2 days, 1 nights · Best for wine lovers seeking Tuscany's finest Brunello
The Brunello Wine & Montalcino Small Group Tour from S.Gimignano
Savor the world-class Brunello wines as you visit renowned wineries in Montalcino, enjoying exclusive tastings and learning about the region’s rich winemaking traditions.
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 1San Gimignano, Tuscany
San Gimignano
medieval towers and Montalcino's finest Brunello
We collect you in San Gimignano for a full-day exploration of Montalcino, the small hill town whose Sangiovese Grosso vineyards produce Brunello, one of Italy's most prized wines. Your English-speaking guide leads you through family estates where oak barrels line cool cellars and five-year aging is the rule, not the exception. Between tastings you move through the Val d'Orcia, a UNESCO landscape of cypress-lined roads and fortified farmhouses.
The day returns you to San Gimignano by evening. We arrange the vehicle, the guide and winery access, leaving you free to compare vintages and learn why Brunello commands the prices it does.
Arranged for you: Private vehicle with English-speaking driver, local expert guide, winery visits with tastings in Montalcino
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in San Gimignano
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Private cooking class in a Tuscan farmhouse Day Trips · Half day
Learn handmade pici and ribollita with a local cook in a working kitchen, then lunch on what you prepare.
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Guided walk through medieval San Gimignano Day Trips · Half day
Explore the tower houses, Romanesque Collegiata and frescoed chambers with an art historian.
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Vernaccia wine tasting at a San Gimignano estate Day Trips · Half day
Sample the town's indigenous white grape at a hillside cantina with the winemaker.
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Truffle hunting in the Tuscan woods Day Trips · Half day
Follow a trained dog and its handler through oak forests, then taste your finds over lunch.
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Escorted sightseeing tour of Montepulciano & Pienza departing from S.Gimignano Guided Tours and Sightseeing · Tour in a DayDiscover the artistic and scenic treasures of Val d’Orcia with a guided tour of Pienza and Montepulciano, two jewels of Tuscany.
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Private Tour Excursion to San Gimignano & Chianti Tuscany Guided Tours and Sightseeing · Tour in a DayDiscover 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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Private Tour Excursion to Siena & San Gimignano Guided Tours and Sightseeing · Tour in a DayDiscover Tuscany’s legendary charm in style, explore Siena and San Gimignano with the luxury of your own private driver.
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The Brunello Wine & Montalcino Small Group Tour from S.Gimignano Food and Wine · Tour in a DaySavor the world-class Brunello wines as you visit renowned wineries in Montalcino, enjoying exclusive tastings and learning about the region’s rich winemaking traditions.
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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.
Day by day in San Gimignano
Travel in comfort through the scenic Tuscan countryside in a private vehicle, accompanied by an English-speaking driver and a local expert guide from San Gimignano. Savor the world-class Brunello wines as you visit renowned wineries in Montalcino, enjoying exclusive tastings and learning about the region’s rich winemaking traditions, all while taking in the breathtaking landscapes that make Tuscany unforgettable.
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?
This journey brings you to Montalcino, 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 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.