Cycle the rolling heart of Tuscany from a San Gimignano, seeing vineyard roads, Vernaccia and Chianti tastings, medieval hill towns, and perfectly paced rides with expert support.
Explore Tuscany countryside by bike tour
4 Days/3 Nights
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
Bike Fitting and Settling in
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Arrive in San Gimignano and check in to your hotel
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Afternoon bike fitting and assistance to select the perfect bicycle
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Free evening for personal exploration and dinner
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Overnight stay in San Gimignano
Day 2
SAN GIMIGNANO AND SURROUNDING TOWNS
Countryside Riding
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Breakfast at your hotel
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Guided bike excursion through the scenic San Gimignano countryside
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Visit a local wine estate for Vernaccia di San Gimignano wine tasting and light lunch
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Return to hotel in the afternoon
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Overnight stay in San Gimignano
Day 3
CHIANTI AND SURROUNDING TOWNS
Broli, Gaiole and a Picnic Lunch
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Breakfast at your hotel
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Private minibus transfer to the Chianti region
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Bike tour featuring Brolio Castle, Gaiole in Chianti, and Radda in Chianti
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Picnic lunch en route
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Visit a local wine cellar for Chianti wine tasting
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Return to hotel in the late afternoon
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Overnight stay in San Gimignano
Day 4
SAN GIMIGNANO
Arrivederci, Tuscany!
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Breakfast at your hotel
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Check out and end of services
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
SAN GIMIGNANO
Bike Fitting and Settling in
Arrive in the picturesque medieval town of San Gimignano and settle into your comfortable hotel. In the afternoon, meet with our experienced staff for a personalized bike fitting, ensuring you have the ideal bicycle for your upcoming adventures. The rest of the evening is yours to explore San Gimignano’s charming streets and enjoy dinner at your leisure. Overnight at your hotel accommodation.
Day 2
SAN GIMIGNANO AND SURROUNDING TOWNS
Countryside Riding
After a hearty breakfast, meet your guide and set off on a scenic bike ride through the rolling hills and vineyards surrounding San Gimignano. Along the route, stop at a renowned wine estate to sample the celebrated Vernaccia di San Gimignano and enjoy a light Tuscan lunch. Cycle back to your hotel in the afternoon, with the evening free for relaxation or further exploration. Dinner is on your own, followed by another restful overnight stay.
Day 3
CHIANTI AND SURROUNDING TOWNS
Broli, Gaiole and a Picnic Lunch
Begin your day with breakfast before transferring by private minibus to the heart of the Chianti region. Embark on a memorable bike tour, taking in the breathtaking scenery of Brolio Castle, Gaiole in Chianti, and Radda in Chianti. Pause for a delightful picnic lunch and enjoy a guided visit with wine tasting at a local Chianti cellar. Return to your hotel in San Gimignano by late afternoon. The evening is free for dinner and relaxation. Overnight stay at your hotel.
Day 4
SAN GIMIGNANO
Arrivederci, Tuscany!
After breakfast, check out from your hotel. Depart San Gimignano making the end of our services.
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Frequently Asked Questions
What destinations does this package visit?
Over 4 days 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 independent travelers who love the freedom of the open road with the security of arranged hotels and routing.
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.