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Top Picks for Castellina in Chianti Day tours

Q: How many Day tours are available in Castellina in Chianti on Trip.com?

Trip.com offers 596 Day tours in Castellina in Chianti

Q: What are the best Day tours in Castellina in Chianti?

From Siena: Day Tour in a Vintage Fiat 500 with Winery Private Tour in San Gimignano and Chianti Day Trip from Florence From Florence: Tuscany by Bike with Lunch and Wine Tasting

Q: What are the top-rated Day tours in Castellina in Chianti?

Siena: A Wine Tour and Tasting Experience Private Tour in San Gimignano Siena: 3h Private City Walking Tour with Optional Cathedral

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Discover 596 Day tours in Castellina in Chianti on Trip.com, updated November 9, 2025, with experiences lasting from 1 to 11 hours. Find the perfect adventure for your day!

From USD 10.87 per person, with an average total of USD 214.77. Choose the option that suits your plan.

With 663 verified reviews, Day tours Castellina in Chianti boast an average rating of 4.7.

This week's most popular Day tours: "Siena: A Wine Tour and Tasting Experience ", with 175 reviews and a 5 rating.

Now on Trip.com: "From Siena: Day Tour in a Vintage Fiat 500 with Winery", a 4-hour adventure in Castellina in Chianti!

The next available day tour departs on November 10, 2025. Book now to secure your spot!

Castellina in Chianti Day tours usually take about 4 hours — perfect for a relaxed, immersive experience!

5% of Castellina in Chianti Day tours now offer English-speaking guides

November is perfect for visiting Castellina in Chianti! Choose from Day tours available day tours, including seasonal hits like Siena: A Wine Tour and Tasting Experience .

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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596 Results for Castellina in Chianti Day tours

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󱩳Drive an original restored Fiat 500
From Siena: Day Tour in a Vintage Fiat 500 with Winery
Duration: 4 hrs
Italian
3.9/5
· 7 reviews
5% off
FromUS$283.54US$298.47
Private Tour in San Gimignano and Chianti Day Trip from Florence
Duration: 8 hrs
Italian
FromUS$199.36
󱩳Enjoy a light lunch and wine tasting in the countryside
From Florence: Tuscany by Bike with Lunch and Wine Tasting
Duration: 6.5 hrs
Italian
5% off
FromUS$164.85US$173.53
Siena Guided Tour with Cathedral and Optional Crypt & Museum
Duration: 2–3 hrs
Italian
4.4/5
Good· 60 reviews
FromUS$99.04
Siena: A Wine Tour and Tasting Experience
Duration: 3 hrs
Italian
5.0/5
Excellent· 175 reviews
FromUS$100.22
San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting
Duration: 11 hrs
4.5/5
Satisfactory· 155 reviews
FromUS$93.15
Lunch with Wine Tasting
Duration: 90 mins
Italian
4.8/5
Great· 74 reviews
FromUS$64.67
Private Tour in San Gimignano
Duration: 2 hrs
German
5.0/5
Excellent· 20 reviews
FromUS$330.13
Discover the Medieval Charm of Siena on a Private Walking Tour
Duration: 2–3 hrs
German
4.7/5
Great· 64 reviews
FromUS$347.82
󱩳Be transported back to the Middle Ages as you stroll through Siena
Siena: 3h Private City Walking Tour with Optional Cathedral
Duration: 3 hrs
Spanish
5.0/5
Excellent· 4 reviews
5% off
FromUS$318.71US$335.49
Highlights & Hidden Gems of Siena Private Tour - Duomo Included
Duration: 3 hrs
Italian
5.0/5
Excellent· 3 reviews
FromUS$433.89
󱩳Be inspired by tasting the wines and oils produced with love by the monks.
Tour with skip-the-line entrance to the Tuscan Abbey and final tasting
Duration: 2.5 hrs
Italian
5% off
FromUS$219.81US$231.38
Siena's Ultimate Food Tour: Full Tuscan Meal by Do Eat Better
Duration: 3 hrs
Italian
FromUS$107.30
󱩳Discover the magnificent Basilica of San Domenico and other historical buildings
Siena: Walking Tour and Skip-the-Line Duomo Tickets
Duration: 2 hrs
4.8/5
Great· 53 reviews
5% off
FromUS$43.96US$46.28
󱩳Enjoy an afternoon meal combining wine and seasonal culinary delights
Siena: Organic Winery Tour and Wine Tasting
Duration: 2.5 hrs
Italian
5.0/5
Excellent· 30 reviews
5% off
FromUS$82.43US$86.77
Guided Winery Tour and Wine Tasting in Siena
Duration: 150 mins
Italian
FromUS$88.18
󱩳Explore Florence, the cradle of the Renaissance, at your leisure
Florence: Full-Day Trip by High-Speed Train from Rome
Duration: 1 day
Spanish
5.0/5
Excellent· 4 reviews
5% off
FromUS$240.69US$253.36
Siena Medieval Power Quest: Self-Guided Family Feud Game
Duration: 60–90 mins
German
3.6/5
· 14 reviews
FromUS$10.87
󱩳Develop your knowledge of wine and winemaking techniques
From Livorno: Siena and Chianti Day Trip with Wine Tasting
Duration: 8 hrs
Spanish
5% off
FromUS$932.59US$981.68
󱩳The heart and soul of Siena, Piazza del Campo, the Gothic cathedral, and historic story treasures
Pisa & Siena & San Gimignano 1-day tour [Depart from Florence with admission ticket and lunch included]
Duration: 7.5 hrs
English
FromUS$134.14

