ponte Vecchio, the Duomo, San Lorenzo Market, and Piazza Della Signoria. Florence is also widely known as a foodie city so make sure to try out as many restaurants as possible. Making this city your Tuscan base is the best way to ensure you’ll stick around long enough to taste test as many dishes as possible. Pasta, pizza, and gelato are staples (of course) so try as much of those as you can.

places to stay florence


Pisa is a medium-sized city that is much less crowded and bustling than Florence. It’s a great base in Tuscany as it’s well connected by public transit. It’s not exactly people’s first choice as a base, but for those who like a more laid back atmosphere, it’s a great option. Pisa is a university town, and moves at a much slower pace than other cities. While most travelers want to see the Leaning Tower of Pisa, many of them do it on a quick day trip. If you want to be able to take your time and see the tower both at night and during the day, spending a few nights is great. When you aren’t photographing the tower make sure check out the River Arno, the Duomo di Pisa, Camposanto, the Baptistery, and Corso Italia, where you can do some shopping.


Lucca is an excellent Tuscan base, especially if you’re a family traveling with children. It’s pretty small and manageable to get around, but still has lots to do and plenty of amenities. It’s a friendly city, has a good amount of green space, and isn’t overrun by tourists (yet.) Lucca is also relatively close to a few different small towns and the coast so you have access to other noteworthy places in Tuscany. This city is often busy with daytrippers, so staying for a few nights will help you beat the crowds. Make sure to spend some time walking or biking the city wall. It’s Lucca’s main highlight as it’s 80 feet wide and 2.5 miles long. You’ll get fantastic views and access to the picnic areas, green spaces, and cafes that line the top of the wall. The city is also known for its historic churches so make sure to check those out too. Other highlights in Lucca include the Duomo di Lucca, San Michele in Foro, Piazza dell’Anfiteatro, and the opera.

San Gimignano

This town may be small, but it’s definitely worth a stay if you want to experience authentic, Tuscan life. It was once the home of wealthy Tuscans, who built grand towers to signify their wealth. At one point in time there were 75 of them, but now only 13 remain. These towers offer great views if you’re willing to make the climb. Don’t forget to check out the historic downtown area which has been declared a World UNESCO Heritage Site. Some of the city’s main highlights include the Piazza del Cisterna, Piazza del Duomo, Salvucci twin towers, and the City Hall tower. A night or two is a perfect way to soak up the history and culture without feeling rushed. After a hearty day of sightseeing, test out the different restaurants to taste local dishes. Don’t forget to try a glass of Vernaccia di San Gimignano, one of Tuscany’s most famous white wines.


The Chianti wine region of Tuscany is probably one of the most famous areas for tourists. Wine lovers need to visit because there are hills and hills of beautiful vineyards, wineries, and opportunities to taste Chianti of course. This is a great place to spend a few days and nights, especially in a quaint and charming bed and breakfast. Find accommodation in a hilltop village where you can relax, sip wine, and watch the sunset over the endless, rolling hills. Make wine tasting a top priority, going to as many wineries as possible. Chianti also has a sculpture garden, historic castles, churches, and museums. This is the perfect destination to rent a bike and take your time leisurely wandering the region to see the sites, natural beauty, and try the wine. It’s also a great place to get tipsy, eat as much food as you want, and laze around without a care. You’ll definitely want to stay a while, and you may never want to leave.

chianti italy


Siena is one of the larger cities in Tuscany, making it a perfect spot to use as a base when traveling. There are plenty of hotels, restaurants, and things to do here. And, it’s well connected to public transit so you can get around quite easily both within the city and beyond. Siena was first settled by the Etruscans, so you can expect lots of interesting architecture and history here. Take your time seeing and experiencing everything this beautiful city has to offer. Some of the highlights include the Cathedral of Santa Maria Assunta, the Piazza del Campo, and the Palazzo Pubblico. Make sure to visit the Biblioteca Piccolomini for the impressive paintings, the Siena National Gallery for impressive works of art, and the Porta Pispini to learn all about history. The Siena Civic Museum is a great spot to visit on a rainy day, and the bar, Un Tubo, is the perfect place catch a live jazz show.


