The verdict
Our pick
Siena: Brunello di Montalcino Wine Tour & Tuscan Lunch★ 4.93 (1,030) · 9h
Best value
Tuscany: Wine Tasting Near Siena with Local Foods & Terrace Views★ 4.89 (81) · 1h 30m
Top rated
Montalcino: Brunello Cooking Class & Winery Tour with Lunch★ 4.99 (328) · 4h
The 12 best-value of 16 options, side by side
✓ 2026-09-29Real price per person across the 16 options: € 28–€ 259 (median € 85). With 100+ reviews: 9 of 16.
Default order: real price per person — the group price divided by the seats it includes.
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Private experiences (3)
Siena: Underground Wine Tasting in Private Medieval CaveYou’ll step through an unmarked door near San Domenico into Siena’s oldest underworld for a private wine tasting led by a local sommelier. Taste Brunello di Montalcino, Chianti Classico, and Super Tuscan wines inside an Etruscan-era cave with only a handful of guests. Expect stories, laughter over local cheese, and that rare feeling of being let in on something secret.
Private Cheese and Wine Tour from Siena: Pienza, MontalcinoA private full-day tour from Siena takes you south through the Val d'Orcia to an organic dairy farm for cheese and olive oil tasting, then to the Renaissance town of Pienza for lunch at your own pace, and finally to Montalcino for a winery tour and tasting of Rosso and Brunello di Montalcino wines. Your English-speaking guide picks you up from your hotel and handles all driving; the route covers eight hours and includes all tastings and farm access.Is it for me?Book this tour if you want to taste food and wine where it is made rather than in a restaurant, and you prefer traveling as a private group instead of joining others. The eight-hour day is built around the farm and winery visits, so the tastings and cellar tour are the focus, not a quick stop between other sights.
Private Brunello di Montalcino Wine Tour with Local SommelierIf you want to taste real Brunello wines right where they’re made—and see what makes this part of Tuscany so special—this tour’s got it all: local stories, small-batch wineries, and plenty of time to soak up Montalcino’s charm.
Up to 2 hours (2)
Florence / Tuscan Wine School: Tasting Class with Local PairingsStep into a cozy Florence classroom where you’ll taste classic Tuscan wines like Chianti and Brunello alongside local cheeses, meats, and olive oil. Learn pairing tips from a friendly local guide and hear stories behind each bottle. You’ll leave with new favorites—and maybe a few laughs—that stick with you long after you’ve left Tuscany.
Montalcino Brunello Wine Tasting & Lunch in a CastleMontalcino wine tasting and lunch combines three local wines — including Brunello di Montalcino — with a three-course Tuscan meal served in a medieval castle. A professional sommelier leads you through the vineyard, explains the winemaking methods, and guides the tasting; the experience runs about 90 minutes and includes a tour of the property. English and Italian options are available, and vegetarian lunch is an option at checkout.Is it for me?Book this if you want to taste Brunello where it is made and understand how, rather than just sample wines in a tasting room — the sommelier's walk through the vineyard and the castle grounds is what sets this apart from a standard wine bar visit.
2 to 5 hours (3)
Siena: Organic Wine Tour & Tasting with Tuscan LunchYou’ll walk Siena’s countryside vineyards with a local guide who knows every vine by heart. Taste organic wines straight from the source in their cellar, then sit down to a light Tuscan lunch made from seasonal ingredients—all just minutes from medieval Siena. Expect real stories, real flavors, and maybe even a laugh or two you’ll remember later.
Siena walking tour with lunch & Chianti wine tastingA 2.5-hour walking tour of Siena led by a licensed English-speaking guide, moving through medieval neighborhoods, historic piazzas and hidden streets to taste gelato, wine and a full lunch of homemade pici pasta, pecorino cheese and Chianti. The tour keeps to small groups of no more than 12 people and includes an awarded gelato shop, wine tasting near Piazza del Campo, and a meal at a traditional osteria.Is it for me?At 2.5 hours, this tour fits into a morning or afternoon without consuming your whole day, which means you can pair it with other Siena plans or simply move on to another town by evening. The small group size and licensed guide make it work for families with young children and for travelers who want actual conversation about the places you're walking through, rather than a rushed procession through checkpoints.