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Frequently asked questions about Castellina in Chianti Day tours

How many Day tours are available in Castellina in Chianti on Trip.com?

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What are the best Day tours in Castellina in Chianti?

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What are the top-rated Day tours in Castellina in Chianti?

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How can I contact Trip.com customer support?

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Can I change or cancel my booking?

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How can I get discounted prices?

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Reviews/Trip Moments

★

Reviews:

Guest User2024-04-22

Very knowledgeable guide who took extra time to ensure we had the full experience within 3 hours. The additional tour of the underground frescoes and climb to the unfinished facade was a treat!

★

Reviews: Siena: A Wine Tour and Tasting Experience

Guest User2024-07-14

Maia is the best wine your guide you could ever have. We loved learning not only the wine-making process but the history of the land and the importance of the agriculture. We tasted so many delicious wines that the hardest part was deciding which to select. Not to mention the delicious lunch which could have been a Michelin star restaurant. Highly highly recommend!

★

Reviews: San Gimignano, Siena, Monteriggioni: Fully Escorted Tour, Lunch & Wine Tasting

Guest User2025-09-06

We had a great experience on this tour, thanks to our guide Jakopo and driver Raul. Jakopo was polite and very informative, sharing lots of interesting facts about Tuscany throughout the day. He also gave clear instructions about meeting points and times, which helped everything run smoothly. Raul, our driver, was equally professional and ensured we arrived safely at each destination. Our first stop was Monteriggioni, a charming little town where we had about 30 minutes—just enough time to grab a coffee and take in the atmosphere. We then spent around three hours in Siena, which felt like plenty of time to explore the historic streets, enjoy a delicious lunch at a local restaurant, and pick up a souvenir. After Siena, we stopped at Poggio ai Laghi for a wine tasting experience. We sampled four different wines, two types of balsamic vinegar, and a selection of bread and cold cuts—definitely a highlight of the day. Our final stop was San Gimignano, where we had 1.5 hours. While we enjoyed exploring this beautiful hilltop town, we would have loved a bit more time there, as it felt slightly rushed compared to the earlier stops. Overall, it was a well-organized tour with a good mix of cultural exploration, food, and relaxation. Highly recommended for anyone wanting to experience the best of Tuscany in a day.