Discover the Best Places to Visit in Tuscany

If you’ve considered driving in any region around the world, Tuscany should sit at the very top of your list. For context, Tuscany is a region in central Italy. It is divided into 10 provinces and covers nearly 9,000 square miles. The most well known of those provinces are Florence (Firenze) and Siena. It’s sometimes considered Italy’s most timeless region. If you are curious why you should set your travel sights on Tuscany, look no further than the historic towns, world-class art, and delectable cuisine. There are many places that you will visit in Tuscany that will simply leave you breathless. I’ve made multiple trips to the region and just can’t get enough.

In all fairness, I did not rent a car on my first visit to Tuscany. But that quickly changed over the years and now I can say that having a car is a game changer for a Tuscan adventure. Imagine driving through the countryside with top down and smooth tunes flowing from the speakers as the slight scent of grapes permeate the air. Ok, I didn’t have a convertible for my adventure but having a car provided access to places that otherwise would have been difficult to explore. In this blog, I’ll share insight to some of my favorite towns and experiences from my trips to Tuscany. I’ll also highlight some of the most famous landmarks and dive into the must make stops in this incredible wine region.

The Art and Architecture of Florence

Florence is the capital of Tuscany and home to some of the most important art of the Renaissance. If you need to make a base in the region, this is where you want to do it. But I’d recommend touring this city without a car. While you may pick up your rental car here for the rest of your journey, don’t think about driving in Florence. The streets are super narrow and it is primarily a pedestrian city. Many streets are blocked to motor vehicles making driving around in the city challenging. It’s not impossible but it can be very stressful.

Ponte Vecchio bridge
The Fountain of Neptune in the Piazza della Signoria,
 Basilica of Santa Croce
Historic horse hooks on the streets of Florence
The Palazzo Vecchio Bell Tower
View overlooking Florence
Florence Cathedral
Street view in Florence

Instead of driving, find an amazing hotel in the city and explore iconic landmarks like Ponte Vecchio bridge, the Uffizi Gallery and the Duomo cathedral on foot. When you explore Florence, you can walk in the footsteps of the masters and immerse yourself in the timeless architecture around the city. Art lovers flock here to see Michelangelo’s David and other notable works of art. Take a leisurely stroll around the city center stopping to admire some of the remnants of history that still adorn the buildings. You can still see the hooks on the facades of buildings around town. Of course you don’t want to miss the Façade of Santa Croce. It is a phenomenal example of the artistry throughout the city.

Once you’ve seen everything there is to see in Florence, go get your rental car and thoughtfully start the rest of your visit to Tuscany. Pro tip: While there are plenty of rental agencies in town, pick up your rental from one of the locations on the outskirts of town. Better yet, get the car from the airport. This will save you from the hassle of navigating around the city.

The Wine Region

Tuscany is synonymous with world-class wine. No visit to Tuscany would be complete without exploring this renowned wine region. This most certainly tops the list of best places to visit in Tuscany. Here you will find vineyards growing the Sangiovese grape and producing the regions most famous wine: Chianti Classico. Chianti is a light bodied red wine with tasting notes that include tart cherries and strawberries. Explore some of the lesser known vineyards and if you are feeling adventurous book a stay at a genuine wine estate for a few nights. There’s nothing like sleeping in a nearly 200 year old wine estate and indulging in the incredible food. One that tops the list for me is Badia a Coltibuono. It is a former monastery that today has incredibly beautiful grounds and offers cooking classes for those looking to dive deeper into Italian cuisine.

If you happen to plan your visit around the Chianti Exhibition – In Vino Veritas, you are in for a treat. Farmers come together to highlight the wines and culture of the region in the most entertaining way. Visitors descend on this area year after year for this experience. You may get the opportunity to try a pour from Italy’s oldest wine estate, Ricasoli – 900 years and counting.

Amazing Places to Visit in Tuscany

I’ve already recommended that you spend a few nights in Florence but you should definitely get out and see more of this amazing region. You will fall in love with the rolling hills adorned with vineyards everywhere. Additionally, there are some seaside villages that are truly worth visiting. I’ve listed a few of my favorites here.

Siena is a UNESCO World Heritage Site renowned for its well-preserved medieval architecture. This is what you envision when you think of charming Italian villages. Visit the Piazza del Campo which is considered the heart of the city. Pop into some of the local shops and stop for a gelato before you leave. Don’t miss the majestic Siena Cathedral with its intricate façade and stunning interior frescoes. If you are still in search of wine, make a visit to Castello di Ama. It’s one of the most impressive estates in the area.

Siena, Italy
Entry to San Gimignano

San Gimignano. I visited for the rustic charm but I’ve seen it referred to as the “Manhattan of the Middle Ages”. Legend has it the skyline was dotted with medieval towers built by wealthy families to showcase their prosperity. Today, only a few of those towers remain. Nonetheless, the city is very charming and they have a local wine called Vernaccia that you will want to sample during your stay.

Lucca is known for its Romanesque churches, elegant palaces, and charming piazzas. Take a peek through the surrounding walls to learn more about the history of this small town. Be sure to climb the Guinigi Tower for stunning views and visit the beautiful botanical gardens.

Plan your visit around the Summer Music Festival for a special treat. International artist from all genres perform during this highly anticipated event.

Inside a restaurant in Lucca
terrazza mascagni checkered terrace in livorno

Livorno is an important port city in Florence. If you are cruising the west coast of the country and the itinerary indicates a stop in Florence, you are likely stopping in Livorno. It’s actually a pretty interesting city. Walk across canals in the Quartiere Venezia (New Venice District) or simply explore the fortress at the edge of the Medici port.

Pisa, well renowned for its leaning tower, but has its own special charm. The city straddles the Arno River and is home to some twenty historic churches such as Santo Stefano dei Cavalieri.

The university Normale di Pisa is the focal point of the town. Expect to see college students and events catered to them all around town.

Leaning Tower Pisa Italy

My Perspective

I could go on and on about all of the amazing places I saw in Tuscany but the true adventure lies in the discovery of new places, food and culture. There is so much to explore, it’s hard to narrow down the best places to visit in Tuscany. While art and wine might be what brings you to the region, the landscape, architecture and food are certain to keep you coming back again and again.


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