Tuscany, Italy Tour

The Tuscany Tour was the most awaited part of our stay in Pisa. If you’re looking for the vineyards, the view of the countryside, the old hilltop towns, and the best Tuscan sunset, then this post is for you!


Unless you are renting a car to go around, joining a tour is a good idea! We joined the Siena, San Gimignano and Chianti Wine Tour from Pisa organized by Bella Italia Tour. Note that there are no direct public transportation connecting the three areas.

For 98 EUR, the tour includes:

  • Free pick up from your hotel in Pisa city
  • Group of 8 people max
  • Travel by Minivan with AC
  • Tour Guide (English)
  • Tour Siena, San Gimignano
  • Chianti wine tasting in a local cellar with lunch
  • Duration of the trip: 9 hours (estimated)

We were picked up near the Tower of Pisa at 7:30am. Don’t be late because they are strict with the time. Don’t forget to pee as well before the tour because they don’t do stop-overs. We were dropped in Florence to ride a bus with other tourists.

This tour is also memorable because I had to pee in a small Lays chips plastic container inside the bus while the tour guide was talking. I was trying to wait till we get to San Gimignano but more than an hour of holding it in was just too challenging. I had to go! (Too much information but it was really funny and a bit embarrassing!) So people, pee before the tour!

First Stop: San Gimignano

Historic Center of San Gimignano (UNESCO WORLD HERITAGE SITE)
Walking around the city
Shops in San Gimignano
Wine Tasting
Old Alleys


City Center
View while looking for the 13 towers
We cannot stop taking photos of these old alleys!
Gelato everywhere!

San Gimignano is an old medieval hill town showcasing Romanesque and Gothic architecture and famous for its 13 towers, located in the province of Siena. It is also known as the Town of Fine Towers. The Historic Center of San Gimignano is a UNESCO World Heritage Site. You can go inside the shops and taste some local delicacies and wine!

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The famous Gelateria Dondoli!
Lining up!
What flavor to choose?
Find your flavor!
Who’s excited for ice cream?

Don’t forget to also taste the famous gelato- Gelato Dondori! It is located in the center of Piazza della Cisterna in San Gimignano. Try the famous Crema di Santa Fina (cream with saffron and pine nuts), one of the best sellers! The ice cream is known for its highly selected quality ingredients mostly from the region. This is visited by famous celebrities and both local and international media publications!

Second Stop: Chianti Hills – Casa Frassi

The view driving around Chianti
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Casa Frassi
Casa Frassi Wine and Lunch place
OOTD Walls

Casa Frassi is both a hotel and winery situated in one of the hilltops of Chianti. We stayed there for the local wine tasting and lunch. The wine was great and they even explained the different types of red and white wine. The food, don’t expect much. The view of vineyards going there was also a site to see!

Best part of lunch – Aperitivo
Chianti Red Wine
Yes the wine was good!

Third Stop: Siena

Siena is one of the cities in Tuscany known for its historic center declared as a UNESCO Heritage Site. Almost the whole of Tuscany is a Heritage site!

Piazza del Campo – City Center
We took a break and had coffee in one of the cafes in Siena

Visit the Siena Cathedral, a medieval church now dedicated to Mama Mary.

Siena Cathedral
Siena Cathedral

Palazzo Salimbeni houses Banca Monte dei Paschi di Siena, one of the oldest banks in the world. Its façade is also famous for its Gothic style .

Palazzo Salimbeni
Palazzo Salimbeni

Palazzo Pubblicco is a palace located in the center of Siena. Like the other structures, it was also influenced by the Gothic architecture. The bell tower is called the Torre del Mangia designed to be one of the tallest structure in Italy. The design was applied to other towers in England.

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Piazza Del Campo is the heart of the medieval city where the three main roads lead to.  It is surrounded by cafes and restaurants and tourists flock at the center where they sit and hang-out. The piazza also hosts major events like the Palio, famous horserace event in Italy.


Bonus stop: Monteriggioni

We spent the rest of the afternoon till sunset in Monteriggioni, a municipality in Siena situated at the border of Florence and Siena. It is a great place for honeymoon or if you just want to spend a quiet time overlooking the vineyard together with at least 40 residents of the area. They have a few hotels, shops and restaurants to keep you entertained. It is also popular for being used by Dante Alighieri in his work, Divine Comedy.

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Small shops in Monteriggioni
Restaurant in Monteriggioni
House in Monteriggioni
Photo worthy walls all around!
Restaurant at the center
Hand crafted jewellery shop
Small church at the center

That ends our tour! The whole day felt like we were time-warped to the medieval ages! We were dropped off by the bus in Florence and met our minivan driver to take us back to Pisa.

I’d definitely want to see these areas again!

Second to the last stop: The City of Love, Venice!

Follow me IG: @lencaccam for random trips and daily musings!

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