The verdict
Our pick
Val d'Orcia: Brunello & Montepulciano Wine Day Trip★ 4.66 (405) · 10h 30m
Best price
Montalcino: Olive Oil Mill Tour & Tasting with Local Producer★ 4.98 (139) · 1h 30m
Top rated
Private Cheese and Wine Tour from Siena: Pienza, Montalcino★ 5.00 (41) · 8h
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Private experiences (3)
Montalcino & Montepulciano: Brunello Wine Tour from FlorenceYou get picked up from your Florence hotel and driven through Val d'Orcia to Montalcino and Montepulciano, where you taste Brunello and Nobile wines directly from producers. The route includes Pienza for a Pecorino cheese tasting and a walk through its Renaissance streets. Lunch and all transport are included, and you return to Florence in the evening without arranging anything yourself.Is it for me?Book this if you want to taste Brunello and Nobile wines where they're made without arranging your own transport or winery contacts—the producer meetings and small-group format are what make a day in Montalcino and Montepulciano feel like an insider's visit instead of a standard wine route.
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.
Montalcino & Chianti: Private Wine Tasting Small Group TourYou spend the morning walking Montalcino's fortress and learning why Brunello di Montalcino commands its price, then taste wines at two small wineries chosen for what you're interested in. The private group format means no crowds and no fixed schedule — your guide adjusts based on how long you want to stay at each stop. You leave with two tastings included and a real sense of how the region's soil and tradition shape what's in the glass.Is it for me?Book this if you want to taste real Brunello and Chianti without the standard tour-group experience — the private format and small winery selection mean your guide can actually respond to what you're curious about instead of moving everyone through the same stops.
Half day and longer (3)
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.
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.
Florence: Chianti Wine Tasting & Montalcino Day TripYou're picked up from your Florence hotel and driven through Chianti vineyards for a morning wine and oil tasting, then to a working farmhouse near Montalcino for a guided lunch with local wines and regional food, followed by walks through the medieval villages of Montalcino and Montepulciano, with return to Florence by evening. The minivan holds eight people maximum and includes WiFi, so you're not crammed in, and the driver handles all the navigation and timing.Is it for me?Best for travelers based in Florence who want to see the main Tuscan wine villages and taste wines at source without renting a car or arranging their own transport and timing—the fixed schedule and included lunch mean you show up at your hotel and the rest is handled.
Montalcino Tours — what to know before booking
This guide compares 9 bookable options for Montalcino Tours, with up-to-date prices and real traveler reviews. Prices start at € 70. The average rating is 4.8 out of 5, based on 899 traveler reviews.
Most options last half a day or longer. 9 of the 9 options offer free cancellation. 3 private experiences are also available for closed groups. The verdict at the top highlights the travelers' favorite, the best price and the top-rated option, updated with live data.
Frequently asked questions
How much does Montalcino Tours cost?
Prices start at € 70. There are 9 options to compare, and the final price depends on the date, group size and the option you choose.
Can I book with free cancellation?
Yes: 9 of the 9 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.
Which one is the travelers' favorite?
Val d'Orcia: Brunello & Montepulciano Wine Day Trip is the travelers' favorite, rated 4.7 out of 5 across 405 reviews.
Are private options available?
Yes, 3 private experiences are available if you prefer a closed group.
