2 days, 1 nights · Best for Wine lovers seeking Tuscan countryside immersion
The Chianti Experience package with Private Driver
Nights Accommodation in a characteristic Countryside Hotel in the Chianti Region; Visit Siena, San Gimignano, Monteriggioni and much more!
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Chianti Wine Region, Tuscany
Chianti
Vineyards, cellars and medieval towns with private driver
We base you in the Chianti hills among vineyards that have made Sangiovese famous since the thirteenth century. Your private driver collects you each morning for tastings at estates where winemakers pour Chianti Classico, Riserva and super-Tuscans in barrel rooms and Renaissance cellars. Between vineyards we trace the stone towers of San Gimignano and the Campo in Siena, where the Palio runs every July and August.
A cooking class in a farmhouse kitchen teaches you pici, ribollita or pappa al pomodoro under the direction of a Tuscan cook. You sit down to the dishes you have made with a glass of the region's namesake red, olive oil from the grove outside and bread still warm from the oven.
Arranged for you: We arrange a private driver, winery visits with tastings, access to San Gimignano and Siena, and a hands-on Tuscan cooking class with wine pairing.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Chianti
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Private truffle hunt and tasting lunch Day Trips · Half day
A hunter and his dog lead you through oak woods in search of white or black truffles, followed by a multi-course lunch featuring your finds.
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Guided walk through a Chianti vineyard Day Trips · Half day
An estate viticulturist explains pruning, harvest timing and Sangiovese clones as you walk the rows, ending with a vertical tasting of single-vineyard bottlings.
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Artisan ceramic studio visit in Montelupo Day Trips · Half day
A fourth-generation ceramicist demonstrates traditional maiolica techniques in a workshop that has supplied Tuscan tables since the Renaissance.
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Private sunset aperitivo at a castle estate Day Trips · Half day
Prosecco and Tuscan appetizers served on a castle terrace as the sun sets over vineyards that once provisioned Medici Florence.
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A Day Tour in Tuscany By Bike Guided Tours and Sightseeing · Tour in a DayBreathe in the fresh air and feel the Tuscan sun on your face, while touring the Chianti region on bike!
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Private Tour Excursion to Chianti Tuscany Guided Tours and Sightseeing · Tour in a Day
Medieval history and Tuscan cuisine combine on this full day driving tour.
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Private Tour Excursion to San Gimignano & Chianti Tuscany Guided Tours and Sightseeing · Tour in a Day
Discover Tuscany at its most delicious, San Gimignano’s medieval skyline, then Chianti’s wineries and farms for wine, salami, and cheese tastings.
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The Chianti Wine Tasting Small Group Tour from S.Gimignano Food and Wine · Tour in a DaySip and savor your way through Chianti. Vineyard views, winery tastings, and Tuscan bites of cheeses, cold cuts, and classic cuisine.
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The Chianti Wine Tasting Small Group Tour from Siena Food and Wine · Tour in a DayImmerse yourself in the picturesque beauty of the Chianti countryside on this half-day tour, where rolling hills and lush vineyards set the scene for an unforgettable Tuscan adventure.
Day by day in Chianti
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.
Day 2
Departure
A private transfer to the airport. We stay on the line until you are home.
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
Hear from travelers who have planned Italy with us
They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
Ready to make it yours?
Send us this adventure with your changes. An Italian-born planner builds the first full draft and calls you to walk through it.
Or call 1-866-464-8259
Questions travelers ask
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.