Insider’s Guide to Tuscany – The 10 Best Things To Do

From world-class wining and dining to rolling hills and dramatic religious architecture, Tuscany is one of the most popular destinations in the world to visit. With plenty of living history and passion baked into everything, it’s no wonder why.

However, because it’s so incredible, it can be hard to narrow things down to a feasible itinerary. Allow us to do the hard part for you, with our insider’s guide to Tuscany. All you have to do is reap the rewards! See all of our Italy travel guides.

Best Places to Visit in Tuscany


We have to start off with Florence, or “Firenze” in Italian. Known as the actual birthplace of the Renaissance, it’s no secret that it’s filled with mind-blowing museums and art galleries. However, beyond the arts, it has also been a very important hub of politics and culture for centuries.

As the capital of Tuscany, you can expect a quintessentially romantic experience, no matter where you go.

San Lorenzo Market

If you or someone you love is into high-end clothing, accessories, or leather in general, stop at San Lorenzo for some serious treasures. During the Renaissance, Florence was known around Europe for its high-end leatherwork.

That tradition is still alive and well, and you can score some beautiful gloves, shoes, or jackets for a surprisingly affordable price in this open air market.


Did you know that there is actually a term for the potential dizziness you may experience after viewing the extensive amount of masterpieces around Firenze?

It’s true! “Stendhal Syndrome” is named after the renowned French artist of the same name who experienced this when visiting the capital, himself. Hold onto something stable, because these museums are out of this world:

Palazzo Vecchio

Once housing the government, Palazzo Vecchio now houses incredible works of art. The courtyard alone shows off a comprehensive array of stuccoes and frescoes. The ground floor is the biggest and was originally decorated by Michelangelo and Leonardo. The second floor once held the Medici family’s rooms.

Galleria dell’Accademia

The star of the show at the Accademia is Michelangelo’s “David”, however, there are many other incredible artworks by him and Giotto, Perugino, Pontormo, and many more. As it is a smaller museum, you really only need 30 minutes to an hour to get through it.

Uffizi Gallery

As the oldest museum in the world (and one of the most famous), the Uffizi Gallery is simply unparalleled in its collection of Renaissance-era artwork. Not to mention, the beautiful building itself was around during the 16th-century!

Inside you have everything from Botticelli’s ‘Birth of Venus’ and Caravaggio’s ‘Medusa’ to da Vinci’s ‘Annunciation’. Going back from the Middle Ages to the Modern period, you’re sure to enjoy yourself with a guided Uffizi gallery tour.

Things to do in Tuscany

Wine Tours

Tuscany is one of the most prolific wine regions in the entire world, but is best known for its Chianti, Brunello di Montalcino, and Vino Nobile di Montepulciano. Their history of wine-making dates back all the way to the 8th-century BC, making it one of their longest-standing traditions. Needless to say, Tuscans take wine pretty seriously!

While you could definitely get some great wine at most restaurants in Florence, you want an authentic Tuscan experience don’t you? Imagine arriving at a centuries-old villa surrounded by acres of vineyards, feeling the fresh countryside breeze blow through your hair.

You’re invited in by the owner for a private wine tasting along with a guide and winemaker to share expert tips and history on each one. You can have all that and more with Florence wine tasting tours we’ve carefully curated for you!

Tuscany Winery

Vespa Tours

Isn’t the most Italian form of transportation the Vespa?! You simply haven’t visited Tuscany until you’ve zipped around on one of these nearly 80-year-old style icons! However, you’re probably best off going with a guide who can lead you through the safest routes.

Better yet, why not check out a Tuscany Vespa tour? These tours each have their own specialty: from a focus on wine, to traditional cuisine, to architecture. No matter what your interests are, you’re sure to find something you love.

If you don’t feel comfortable being the one in the driver’s seat, there are also double-seater Vespas so you can ride with a partner.

Visit Vincigliata Castle

This medieval beauty stands looming on the top of a rocky hill very close to Florence (note: it  does offer amazing views of the city, as it’s just 20 minutes away). It’s so beautiful, in fact, that many people get married here!

While the 13th-century castle started out as a stronghold of Florentine nobility, it ended up serving as a POW camp in the 1940s and housed various important British officers. Today, it has a much happier atmosphere with its own vineyard.

Take a Cooking Class

What if we told you that you could take authentic Tuscan cuisine with you back home and have it whenever you want? No, we’re not talking about taking some pasta home with you and freezing it.

Rather, you can take a Tuscany cooking class and learn the skills to make you and your loved ones a delicious, authentic Italian dish any time!

They’re all different, so why not take a couple? Some are in countryside farmhouses, while others are in elegant villas. It’s not uncommon for the classes to take place in the chef’s own homes, displaying exactly what Italian hospitality really is.

These classes teach you techniques that have been passed down from many generations, from homemade pasta to bruschetta, and even Tiramisu!

