Siena Duomo and old town skyline

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


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

Overall Rating (2 reviews)
5.0 out of 5
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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

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

Highlights of Rome and 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

Explore the birthplace of the Renaissance in all its splendor. Discover Rennaissance art in Florence, browse bustling markets for fresh produce and cured meats and stroll through narrow medieval streets to see the 1,000-year-old Ponte Vecchio bridge. Head to the Tuscan countryside to visit Siena and see the medieval Monteriggioni fortress and learn the secrets behind a homemade Italian meal.

Rome, Orvieto, & Florence - 9 Days

This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint.