Tour of Tuscany: Blue Skies, Vineyards, and Horses

Tour of Tuscany

What is the best way to explore and see most of Tuscany in Italy? Schedule a day trip to experience the highlights that Tuscany has to offer. Whether it is the aroma of wine, green landscapes filled with olive trees and grapevines, or the narrow Italian streets that lead to large town squares, a Tour of Tuscany will provide an unforgettable experience.

Tour of Tuscany
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Tour of Tuscany

SienaSienna skyline

Crowds watching the Palio Horse Race in Siena
Jockeys and Horses in the Palio
Palio Race course in Piazza del Campo

The first stop on the Tuscany tour is the lovely town of Siena. Siena is one of the most visited cities in Tuscany, and as a medieval town filled with monuments, palaces, and cathedrals, it is no wonder. Its historic city center is a UNESCO site holding the infamous Palio medieval horse race twice yearly. I was so fortunate to schedule my Tour of Tuscany on one of the days that the Palio race is being held. What a sight to see!

Piazza del Campo

I couldn’t get close enough to be inside the Piazza del Campo during the race, but I did go in once the race was finished. The town of Siena is very festive during the Palio. People wore their colors for their neighborhood out of the ten represented in the race. The town has flags flying on every building, and the streets are alive with revelers after the race. I even saw the end of a parade with flag twirlers, like in the movie, Under the Tuscan Sun. The town has many sights to explore, like the Siena Cathedral, the Basilica of San Domenico, and the Sanctuary of Santa Caterina. Our last stop in Siena had us sampling truffles. Yum! I only had a short time in Siena, but I definitely want to go back and spend a full day exploring this cute medieval town.

ChiantiMazzarrini Vineyard

Poggio Ai Laghi

We were treated to lunch at Poggio Ai Laghi by the Mazzarrini Family in the Chianti region in the heart of Tuscany. There were wine tastings along with a delicious lunch. I tried Vermentino IGT, Morellino Di Scansano DOCG, and Chianti Classico DOCG. The DOCG means the government approved it, and the wineries chosen to make it can only produce a limited amount. Only nine wineries in Italy can make the Chianti Classico DOCG (King of Red Wine), my favorite of the ones I tasted. I also tried their Balsamic Vinegar added to cheese and Truffle Oil on bread. Overall, Poggio Ai Laghi is an amazing venue for lunch, and the wine is superb.

San GimignanoSan Gimignano - Tour of Tuscany

San Gimignano, the Town of Fine Towers, is an imposing Italian medieval town fortified by walls and perched high on a hill. In its heyday, there were 72 towers within the city; now, only 14 are preserved. When walking into this town, there are many choices in which direction you can go. There are the roads that take you along the walls that provide you with amazing views of the surrounding Tuscan landscape. Or you can walk along the main road to browse the many shops or stop at the Museum of Torture for a more exciting adventure. As you wander around the town, though, most people end up at the main square, Piazza della Cisterna.

Piazza della Cisterna

There are a couple of highlights and must-sees when visiting San Gimignano. First is to climb Torre Grossa, the highest tower in the city, where you can get astounding panoramic views of Tuscany. Plus, before you climb up the tower, you will be able to admire the 14th-century frescoes on the exterior of the building. Tickets are 9€, good for two days, and include all local museums. The second is to buy ice cream at Gelateria Dondoli in the Piazza della Cisterna, known for the best ice cream in the world. You can always find a long line of people waiting for a scoop. San Gimignano will give you great instagrammable views of the Italian countryside.

View from Torre Grossa


Heather holding up the Leaning Tower of Pisa

The last stop of our Tour of Tuscany is Pisa. Truthfully, I wasn’t very impressed with this destination. It was too crowded, and for the short time of our visit, I couldn’t do too much. I did get the obligatory photo of holding up the Leaning Tower of Pisa. There are other places to visit in the Piazza dei Miracoli, like the Cathedral and the Baptistry. If you want to climb up the Leaning Tower of Pisa, you must buy a timed ticket. These tickets go fast. There is only a limited quantity, so you must purchase your ticket early, or you will have to wait a long time before you can go up. Here are more suggestions for you of things to do in Pisa.

Get Your Guide

The group I chose for this tour of Tuscany is Get Your Guide. I was not sponsored for this tour. I enjoy exploring new places alone most of the time, but sometimes I like to take group tours. This is a great way to see a large swath of an area and meet new people, which is always nice when traveling solo. If you are interested in booking a tour with Get Your Guide, go ahead and check them out below. The link doesn’t cost you anything extra, but they help me continue sharing my travel stories.


A Tour of Tuscany is a wonderful way to see the region’s highlights. As I was staying in Florence for a week, this was one of my best ideas for day trips from Florence. I could have easily spent more than one day in Tuscany, but it gave me a nice taste of what I must plan for on my next trip there. I especially want to try more wine tastings in Tuscany. Exploring a day in Tuscany was an amazing experience for me, and I’m sure it will also be for you.

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Further Reading

If you are coming to Italy for a visit, check out these posts for further travel inspiration:

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