Go Out to Eat

Tuscany is known as one of the biggest foodie cities in the world. They don’t rely on newfangled techniques or trends, either. They do what they know best, and what their ancestors knew best.

Il Santo Bevitore has been around for over 20 years, delivering creative Tuscan dishes like handmade pasta, specialty breads (try the focaccia!), and plenty of small-batch Tuscan vintages to accompany it.

Osteria I Buongustai sits right in the heart of the city center, and features a group, table-sharing setting. Their spaghetti alla carbonara is one of the best we’ve had the good fortune of trying.

Trattoria Mario is a family-run joint and has been serving up their signature T-bone steaks for 70 years now. Needless to say, they’ve had plenty of time to perfect their meats.

Melaleuca can’t be forgotten, though it is a bit less traditional than the others. Still, if you’re vegetarian or vegan, you’ll appreciate this bunch-lunch bistro. It’s one of the best brunch spots, complete with artisan-roasted coffee.


As kids, we all knew it as “The Leaning Tower of Pizza”, and while you can definitely get a good pizza pie in Pisa, the tower is not quite made of it. However, it does really lean!

We should mention though, the leaning tower is just one small aspect of this beautiful city full of impressive architecture and natural landscapes. Let’s check out the top activities to do in Pisa!

leaning tower of pisa

Leaning Tower of Pisa

Let’s start things off with the most obvious (and one of the most fun!). There are plenty of Tower of Pisa tours that include skip-the-line tickets so you can head straight inside and head up the spiral staircases! Learn about the crazy history behind the mostly-marble structure, including how Galileo used it for testing!

Cathedral of Santa Maria Assunta

This almost 1000-year-old cathedral is simply amazing, with fantastic stone and marble arches sealed off by 3 luxe bronze doors. The interior is perhaps just as magnificent, with a Romanesque style complete with a gold ceiling and frescoed basilica. Undoubtedly, it’s one of the most beautiful churches in all of Tuscany

The Baptistery

Also located in the legendary Piazza dei Miracoli, the Baptistery is gorgeous inside and out. Interestingly enough, it took so long that you can see the transition from Romanesque style on the bottom, to Gothic style on the top. Its round shape is quite unique, and is actually the largest baptistery in the entire country. Fun fact: it also tilts (just not as much as the tower)!

Campo Santo

Situated just to the side of the cathedral, Campo Santo is also made of the same stone as the other amazing structures in this square. The courtyard is relaxing and a wonderful place to take a stroll while admiring the artistry that went into this place. The interior hallway shows off natural lighting along with many important frescoes.

Chianti and Siena  

Situated right in the center of Tuscany, Chianti is known for its rolling hills, old fortresses, country villas, and of course – its wine. We can confidently say that even if you aren’t a huge wine fan, you’ll enjoy going on guided Chianti wine tour! With these handpicked excursions, you get to dive deep into wine tasting and learn how to make the Chianti, named for the region, itself.

We understand that there is more to Chianti than just wine (although you’d be remiss to forget it entirely). If you’d like to see a bit more, you’ll probably be best off doing a day trip from Florence. Not only will you learn about wine but get to see some more architecture and cuisine from the region.

These tours usually last all day, starting off early in the morning. Your transportation is all taken care of, and most tours pass through for tastings in Chianti/Siena/San Gimignano. Don’t forget to try their world-famous gelato in the tower of San Gimignano!

These are fantastic ways to escape the busy, noisy city centers and relax with the finer things in life.

Siena in Tuscany

Visit Castles

Who doesn’t love a good ole’ visit to a castle? Especially if you’re coming from the US, visiting castles is something you may not get to do every day. Tuscany has various Middle-Age and Renaissance-era castles, though most aren’t located in a main city.

For example, you can find the Castello Banfi in Montalcino near Siena, Castello di Vicchiomaggio right in the heart of Chianti, or the Aghinolfi Castle in Montignoso.

Duomo di Siena

This medieval church was built in the 1200s, creating the form of a Latin cross, along with an iconic dome and rising bell tower. Both the exterior and interior are made of very uniquely-colored marble: white, dark green, and red!

The façade is also intriguing, with elements of French Gothic, Romanesque, and Classic architecture. You’ll notice gargoyles and saints, prophets, philosophers, apostles, and many other Gothic-style statues on the exterior, which are reminiscent of Paris’ Notre Dame.

If you want to see one of the most gorgeous, intricate floors, make sure to go inside. The inlaid marble mosaic flooring is comprised of 56 different-sized panels made by around 40 different artists!

Look up and you’ll find various masterpieces by Bernini, Michelangelo, Simone Martini, and Lippo Memmi. It may not be the Uffizi, but this church has some seriously awe-inspiring sculptures and paintings. Make sure to check out the Piccolomini Library inside, too!

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