Nights Accommodation in a characteristic Countryside Hotel in the Chianti Region; Visit Siena, San Gimignano, Monteriggioni and much more!
The Chianti Experience package with Private Driver
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
CHIANTI
Hilltown Towers And Wine-Poured Hours
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
CHIANTI
Hilltown Towers And Wine-Poured Hours
Experience the enchanting Chianti region and the heart of the Tuscan countryside with a stay in a cozy Bed and Breakfast surrounded by rolling vineyards and medieval villages. Enjoy the convenience of a private driver as you visit renowned Chianti wineries and explore the picturesque towns of San Gimignano and Siena. Enhance your journey with a hands-on Tuscan cooking class, where you’ll learn to prepare traditional dishes and savor your creations paired with a signature glass of Chianti red wine, creating unforgettable memories in this idyllic Italian setting.
This Package Includes:
This Package Does Not Include:
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Frequently Asked Questions
Where will we travel on this itinerary?
Over 4 days this journey brings you to Chianti Wine Region. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How will we get around during the vacation?
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.
What kind of traveler is this package for?
It is made for food and wine lovers who want to taste their way through Italy with tastings, local dishes, and the stories behind them.
Can we customize this itinerary?
Absolutely. Every Trips 2 Italy itinerary is designed to inspire and can be tailored end to end, from the number of nights and hotel categories to the experiences along the way. A minimum of 2 travelers applies.
What is the best season for this itinerary?
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.