Tuscany Day Trip from Florence: Chianti, Siena & San Gimignano, Florence

5.0 (9 reviews)

Overview

Discover the picturesque region of Tuscany, known for its historic hilltop towns, rolling hills scenery, delicious cuisine, and world-famous wines. This guided tour will help you experience all that Tuscany offers in an authentic, relaxed way. You’ll visit the beautiful medieval towns of Siena and San Gimignano, savor a traditional lunch, join a wine-tasting, and watch an authentic Italian pasta-making demonstration at a Chianti farmhouse and vineyard. Your friendly, English-speaking guide will teach you about the sites you pass, the towns you visit, and the food and wine you consume. 

You’ll meet your guide in central Florence and learn a bit about the itinerary. From start to finish, the emphasis of your day is indulgence! Indulge in stunning scenery, delicious wines, and lazy strolls on an all-inclusive Tuscan adventure. Start with a scenic transfer into the beautiful hills of Tuscany, stopping first in Siena. Miraculously spared during the bombings of WWII, this hilltop village is an incredible example of medieval town planning and architecture.

Famous for its wine of the same name, Chianti is a beautiful area full of rolling hills and picture-perfect farmhouses. Enjoy lunch and a wine tasting at one of these authentic Chianti farms, starting first with a property tour of its vineyards and wine cellars. Pair your lunch with a guided wine tasting and learn a few cooking tips as you watch an Italian pasta-making demonstration. What you eat will depend on the season, as Tuscan cuisine is famous for its seasonal produce. Traditional dishes use only the best and freshest ingredients.

Next, explore the historic Tuscan town of San Gimignano, an architecturally significant UNESCO World Heritage Site. You'll enjoy a full tour of the city, then have free time to shop for souvenirs or climb the city’s campanile for some of the best views in Tuscany. You’ll then return to Florence.

Read more about unique and interesting experiences in and around Florence.

Like what you see?

Chat with our local specialists and let us help you customize your trip with experiences like this.

Get started

Traveler reviews

9 total ratings, 7 with reviews
5.0
Feature ratings
Quality of Experience
5.0
Food
5.0
Guides, Drivers and Staff
5.0
Transport
4.9
Sam
Sam H.
Richmond, VA | Reviewed on Sep 22, 2024
Our group of 8 enjoyed a wonderful day of food, wine and new friends! Highly recommend this tour. We were able to enjoy a full day in Tuscany with a small group. Our guide was very knowledgeable and friendly. Read more

Our group of 8 enjoyed a wonderful day of food, wine and new friends! Highly recommend this tour. We were able to enjoy a full day in Tuscany with a small group. Our guide was very knowledgeable and friendly.

Quality of Experience
Food
A wonderful lunch was served with more amazing wine!
Guides, Drivers and Staff
Transport
Karisa
Karisa W.
Seattle, WA | Reviewed on Jul 11, 2024
Loved our tour guide and the wineries were great! Read more

Loved our tour guide and the wineries were great!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
D
Diane S.
Chicago, IL | Reviewed on Jun 21, 2024
Guide was fantastic. The rather intimate small group we had made it more fun Read more

Guide was fantastic. The rather intimate small group we had made it more fun

Quality of Experience
Food
Lunch at the tuscany villa was awesome
Guides, Drivers and Staff
Very punctual
Transport
A
Ashley S.
Chandler, AZ | Reviewed on May 18, 2024
We lucked out with having no one else registered for our tour at the same time so we had our guide and the tours all to ourselves...and it was fabulous! Our driver was wonderful and we had a great time sharing stories and learning about the region. Would highly recommend! Read more

We lucked out with having no one else registered for our tour at the same time so we had our guide and the tours all to ourselves...and it was fabulous! Our driver was wonderful and we had a great time sharing stories and learning about the region. Would highly recommend!

Quality of Experience
Food
Guides, Drivers and Staff
Transport
M
Mary SUe J.
New Castle, PA | Reviewed on Sep 18, 2023
wonderful experience. Read more

wonderful experience.

Tips for future travelers

not at the present time

Quality of Experience
Food
Guides, Drivers and Staff
Transport
Allison
Allison H.
Richmond, VA | Reviewed on Apr 25, 2023
This small group tour took us through the Tuscan countryside, where we tasted wine and olive oil at various locations. It was a delightful experience. We even got to bring home some wine and olive oil. Read more

This small group tour took us through the Tuscan countryside, where we tasted wine and olive oil at various locations. It was a delightful experience. We even got to bring home some wine and olive oil.

Quality of Experience
Food
Guides, Drivers and Staff
Transport
L
Lauri F.
Pittsburgh, PA | Reviewed on Oct 04, 2022
Our guide for this was so personable and the small group was easy to get to know. Loved seeing and learning about all the places we went. Read more

Our guide for this was so personable and the small group was easy to get to know. Loved seeing and learning about all the places we went.

Tips for future travelers

The free time isn’t long in either Sienna or San Gimignano so think ahead of time about how you want to spend it.

Quality of Experience
Guides, Drivers and Staff
Transport

Like what you see?

Chat with our local specialists and let us help you customize your trip with experiences like this.

Get started

Itineraries with Tuscany Day Trip from Florence: Chianti, Siena & San Gimignano