Tour of Tuscany: Blue Skies, Vineyards, and Horses

Tour of Tuscany

What is the best way to explore and see most of Tuscany when you are 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
This post may contain affiliate links. I may receive commissions for purchases made through links in this post that fund my travels at no extra cost to you. Please read my disclosure for more info.

Tour of Tuscany

SienaSienna skyline

The first stop on the Tuscany tour is to 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 that holds the infamous Palio medieval horse race twice a year. 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! Crowds watching the Palio Horse Race in SienaJockeys and Horses in the PalioPalio Race course in Piazza del Campo

I wasn’t able to 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. There were people wearing their colors for their neighborhood out of the ten that are represented in the race. The town has flags flying on every building and the streets are so alive with revelers after the race. I even saw the end of a parade with flag twirlers just like in the movie, Under the Tuscan Sun. The town has so many sights for you to explore like the Siena Cathedral, 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.Piazza del Campo

ChiantiMazzarrini Vineyard

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 it was approved by the government 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), which happens to be my favorite out of the ones I tasted. I also tried their Balsamic Vinegar that was added on cheese and Truffle Oil on bread. All in all, Poggio Ai Laghi is an amazing venue for lunch and the wine is superb.Poggio Ai Laghi

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 up 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 through the many shops or stop into 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.

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€ and are 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.Piazza della Cisterna

View from Torre Grossa

PisaHeather 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 amount of time of our visit, I wasn’t able to to 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 do want to climb up the Leaning Tower of Pisa, you will need to buy a timed ticket. These tickets go fast. There is only a limited quantity, so you need to purchase your ticket early or you will have to wait for 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 that I chose for this tour of Tuscany is Get Your Guide. I was not sponsored for this tour. Most of the time I enjoy exploring new places on my own, but sometimes I like to take group tours. This is a great way to see a large swath of an area and to 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 do help me out so I can continue sharing my travel stories with you.


Taking a Tour of Tuscany is a wonderful way to see the highlights of the region. As I was staying in Florence for a week, this was one of my best ideas I had 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 need to plan for on my next trip to the area. Especially I want to try more wine tastings in Tuscany. Exploring a day in Tuscany was an amazing experience for me and I’m sure will be for you as well.

If You Enjoyed This Tour of Tuscany Post, Sign Up To Receive Posts By Email or…

Join us on Facebook for regular updates and related articles
Check us out on Instagram to see what we are up to in photos
Follow us on Twitter for links to great travel articles curated just for you
View and purchase your favorite of my travel photos on SmugMug. And if you don’t see the one you want on the site, send me a comment below, and I’ll add it.
Or share this “Tour of Tuscany: Blue Skies, Vineyards, and Horses” with others by pinning on Pinterest!

Tour of Tuscany Pinterest Pin

Further Reading

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

1 Comment

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.