Organic Wine Tasting in Siena: Vineyard, Cellar & 5 WinesA guided winery tour and tasting near Siena where you walk the organic vineyard, explore the cellar to understand winemaking at each stage, then taste five wines paired with seasonal Tuscan products and olive oil. The experience runs 2.5 hours and includes a light afternoon meal, parking and a guide in English or Italian. Minimum age is 18.Is it for me?The 2.5-hour length fits neatly into an afternoon without eating up your whole day in Siena, so you can combine it with time in the medieval town or other plans. If you want to understand wine beyond the taste—the soil, the process, the reasoning—this tour builds that knowledge as you go.
Half day and longer (5)
Siena & San Gimignano: Medieval Towns, Chianti Wine & LunchYou visit four medieval towns—San Gimignano, Monteriggioni, Siena—and a Chianti winery, all in one day with transport, a three-course lunch, wine tasting, and an English-speaking guide included. The pace is set; you just show up at the Florence meeting point and let the coach and the escort handle the logistics.Is it for me?Choose this tour if you want the main Chianti and medieval Siena highlights in a single day without arranging transport, winery bookings, or timing yourself—the fixed schedule and English-speaking guide mean you arrive at Florence, get on the coach, and everything else is handled.
Val d'Orcia wine tour from Siena: Brunello and Nobile tastingsA full-day wine tour from Siena through Val d'Orcia visits three towns—Montepulciano, Pienza and Montalcino—with two wine tastings, lunch with cured meats and pasta, and free time to walk each town's historic streets. A multilingual guide leads the group by minivan, and wine tastings are held in English with translation support when needed. The tour runs 10 to 11 hours and departs from Siena Railway Station.Is it for me?Pick summer for warm weather and outdoor tastings, or winter for fewer crowds—both visit the same wineries and include tastings in Pienza and Montepulciano with lunch included.
Brunello di Montalcino Wine Tour: 2 Wineries with Pairing LunchA full-day wine tour in Montalcino takes you to two boutique Brunello wineries for tastings and a cellar tour, then to a pairing lunch at the second winery featuring local specialties. Hotel pickup and drop-off are included, along with an English-speaking driver-guide and a small group capped at 8 guests. The day also includes time to walk the medieval fortress and artisan shops of Montalcino itself.Is it for me?Hotel pickup means you don't need a car or a ride to the wineries—the driver collects you and handles the route, timing and navigation for the whole day, which settles the logistics if you're staying in town without transport or arriving by train.
Chianti Castles & Wine Tasting Day Trip from SienaYou’ll walk castle paths above Chianti vineyards, taste wines poured by people who make them, share lunch at a Tuscan estate, and wander through medieval villages—all with a local guide who knows every shortcut and story. It’s not just tasting wine; you’ll feel part of this sun-baked landscape for a day.
Brunello di Montalcino Wine Tour from Siena: 2 TastingsA wine tour from Siena to Montalcino with guided tastings of two Brunello di Montalcino wines at local estates, a professional multilingual guide, and free time to walk the medieval fortress town. The tour includes a scenic drive through Val d'Orcia vineyards, insight into Brunello aging traditions, and a light Tuscan snack with fresh bread and olive oil. Groups stay under eight in a minivan or up to thirty in a minibus, and the full day runs 5.5 hours from Siena Railway Station.Is it for me?Book this tour if you want to taste Brunello in the cellars where it's aged rather than in a hotel tasting room, and if you have a free afternoon from Siena — the 5.5-hour round trip leaves room for an early start or a late dinner back in the city. The small group size and English-speaking guide make it straightforward for first-time visitors to Montalcino, and the free time in the town means you're not locked into a schedule if you want to linger at a winery or explore on your own.
Frequently asked questions
Can I book with free cancellation?
Yes: 16 of the 16 options offer free cancellation, so you can book now and confirm your plans later.
How long do these experiences last?
Most options last half a day or longer. There are also shorter and longer formats to fit your itinerary.
Which one is the travelers' favorite?
Siena: Brunello di Montalcino Wine Tour & Tuscan Lunch is the travelers' favorite, rated 4.93 out of 5 across 1,030 reviews.
Are private options available?
Yes, 3 private experiences are available if you prefer a closed group.
