Skip the big commercial groups and discover Tuscan wine country the way it's meant to be explored — in a small group of no more than 8 guests. Our English-speaking guides lead you through the rolling hills of Chianti Classico, Brunello di Montalcino and Nobile di Montepulciano, stopping at handpicked, family-run wineries most visitors never find.
Each tasting is paired with genuine Tuscan cuisine, and for guests who want something extra, we also offer truffle hunting combined with a wine tasting — a rare addition to a day among the vines.
This isn't a tour picked off a shelf.
Never more than 8 guests per tour, so there's time to talk with the winemakers, linger over each glass, and explore at an unhurried pace.
We visit estates chosen for character, not convenience — tasting Chianti, Chianti Classico, Brunello di Montalcino and Super Tuscans straight from the people who make them.
Every tasting is matched with local specialties — bruschetta, artisan cheeses, house-made pasta and fine olive oil — plus a traditional Tuscan lunch at one of the wineries.
Join an expert truffle hunter and their trained dog in the forest, then sit down to a truffle-infused meal paired with fine Tuscan wines.
Seven different ways to discover the wines, food and people of Tuscany — all departing from Florence.
Small group · Full dayA half-day shared tour to two Chianti boutique wineries, tasting Chianti Classico, Riserva, and Super Tuscan wines.
DailyDeparts 9:30 AM
Small group · Full dayA shared full day (max 8 guests) tasting Vernaccia di San Gimignano at two boutique wineries in the medieval town.
Mon–SatDeparts 9:30 AM
Small group · Full dayA small-group day across three Chianti Classico wineries, tasting Chianti and Super Tuscan wines with a family-style lunch.
Mon–FriDeparts 9:30 AM
Small group · Full dayA 7-hour shared tour through Chianti Rufina's medieval castles and villas, with a sommelier-guided tasting and lunch.
Tue, Thu, SatDeparts 9:30 AM
Small group · Full dayA shared full-day trip from Florence to Montalcino, tasting Brunello and Rosso at two family-run wineries with lunch included.
Tue, Thu, SatDeparts 9:00 AM
Small group · Full dayA small-group day from Florence to Montepulciano, tasting Nobile wines and strolling Renaissance streets.
MondaysDeparts 9:00 AM
Small group · Full dayHunt white truffles near San Miniato, then taste organic Chianti Classico wines over a traditional truffle lunch.
Mon–SatDeparts 10:00 AMSee which tours still have room, then book in a few clicks. Planning ahead? Browse all upcoming dates →
Visiting Tuscany in a crowd of 30 to 50 travelers changes everything. Here is how our curated small groups ensure an authentic, unhurried wine country experience.
| Feature | Italy & Wine (Max 8 Guests) | Standard Commercial Bus Tours |
|---|---|---|
| Group size | Strictly 8 guests maximum in a dedicated minivan | 30 to 50+ passengers in a large coach bus |
| Wineries visited | Boutique, family-owned estates off the beaten tourist path | Industrial high-volume facilities built for bus crowds |
| Transportation | Air-conditioned minivans reaching hillside cellars & castles | Large coaches restricted to highways and perimeter parking |
| Lunch & tastings | Seated traditional multi-course lunch paired with reserve DOCG wines | Rushed standing tastings or self-paid cafeteria stops |
| Guide & attention | Expert English-speaking sommelier/guide with personal interaction | Tour chaperone with megaphone/audio headset commentary |
Unfiltered moments with our guests: rolling vineyards, subterranean oak barrel cellars, and relaxed winery lunches paired with regional wines.
A shared wine tour groups you with other travelers (max 8 guests) in a minivan, following a fixed itinerary and departure time from a set meeting point in Florence. A private wine tour reserves the vehicle, driver and guide exclusively for your party, with pickup available from your hotel or accommodation and an itinerary built around your preferences.
The best small-group wine tour in Tuscany depends on the wine region and the experience you would like to discover. Our guided small group tours each offer a different side of Tuscany:
Chianti Classico Wine Tour — ideal for iconic Tuscan reds, historic estates, olive groves and classic countryside landscapes.
Montalcino Wine Tour — best for Brunello di Montalcino lovers, with visits focused on one of Italy’s most prestigious wine regions.
Montepulciano Wine Tour — a great choice for Vino Nobile, medieval hill towns and a relaxed, authentic Tuscan atmosphere.
San Gimignano Wine Tour — perfect for travellers interested in Vernaccia, Tuscany’s celebrated white wine, alongside beautiful views and local food.
All tours are led by knowledgeable local guides, include carefully selected wineries and are kept intentionally small for a more personal and relaxed day. Choose the itinerary that best matches the wines and landscapes you would most like to experience.
Shared tours normally require a minimum of two participants.
If the minimum number is not reached, Italy and Wine may offer an alternative date, a similar tour, an upgrade to a private tour with an additional charge, or a refund of the amount paid.
