4 days, 3 nights · Best for First-time Chianti travelers seeking wine, hill towns and quiet luxury
The Chianti Experience package with Private Driver
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 Wine Region
Hill towns, estate cellars and afternoon sun
Your hotel sits among the vineyards between Florence and Siena, where stone farmhouses give way to ordered rows of Sangiovese. The property offers pool, garden and a welcome dinner of pici pasta, wild boar and estate Chianti delivered by candlelight. You have a private driver each touring day, freeing you to photograph the cypresses, taste at the butcher counter in Greve and walk the ramparts of Monteriggioni without watching the clock.
San Gimignano's fourteen towers rise above the Val d'Elsa, visible for miles. Inside the walls you find frescoes by Gozzoli in Sant'Agostino Church and the Town Gallery's Sienese altarpieces. Montefioralle, a fortified hamlet above Greve, remains a circuit of stone houses and one chapel. At a family winery you tour barrel rooms carved into the hillside and taste Chianti Classico, Riserva and Vin Santo with cantucci. A hands-on cooking class turns local eggs, flour and greens into lunch.
Arranged for you: Private transfers from Florence, three nights countryside accommodation, welcome dinner with wine pairings, full-day private driver for San Gimignano and Monteriggioni, full-day private driver for Greve and winery visit with tasting, Tuscan cooking class, and private return transfer to Florence.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Chianti Wine Region
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Private truffle hunt with trained dog and tasting lunch Day Trips · Half day
Join a local hunter and his Lagotto in the woods, then sit down to a three-course truffle menu at a countryside trattoria.
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E-bike tour through Chianti vineyards with picnic Day Trips · Full day
Pedal assisted routes from Panzano to Volpaia, stopping at viewpoints and a family cantina for tastings.
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Private visit to a Florentine noble family's Chianti estate Day Trips · Half day
Tour the historic cellars, meet the winemaker and taste reserve bottlings not sold commercially, followed by lunch in the villa.
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Siena walking tour with Palio contrada visit Day Trips · Half day
Explore the Campo, Duomo and backstreets with a local guide, then step into a neighborhood contrada museum to learn about the horse race.
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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 Wine Region
In the afternoon, enjoy a private transfer from Florence to your charming hotel nestled in the heart of the Chianti region. Upon arrival, take the opportunity to unwind, whether by lounging beside the pool, strolling through serene gardens, or simply soaking in the peaceful Tuscan landscape. As evening falls, delight in a welcome dinner featuring local specialties and expertly paired Chianti wines, your first taste of the region’s culinary excellence. Settle in for a restful night surrounded by the rolling hills of Tuscany.
Begin your day with a classic Italian breakfast, then set off with your private driver to explore the jewels of the Tuscan countryside. Your first destination is San Gimignano, a medieval town renowned for its iconic towers and rich artistic heritage. Wander its cobbled streets, visit the Sant’Agostino Church adorned with Renaissance masterpieces, and admire the Town Gallery’s collection. Continue to Monteriggioni, a perfectly preserved medieval village with a storied past, learn about its strategic role in regional power struggles and the dramatic “great betrayal” that transferred its control to Florence. Enjoy lunch (optional) inside the village’s formidable walls. In the afternoon, arrive in Siena and immerse yourself in its medieval splendor. Marvel at the black-and-white marble Cathedral, gaze at frescoes by Ghirlandaio, and stand in the legendary Piazza del Campo, home of the Palio horse race. Later, return to your Chianti hotel for a relaxing evening and dinner at your leisure.
After a hearty farmhouse breakfast, embark on a scenic drive through the rolling vineyards of Chianti with your private driver. Your first stop is Montefioralle, a picturesque fortified village that feels frozen in time. Continue to Greve in Chianti, the vibrant heart of the region, explore its charming market square, perhaps visit the Franciscan Monastery, and sample local delicacies at a renowned butcher shop. Next, tour a celebrated local winery, delving into the art of winemaking and savoring a tasting of their best vintages. After lunch (at your leisure), return to your countryside retreat for a hands-on Tuscan cooking class. Under expert guidance, craft your own authentic Tuscan dinner, paired perfectly with local wines. Relish the fruits of your labor and enjoy another peaceful night in Chianti.
Day 4
Tavernelle Val di Pesa, Florence
Enjoy a final breakfast amidst the Chianti hills before checking out of your hotel. A private car and driver will return you to Florence, where your Tuscan countryside adventure comes to a close, leaving you with unforgettable memories of medieval towns, rolling vineyards, and the flavors of Tuscany.
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.
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Questions travelers ask
Which places are included in this vacation package?
Over 4 days this journey brings you to Chianti Wine Region, Florence, Monteriggioni, San Gimignano, Siena, and Tavernelle Val di Pesa. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
Is transportation arranged for us?
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 is this trip designed for?
It suits travelers who want Italy arranged by experts, with guided experiences balanced by free time to explore on your own.
Can the itinerary or hotels be adjusted?
Yes. Nothing here is fixed. Your travel consultant can add nights, change hotel categories, or swap experiences so the trip matches your wishes and your budget of time. A minimum of 2 travelers applies.
What time of year should we plan this vacation?
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.