Siena Duomo and old town skyline
Siena Duomo and old town skyline

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

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.

Traveler reviews

5 total ratings, 3 with reviews
5.0 out of 5
Feature ratings
Quality of Experience
5.0
Food
5.0
Guides, Drivers and Staff
5.0
Transport
4.8
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

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

Highlights of Rome & Florence - 7 Days

Your trip to Rome and Florence starts with guided tours through Rome's historical core, Vatican City, and the Roman Forum, with walks through the Colosseum and to the top of Palatine Hill. Head to Florence to experience its historic squares, cathedrals, and museums, plus an Italian cooking class to learn how to make traditional pasta and dessert. End your trip in the Tuscan countryside with visits to Siena and San Gimignano, complete with walking tours and a wine tasting.

Highlights of Florence - 6 Days

Bring your walking shoes for this itinerary, perfect for first-timers in Florence. In less than a week, you'll meander all over the city, exploring the finest art and architecture, elegant gardens, hip neighborhoods, and food markets. You'll also take two incredible day trips to Tuscany (for medieval hill towns and wineries) and the Cinque Terre (for coastal hiking trails and seafood), returning each night in time for predinner "aperitivos."

Rome, Orvieto & Florence - 9 Days

This classic nine-day trip through Italy combines two of its most cultural cities with stops in the beautiful countryside. First, land in Rome to spend quality time in the Vatican and Colosseum before taking a train to Orvieto in the Umbria region—the country's green heart. Spend a night here before you continue to Florence, the birthplace of the Renaissance, where you'll take a walking tour, learn how to make fresh pasta and drive through Tuscany to finish the adventure.