Looking to plan an unforgettable trip to Italy that will surely make everyone back home jealous? Why not journey to the rolling green hills and enchanting villages of Tuscany! This expansive region located just north of central Italy is the most famous in the entire country, and for good reason. With an abundance of vineyards, gorgeous architecture, and even a stunning coastline, there are plenty of things for travelers to enjoy in Tuscany.
Keep reading because this insider’s guide will help you discover the top things to do in Tuscany including the must-see sights, towns, villages, and beaches in the area. We will also suggest the best activities, tours, and experiences in Tuscany to partake in along the way so that you can make the most of your upcoming trip to Italy’s crown region!
1) Wander Through the Charming Streets of San Gimignano
You’ll feel like you have stepped back in time upon viewing the medieval towers of San Gimignano
Since Tuscany is the largest region in Italy covering nearly 8,900 square miles, you can imagine the amount of marvelous towns just waiting to be discovered within its borders. While Tuscany is known for being the birthplace of the Renaissance, this area’s history dates back much longer. San Gimignano is one of the most enchanting medieval villages within the region and is famous for its unique hill-top skyline composed of various stone towers. Though the city has been around for over 1,000 years, the character of San Gimignano has been preserved incredibly well making it a must-see stop on your journey through the Tuscan countryside.
During San Gimignano’s height of power in the middle ages, nearly 72 towers were built in the city as a display of wealth by noble families, of which, fourteen remain today. When you are not taking in the magnificent tower views of this recognized UNESCO World Heritage Site, you can wander through the endearing streets, shop in the artisan saffron shops, or enjoy a glass of Vernaccia white wine and a deliciously meal prepared fresh at a locally owned restaurant in town. If you love history and art, you are in luck, because there are also plenty of churches and museums in town to explore that are decorated beautifully in Gothic, Romanesque, and Renaissance styles. Along the way, be sure to stop at Piazza della Cisterna and Piazza Duomo, two of San Gignano’s most beloved town squares that are full of charm.
2) Tour the Vineyards & Wine Cellars of the Chianti Region
Seeing where & how the region’s famous wines are produced makes you appreciate the taste so much more!
One of the most unique aspects of Italy’s Tuscany region is that the land is incredibly well suited for farming and harvesting. With that being said, it is no wonder why Tuscan grapes are used to create some of the most well-known wines in the world! Chianti, is one of my personal favorite types of wine and is made in the area for which it is named. Located between Florence and Siena within Italy’s Tuscany region, you’ll find the gentle hills of Chianti which are home to adorable stone cottages, olive groves, and various wineries of which you can pay a visit to for cooking classes, olive oil tastings, or wine tours.
Observing the on-site location where Chianti wines are produced is a once in a lifetime experience for any self proclaimed sommelier. The best thing of all is that after you finish your tour of the vineyards and cellars, you’ll get to taste the amazing flavors of the wine and even have a chance to bring a bottle or two home! If you are staying in Florence but still want to explore the rest of what Tuscany has to offer, we recommend you join us on a Private Half Day Chianti Tour which features stops at two top-rated wineries in the Chianti Region with lunch at a Tuscan farmhouse and luxury transportation included!
3) Discover the Beauty of Siena or Attend its Famous Palio
You may be surprised by all of the amazing things that the hilltop town of Siena has to offer!
One place in Tuscany that is definitely worth visiting is the stunning city of Siena which just happens to host one of the biggest events in Tuscany each year. If you love excitement and want to partake in an unforgettable cultural experience, consider attending the Palio di Siena which takes place in July and August in the town’s main square, Piazza del Campo. This series of bareback horse races is an age old tradition that sparks a fun yet competitive spirit between the various neighborhoods of Siena. As each district roots for their jockey to bring glory and victory home by winning the race, there are plentiful open air feasts and even dancing out on the streets to celebrate the festivities. Even when it is not Palio season, you can see the vast cultural importance that this event brings to the city.
While the town gets busy during the summer months because of the famous Palio, Siena is relatively quiet throughout the rest of the year. In my opinion, this is a fantastic time to visit Siena because accommodation prices are low and you won’t find nearly as many tourists as in some of the bigger cities Italy. Thankfully, this city is a hub for art and culture so you’ll have plenty of things to do to keep you entertained during your stay. For example, Siena’s Cathedral, also known as the Duomo di Siena, is one of the most breathtaking in Italy and features an ornate interior decorated with alternating slabs of black and white marble. Some of the other main attractions in town include the beautiful Pubblico Palace, Tower of Mangia, and the Basilica of San Domenico where the head of Saint Catherine, one the patron saints of Italy, is preserved as a relic.
There is much more to do in Siena where that came from too, so definitely be sure to pay this incredible city a visit on your grand tour of Tuscany! If you are staying in Florence, you may want to join us for a Private Siena and San Gimignano Day Trip where you will visit both Siena and San Gimignano while enjoying wine tastings and local cuisine along the way!
4) Take in the Spectacular Views from the Top of the Florence Duomo
A trip to Tuscany would not be complete without seeing the region’s largest city, Florence!
You have probably heard us rave about Florence in many of our other blogs and that is simply because it is an amazing city, not to mention the capital of Tuscany! With a vast history, large population, an abundance of tourist attractions, and tons of things to do, Florence is a great starting point for Tuscany first-timers. Upon arrival, one of the first things you’ll notice is the towering Duomo of the Cathedral of Santa Maria del Fiore. This magnificent church with a intricate marble exterior took centuries to build and was completed during the Renaissance era with Brunelleschi’s iconic dome, of which, you can climb up today for fantastic views of the city!
