Remember the movie Under the Tuscan Sun? Remember the Tuscan village full of charm and romance? The movie perfectly portrays the heart of the region – Tuscan countryside. This is where you will find gently rolling hills, beautiful meadows, dreamy inns, and inviting vineyards of Chianti. But it is not all that the region has to offer. Let’s discover Florence overflowing with art and culture, Pisa with its leaning tower, and UNESCO World Heritage Site – San Gimignano. In this post, I will navigate you through this fascinating part of Italy. We will take a look at highlights of Tuscany and learn what to do there, other than just take in the views. I guarantee that in the end, you will ask yourself: wouldn’t it be nice to vacation there?  

Countryside of Tuscany. Vineyards.Getting lost in the countryside is a top thing to do in Tuscany.


Discover Tuscany countryside
Visit a winery
Take a day trip to San Gimignano
Spend at least two days in Florence
Take a day trip to Pisa
Visit Siena
Enjoy the food of Tuscany

My visit to Tuscany was a part of the month-long European road trip with my sister. Our itinerary was rather intense so after visiting Amsterdam, Zermatt in Switzerland, and stunning Cinque Terre in Italy, we planned to spend a more relaxing time in this part of Italy, concentrating on the Tuscany countryside.

I picked our hotel in the middle of the region, not too close to major attractions to avoid crowds. If you are looking for charm and relaxation, Podere Benintendi delivers just that. Our room was simple and well priced but had everything we needed.

The beauty of the hotel was its location and grounds, they spelled: TUSCANY! Just picture perfect.

Podere Benintendi hotel's ground located in the heart of Tuscany.
Charming Podere Benintendi hotel in the heart of Tuscany.

Discover Tuscany countryside

I recommend exploring the Tuscany countryside as the top thing to do in the region. Do not worry if you get lost, just enjoy the beauty around you, where all the elements fall together into one idyllic experience.

Think gently rolling hillsides, rows of green cypress trees, sandy roads leading to rust-colored farmhouses, castles, vineyards, and flowers. You will only have one thought: this scenery is heavenly! Here are some of the most beautiful scenic drives in Tuscany. 

Looking into what do in Tuscany? Learn about highlights of Tuscany : Florence, Pisa, San Gimignano, and dreamy countryside with inviting wineries, #highlightsoftuscany #whattodointuscany

Visit a winery

For wine lovers, highlights of Tuscany definitely should include the Chianti region. There are plenty of wineries to choose from so you can spend a whole day tasting.  On limited time, pick just one or two and have a long and relaxing visit.

We passed quite a few wineries on the Chianti route, but did not stop until we came across Castello Gabbiano – a charming castle, quintessential Tuscan scenery, complemented by great wine! We could not ask for anything more.

Castello Gabbiano winery in Chianti Tuscany.
Castello Gabbiano winery in Chianti Tuscany.

The Castle dates back to 1124 and has been used through the centuries as a private residence. In the year 2004, it was renovated and changed into a hotel facility. It offers apartments to rent, a gourmet restaurant, and a wine store with tasting.

Castello Gabbiano restaurant in Chianti Tuscany.
Castello Gabbiano restaurant in Chianti Tuscany.

Take a day trip to San Gimignano

For many visitors, charming villages are the highlights of Tuscany, but you do not have to see them all. Just like with wineries, you can pick one that speaks to you, and spend a day there. Our choice was San Gimignano in the Chianti region, famous for its medieval architecture characterized by tower houses.

San Gimignano in the Chianti region of Tuscany.
San Gimignano in the Chianti region of Tuscany.

UNESCO World Heritage Site since 1990, the village is one of the most iconic destinations in Tuscany and therefore experiences a high number of visitors. I suggest visiting in the morning or in the evening when day trip buses are not there.

If you like to shop, San Gimignano will satisfy your appetite with amazing art stores, leather goods, and pottery.

Pottery shop in San Gimignano Tuscany.
You will find beautiful Italian pottery in San Gimignano Tuscany.

Spend at least two days in Florence

My visit to Florence was not a part of the European trip with my sister. I visited it solo and sick with a really bad cold, which took out one of three days from my itinerary. Also, it was August, which means heat and crowds. Somehow, I still managed to fall in love with the city.

During the day, I found the rescue from the heat in museums and beautiful city parks. I stayed in Hotel Lorena, a good option for budget travelers looking for simple accommodation in the heart of the city within a walking distance to all major attractions.

View of beautiful Florence Italy.
Just another view of beautiful Florence.

Florence is a very stimulating city, famous for art and architecture, but what comes with it is crowds. You need to plan your visit strategically, practically hour by hour. Make sure to purchase priority passes with a designated entry time to famous attractions or you spend hours waiting to get in.

The best and cheapest way to obtain priority passes is online.

A walk along the river in Florence.
What to do in Florence? One of the highlights is just walking its streets.

My personal favorite was The Uffizi Gallery, one of the world’s top art museums with some of the most important works of the Renaissance, including works by Leonardo da Vinci. Here you can find the best thing to do in Florence.

Piazza Signoria in Florence Tuscany.
One of the most popular sites in Florence, Piazza Signoria.

If you are interested in off the beaten path attractions of Florence, check out practically unknown park Giardino Delle Rose (The Rose Garden) which is free of charge, intimate, and one of a kind.  You will find there a series of bronze sculptures among the beautiful rose alleys. This hilly park will award you with one of the best views of Florence.

View of Florence Tuscany from Giardino Delle Rosse.
View of Florence Tuscany from Giardino Delle Rose.

Take a day trip to Pisa

The Leaning Tower has made Pisa famous all over the world. Loads of tourists come and go every day, mostly to take a look and snap a photo with the tower. It could get overwhelming. I suggest coming early or later at night if you want a pleasant experience.

We gave up on even taking a decent photo and decided to get a good lunch and a drink instead. For more things to do in Pisa, check out 1 day in Pisa itinerary

Two sisters visiting in front of leaning tower of Pisa.
Sisters on the go in Pisa Tuscany.

Visit Siena

We did not have enough time to visit Siena, but it should be on your Tuscany itinerary. I need to return to Italy for that but until then, learn here about Visiting Siena in One Day.

Enjoy the food of Tuscany

For food lovers, tasting local specialties tops highlights of Tuscany. When traveling to the region, you should definitely budget for eating out. For the best experience, follow one rule, stay away from touristy places. The farther away you go, the better the food you will get. Learn more about traditional Tuscan food.

Tuscan food in an outdoor restaurant.
Step away from touristy places to enjoy a local flavor of Tuscany.

Best time to visit Tuscany

I am sure Tuscany is beautiful at any time of year, but spring must the best time to visit, preferably May. This is when everything is blooming, temperatures are already pleasant and crowds did not arrive yet.

Red poppies along the countryside of Tuscany.No better time to visit Tuscany than spring.

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