The final confirmation is provided according to the conditions shown at the time of booking.
Shared wine tours are limited to a maximum of 8 guests traveling together in one minivan. This small-group format lets you meet fellow wine lovers while still enjoying a relaxed and personal day, with time to ask questions at the wineries, taste the wines and enjoy the Tuscan countryside.
Shared tours are an excellent choice for solo travelers, couples and small parties who would like to explore Tuscany without hiring a private vehicle. If you prefer to have the vehicle and itinerary exclusively for your own party, a private wine tour is the better option.
Yes. All guided tastings at boutique wineries, cellar tours with winemakers, and an authentic multi-course Tuscan lunch (or structured food and wine pairings) are fully included in every shared day tour.
All our small group tours depart from a convenient, easy-to-reach meeting point in Florence, just a short walk from Ponte alle Grazie and below Piazzale Michelangelo on the south bank of the Arno. Exact departure location details and a Google Maps pin are provided upon booking.
Yes. Our partner winery restaurants happily cater to vegetarian, vegan, and gluten-free diets, as well as specific food allergies. Please indicate your dietary requirements when completing your reservation.
Jeroen KoppenolNLD · 18 May 2026“We had a wine tasting tour guided by Andrea Colato. First of all, Andrea is really knowledgeable about all the differences in the wine-making. His enthusiasm made our day and tour. Then we experienced the beauty of Tuscany and Montepulciano. The view was breathtaking. Thank you very much / grazie mille!”Nobile di Montepulciano wine tour
Donald SchulteUSA · 30 September 2025“What a relaxing day out of the city, appreciating the great wines of Tuscany and the culture of San Gimignano. Matteo was an informative and fun guide to this region.”San Gimignano Wine Tour
Kate AndrewsUSA · 25 September 2025“Wonderful trip in Chianti region! Nicolo was a great tour guide!”Chianti Vineyard Tour
Bernadette ComstockUS · 22 August 2026“Matteo led our small group through a lovely day in Chianti — friendly, well-informed, and a pleasure to spend the day with.”Chianti Vineyard Tour
“A wonderful day exploring San Gimignano and visiting two wineries — Antonio was a fantastic host. The wines were exceptional, and the lunch was superb. Highly recommended, especially if you enjoy both red and white wines.”San Gimignano Wine Tour
Lisa RitchieUS · 11 June 2026“This tour is perfect for anyone who genuinely loves the winemaking process and its history. We planned our Italy trip around food and wine, and Montalcino was the region we most wanted to explore. It turned out we were the only ones booked that day, so it became a private outing with Niccolò — a WSET-certified guide with real depth of knowledge — joined by Ippolita, the owner's daughter. A wonderful, personal day from start to finish.”Brunello the Big Red Wine Tour
“A beautiful tour through some of the most enchanting wineries we have ever visited. Andrea made the entire day truly special with his warmth, knowledge, and thoughtful attention to every detail. From the stunning scenery to the memorable tastings, it was an experience we will always treasure.”Chianti & Super Tuscan Wine Tour from Florence
Lauren GrahamUS · 10 September 2026“Matteo and the winery hosts we met along the way were both knowledgeable and welcoming — a genuinely lovely day out. We would recommend it to anyone keen to learn more about Tuscan wine.”Chianti Rufina Castle and Villa Wine Tour
“The truffle hunting experience was an absolute highlight of our time in Tuscany. It was both fun and fascinating, with plenty of interesting details shared along the way about truffles, the local landscape, and the bond between the hunter and the dogs. The family who hosted us made us feel genuinely welcome from the very first moment—their warmth, passion, and hospitality turned the day into something far more personal than a simple activity. The estate and villa are beautiful, surrounded by peaceful countryside and full of Tuscan character. After the hunt, we enjoyed excellent food and wine, all prepared and served with great care. Every part of the day felt authentic, relaxed, and memorable. A truly special experience that we would wholeheartedly recommend to anyone visiting Tuscany.”Truffle Hunting & Wine Tasting
“Our Montepulciano wine tour from Florence was one of the highlights of our trip to Italy. Niccolò was an exceptional guide—knowledgeable, engaging, and genuinely passionate about sharing Tuscany’s history, culture, and wine traditions. The journey through the Tuscan countryside was as memorable as the wine tastings themselves. We visited welcoming, family-owned wineries in the Montepulciano region, where generations of winemakers have preserved their traditions while producing outstanding wines. Each vineyard offered a unique experience, with authentic hospitality, fascinating family stories, and exceptional local wines. This was much more than a wine tasting tour from Florence: it was a meaningful introduction to the people, culture, history, and traditions of Tuscany. By the end of the day, Niccolò felt more like a friend than a guide. Highly recommended for anyone looking for an authentic Montepulciano wine tour and a truly unforgettable day in Tuscany.”Nobile di Montepulciano wine tour
