Discover Tuscany at its most delicious, San Gimignano’s medieval skyline, then Chianti’s wineries and farms for wine, salami, and cheese tastings.
Private Tour Excursion to San Gimignano & Chianti Tuscany
Tour in a Day
Starting from
$
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
SAN GIMIGNANO, CHIANTI
Medieval Towns and Tuscan Tastings
- Embark on a private full-day tour through the heart of Tuscany, where medieval history and renowned cuisine come together in one unforgettable day.
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
SAN GIMIGNANO, CHIANTI
Medieval Towns and Tuscan Tastings
Begin in San Gimignano, the enchanting UNESCO World Heritage hill town celebrated for its soaring ancient towers and majestic palaces. With your expert guide, uncover the stories that shaped this iconic medieval skyline as you explore its charming streets. Then continue through the rolling landscapes of Chianti, stopping at local wineries and traditional farms to savor tastings of the region’s finest wines, artisanal salamis, and rich Tuscan cheeses. Blending cultural discovery with culinary delight, this exclusive driving tour is a perfect way to experience Tuscany’s timeless beauty and authentic flavors.
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Frequently Asked Questions
What destinations does this package visit?
This journey brings you to Chianti Wine Region, and San Gimignano. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How is transportation handled on this trip?
Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
Who will enjoy this itinerary most?
It suits travelers who want Italy arranged by experts, with guided experiences balanced by free time to explore on your own.
Can we tailor this trip to our wishes?
Yes. This sample itinerary is a starting point, and every Trips 2 Italy package is fully customizable. Your travel consultant will adjust the destinations, hotel category, pace, and experiences to fit your plans. A minimum of 2 travelers applies.
When is the best time to take this trip?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.