When you are not taking in the main sights of the city such as the fantastic Duomo Complex, Ponte Vecchio, or Piazza della Signoria, you can visit Florence’s world-renowned museums. My personal favorite is the Uffizi Gallery which features textbook-worthy masterpieces by the likes of master artists such as Botticelli, Raphael, Leonardo di Vinci, and more! Another must-see museum in the historic center is the Accademia Gallery, where Michelangelo’s David is located. This towering marble sculpture is one of the most beloved works from the Renaissance and will surely take your breath away.
5) Taste the Region’s Local Wines & Organic Cuisine
After you have seen where the grapes are grown and the wine is stored, you have to try a glass for yourself!
Let’s be honest, your visit in Tuscany wouldn’t be complete without trying a glass of locally produced wine! Whether or not you choose to take part in winery tours of Tuscany’s many cellars and vineyards, you can still enjoy the region’s most prized specialty. No matter what town in Tuscany you happen to be in, you’ll find fantastic wines on every restaurant or bar menu and in any market you come across. Wondering just what wines you have to try out during your trip to Tuscany? My personal favorites grown in the region include Brunello di Montalcino, Carmignano, Vernaccia di San Gimignano and of course, Chianti Classico.
There is no better way to drink wine in Tuscany than by pairing it with the local cuisine! For an afternoon or before-dinner snack, go for a tagliere board. These scrumptious Italian charcuterie plates include a mix match of tasty cheeses, jams, and cured meats. If you are in the mood for something more filling, go for a steak or homemade pasta! Each town in Tuscany has their own typical specialities however, so we recommend you ask your server for suggestions when ordering. For example, the city of Siena is well known for its thick pici pasta, while San Gimignano serves up a delicious leek and ham soup seasoned with locally grown saffron. If you are headed to Florence, be sure to check out our post covering the must-try foods of Florence!
6) Take a Photo With the Leaning Tower of Pisa
You’ve probably seen it many times in pictures, but seeing the leaning tower in person takes the cake!
When you think of postcards from Italy, there is a good chance you think of the Leaning Tower of Pisa and yes, you guessed it- it is located in Tuscany! This free standing bell tower, also known as a campanile, was completed in the 14th century and is famous for its nearly forty degree lean. The tower first started leaning upon construction in the 12th century due to the soft texture of the ground below, but has since been stabilized despite its seemingly bizarre lean. Today, you can pay a small fee to enter the complex, join a sightseeing tour, and even have your chance to take a funny photo of you trying to push the tower upright- but don’t expect this tower to actually be moved anytime soon!
The greater Pisa Complex which earned the title of a UNESCO World Heritage Site, includes a Cathedral, Baptistry, and a Monumental Cemetery that feature amazing examples of medieval artwork and architecture. While the Pisa Complex is definitely the most visited part of the commune, there are plenty of other things to do and see in the greater city as well such as visiting the local churches, shopping at the plentiful artisan boutiques, or enjoying a typical Tuscan meal at a picturesque cafe. With that being said, be sure to hang around and explore Pisa for a bit after your visit to the iconic leaning tower.
7) Road Trip Through the Countryside & Stop at the Breathtaking Towns Along the Way
Renting a car can be a great way to discover the stunning landscape of Tuscany!
Besides the Tuscan cities, towns, and villages already mentioned in this post, there are plenty of others that are worth taking a trip to see such as Lucca, Montepulciano, Cortona, Barga, and Pitigliano- just to name a few. While there are buses and trains to get from one point to another in Tuscany, reaching smaller towns and villages can be difficult. So, if you have the drive to get out on the open road, renting a car may be a great option for you!
The flexibility of being able to stop wherever you please with your own car is a major bonus. For example, if you see an adorable winery on the side of the road, simply stop and check it out. Want to explore Tuscany on your own without a map? Opt to get lost on the gorgeous winding back roads instead! If you do choose to go this route, be sure you obtain an International Driver’s License beforehand and consider the costs of gas and tolls as discussed in our recent blog post about the Best Ways to Travel in Italy.
8) Take in Spectacular Views Along the Tuscan Coastline
Most people don’t realize that the region of Tuscany is home to a breathtaking coastline full of must-see beaches
When people think of Tuscany, they usually think of the hills and vineyards- not the coast! But the truth is that there are some stunning beaches in the region that can make for a perfect day trip outing on a warm day. Located along the west coast of Italy, the region of Tuscany hugs the Ligurian and Tyrrhenian seas. While the northern coast of Tuscany features luxurious beach resorts and spas, the southern area of Maremma boasts breathtaking natural reserves along with the clearest waters and best beaches for swimming. The central Etruscan Coast also has a stunning shoreline complete with charming seaside villages and a variety of beaches to choose from.
Did you know that the region of Tuscany is also home to various Islands just off the coast? The largest of the Tuscan islands, Elba, is a popular vacation destination among Italians and is well known for its colorful towns, turquoise waters, coral reefs, and amazing mountain ranges. This nature lovers’ paradise can be easily reached by ferry from the coastal town of Piombino. Other notable islands in the Tuscan Archipelago located between the Ligurian Sea and Tyrrhenian Sea are Giglio Island and Giannutri Island, both of which offer a quiet escape in a pristine natural setting.
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Thanks for reading our insider’s guide to the best things to do in Tuscany, Italy! We hope that you will find it helpful while planning your trip. Besides offering Tours in Florence and Tuscany, we also offer top rated experiences in various cities across the rest of Italy! For more information or to arrange a tour, check out What a Life Tours or contact us by phone +39 06 88975757/+39 334 7273299 (WhatsApp), or email at firstname.lastname@example.org!
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