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Top picks for Cortona Experiences

Q: How many Experiences are available in Cortona on Trip.com?

Trip.com offers 91 Experiences in Cortona

Q: What are the top-rated Experiences in Cortona?

Tuscany Hot Air Balloon Tour 1-day tour of Tuscany, Italy [Civita di Bagnoregio + Montepulciano + round-trip from Rome] Wine Tasting and Winery tour

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Discover 91 Experiences in Cortona on Trip.com, updated February 5, 2026, with experiences lasting from 1 to 12 hours. Find the perfect adventure for your day!

From CAD 10.82 per person, with an average total of CAD 114.80. Choose the option that suits your plan.

With 1.359k verified reviews, Experiences Cortona boast an average rating of 4.7.

This week's most popular Experiences: "Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines", with 581 reviews and a 4.7 rating.

Now on Trip.com: "Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena", a 9-hour adventure in Cortona!

The next available day tour departs on February 6, 2026. Book now to secure your spot!

Cortona Experiences usually take about 9 hours — perfect for a relaxed, immersive experience!

80% of Cortona Experiences now offer English-speaking guides

February is the perfect time to visit Cortona! Choose from Experiences available day tours, including seasonal favorites like Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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91 results for Cortona Experiences

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Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
Duration: 9 hrs
English
4.9/5
Excellent· 347 reviews
FromCAD 299.91
Montalcino: Brunello Wine Tasting Experience
Duration: 90 mins
English
4.4/5
Good· 45 reviews
FromCAD 54.17
Montepulciano: Wine Tasting & Lunch in a typical winery
Duration: 90 mins
English
4.1/5
Good· 24 reviews
FromCAD 91.64
Montalcino: Guided Winery Tour & Gourmet Food Tasting
Duration: 2.5 hrs
Italian
4.8/5
Great· 12 reviews
5% off
Limited-time sale
FromCAD 124.01CAD 130.54
Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines
Duration: 11–12 hrs
4.7/5
Great· 581 reviews
5% off
Limited-time sale
FromCAD 130.21CAD 137.07
From Siena: Chianti and Castles Tour with Wine Tastings
Duration: 5 hrs
Spanish
4.5/5
Satisfactory· 56 reviews
5% off
Limited-time sale
FromCAD 131.76CAD 138.7
Taste Umbria: Full Meal Walking Tour in Perugia by Do Eat Better
Duration: 3 hrs
Italian
FromCAD 148.30
Half-Day Tour of Italy's Chianti Wine Region|Includes 2 winery visits and wine tastings|Morning and afternoon available
Duration: 4 hrs
English
FromCAD 94.28
Tuscany Hot Air Balloon Tour
Duration: 3.5 hrs
English
5.0/5
Excellent· 5 reviews· 40 booked
FromCAD 432.78
1-day tour of Tuscany, Italy [Civita di Bagnoregio + Montepulciano + round-trip from Rome]
Duration: 9.5 hrs
English
5.0/5
Excellent· 2 reviews· 41 booked
FromCAD 214.12
Visit Best Wineries in Tuscany - Wine Tasting & Tour
Duration: 2 hrs
English
4.7/5
Great· 37 reviews
FromCAD 64.59
Order after consultation/Italy Sicili Palermo Catania Taormina Etna/airport/point-to-point car service/tour guide/driver/private car service
English
FromCAD 90.58
Florence Trattoria Marione restaurant reservation service
English
FromCAD 10.82
Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area
Duration: 2 hrs
English
4.9/5
Excellent· 91 reviews
FromCAD 66.23
Wine Tasting and Winery tour
Duration: 2 hrs
English
5.0/5
Excellent· 37 reviews
FromCAD 57.96
Enjoy and Taste the Flavors of Wine in an Open-air Venue
Duration: 1 hr
English
4.9/5
Excellent· 29 reviews
FromCAD 41.67
La Hora Feliz viral Italian restaurant in Milan - restaurant reservation service
English
FromCAD 10.82
Private Tuscan meal with Wine and EVO oil tasting
Duration: 90 mins
English
4.8/5
Great· 21 reviews
FromCAD 91.08
Montefioralle Winery - Tour and Wine Tasting in Chianti
Duration: 75 mins
English
4.3/5
Good· 40 reviews
FromCAD 58.33
Best Winery with Restaurant and wine tasting from Florence
Duration: 90 mins
English
4.9/5
Excellent· 32 reviews
FromCAD 82.80

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Reviews/Trip Moments

★

Reviews: Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Guest User2024-10-01

Marco was our guide and he was excellent. 5/5 for him. First vineyard explained all the regulations around the brunello di montalcino wines as well as tasting with some bruschetta, in a lovely setting. The second stop was for lunch which was fantastic, cooked by the owners wife. There were further wine tastings with lunch, however there was no look around their winery. There was a very short stop (25 minutes) to briefly look around Montalcino then a stop at the third vineyard. This tour showed the winery then some small tastings. There is sales pitch, understandably, at each location and we did buy 6 bottles overall, ranging from 68 to 120 euros. It was lovely to be on such a small and intimate tour and meet lovely people as part of it. However I would suggest reducing to two vineyards and more time to explore Montalcino.

★

Reviews: Montalcino: Brunello Wine Tasting Experience

Guest User2025-11-12

A magnificent castle built in 1441. A wonderful historical tour narrated by Alicia, who was eloquent and captivating. A modest place, yet so rich in culture. Thank you, Alicia, for this superb tour and captivating narration!

★

Reviews: Montepulciano: Wine Tasting & Lunch in a typical winery

Guest User2025-09-14

Very good tour of winery, in-depth interesting detail of wine making process; food was good. Only caution, the city is difficult to find parking, usually outside the city walls, plan on extra time to find parking and walking is uphill.

★

Reviews: Montalcino: Guided Winery Tour & Gourmet Food Tasting

Guest User2025-11-03

guide was very knowledgeable and very friendly. we had a wonderful time touring vineyards and got to see the grapes being pressed. The wine tasting was superb and we bought a big bottle to drink on our first anniversary

★

Reviews: Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines

Guest User2026-01-22

Thank you so much to our wonderful guide, Anna, for a wonderful day in Tuscany. The tour was very interesting, the pace and choice of locations were perfect. We really enjoyed the stop at the store with wonderful delicacies, sweets, and Tuscan wines. Beautiful Montepulciano will remain in our hearts forever. The lunch was wonderful, very tasty, and the wine tasting was wonderful. We were very pleased with the organization of the trip; everything was simply perfect!

★

Reviews: From Siena: Chianti and Castles Tour with Wine Tastings

Guest User2026-01-14

Thanks to our friendly and informative guide Tsvetelin we had a lovely relaxed day. Would recommend this tour to visit both the villages and for the wine tasting.

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