If you want to experience what real, Tuscan life is like, stay a while in Volterra. It’s a charming, medieval town that is small but full of interesting architecture and culture. The city wall offers incredible views of the surrounding landscape and the city, making it a great stop for photographers. Highlights here include the Palazzolo dei Priori, Museum Civico, Pinacoteca, and the Baptistery. You’ll also want to stop off and visit the Roman remains like the theater and the Medicean Fortress. If you really like history, spend some time wandering around the Etruscan acropolis, the archeological sites, and the fortress.


This city may be small but it packs in the culture and natural beauty. You can find it atop the Tuscan hills, boasting incredible views of the vineyards and rolling hills. Just outside of Florence, Arezzo is great for a day trip. However, if you enjoy a slower pace of life, smaller cities, and lots of nature, you may want to use Arezzo as your base for visiting Florence instead. It’s a wonderful city to view Florentine architecture, and has great markets to explore during the summer months. Make sure to spend some time people watching in the Piazza Grande, explore the historic fort from the 16th and 17th centuries, and stop by the Duomo San Donato. Go to see a show at the luxurious Teatro Petrarca, gain some knowledge at the Museo Archeologico Mecenate, and tour the Basilica of San Francesco. If you’re into art, the Museum of Medieval and Modern Art is a must-see, as is the Casa del Vasari. Spend some time wandering the parks, exploring the antique market, and enjoying a walk by the lake.

arezzo italy

Crete Senesi

This area of Tuscany has been described as looking like another world. It’s surrounded by gray, clay-like hills and the remains of a once vibrant sea. The area is flooded with history and dotted with ancient towns and medieval settlements. The region is located south of Siena and is one of the most unique landscapes in all of Tuscany. One of the best ways to explore this area is by car, so try and rent one if you have the chance. There are several small towns that make great stopping off points so it might be worthwhile to explore them before choosing a base. Some noteworthy towns include Asciano, which is scattered with churches and a Etruscan settlement. Check out San Giovanni d’Asso, a tiny settlement with an interesting museum dedicated to truffles. There’s the medieval hamlet of Lucignano d’Arbia, and Monte Oliveto Maggiore Abbey, which is a Benedictine Monastery. While staying in Crete Senesi, make sure to try some of the local foods like truffle mushrooms, pecorino cheese, and honey. 

Val d’Orcia

This region of southern Tuscany is exactly what you probably pictured when thinking of the Tuscan landscape. It’s made up of endless rolling hills, farms, vineyards, and lots of natural beauty. It’s postcard perfect and is honestly worth a stay, at least for a night or two. Visitors will be met with views of hilltop towns, medieval settlements, cypress trees, vineyards, and golden fields of wheat. The entire area is considered a World UNESCO Heritage Site and a nature preserve, which means it’s kept in pristine condition. This landscape has been the focus of many Renaissance painters who found its beauty too magnificent to ignore. Visitors will be sure to stumble upon castles, small villages, hamlets, and abbeys. Make sure to try the local wine selections, especially Bruncello di Montalcino and Vino Nobile di Montepulciano. The local foods are worth trying as well so make sure to taste the pecorino cheese, truffles, chestnuts, and mushrooms. There are tons of small towns and villages in this region so you can take your pick when looking for a place to spend the night. Many stay in Siena and visit this area on a day trip. However, there is so much to see that we recommend actually spending a night here to fully appreciate the beauty and culture.


This small city makes a perfect base for those who want a natural getaway someplace other than a city. It’s surrounded by natural beauty, rolling hills, and plenty of farms. The locals take their produce and cuisine seriously so expect lots of great restaurants, delicious food, and great wine. In fact, you’ll probably come across a ton of fantastic restaurants that offer farm-to-table options. Don’t forget to try the handmade pasta (it’s famous here!) Visitors will be met with olive groves, historic buildings, and lush forests that surround the city. If you want to experience authentic, Tuscan life and culture, a night or two in Montaione is just perfect for you.

If you’re visiting Tuscany, make sure to choose a great base to stay. The region has so much to see and do that you’ll need a comfortable starting point from which you can explore. Whether you prefer big cities with lots of amenities or small towns with authentic charm, you’ll be able to find something in Tuscany that’s best for you. Bring your family, your romantic partner, or just a friend-as long as you’re with someone you love, you’ll have an unforgettable time in Tuscany.