What to do and see in Castellina In Chianti, Tuscany: The Best Cultural Tours

December 5, 2021 Oliva Fomby

An ancient town of just under 3,000 between Florence and Siena, picture-perfect Castellina In Chianti is set in the wine-famous Chianti Hills. The many wonderful sights include the imposing 14th-century Rocca (Fortress), offering spectacular views of the town and surrounding countryside, the 16th-century San Salvatore church and the Via delle Volte medieval arched passageway. Just outside of town are the pre-Roman Etruscan burial tombs of Monte Calvario and the Necropolis of Poggino.
Restaurants in Castellina In Chianti

1. Private Tuscany Wine Tour Experience from Florence

Cooltours - Day Tour
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5.0 based on 31 reviews

Private wine tour experience to visit Tuscany's best wineries, to sample top end wines and have an educational and tasty food & wine pairing session to combine each wine to each food speciality. A full day escorted by a friendly professional driver-guide, specialized in wine-making and sommelier, fluent in English and knowledgeable about the history of the area.

Inclusions: All taxes, fees and handling charges, Lunch, Wine tasting, Driver/guide, Transport by air-conditioned minivan, Hotel pickup and drop-off

Exclusions: Gratuities

Reviewed By PaolaMarieShep

Spent a fabulous day with Anna on 13th October 2020. Visiting 3 vineyards, Anna is very knowledgeable and a great host we were made very welcome everywhere, following COVID requirements of course. We cannot recommend Anna highly enough!

2. Chianti Dreaming: Private Boutique Winery and Hilltop Village Tour

Caf Tour & Travel
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5.0 based on 2 reviews

Have a slow and fascinating Chianti Experience! Discover in total comfort all the charm of the most beautiful countryside in the world and experience its culture, history and traditions, walking along the ancient streets of a picturesque Medieval village. Savor the best local flavors through a scrumptious wine tasting in an enchanting winery, surrounded by a breathtaking scenery!

Inclusions: Pick-up and drop-off at the hotel in Florence if centrally located, Transport by deluxe air-conditioned vehicle with WIFI on board, English/Italian speaking driver, Delicious tasting of three excellent wines and typical products, in a small-scale production winery., Stop in Greve in Chianti and in a second winery (wine tasting with 4 wines) if option selected

Exclusions: Gratuities, Guide Service, Everything not mentioned as Included

Reviewed By aakebe

Only 7 people and the tour was by Van. The driver guided us during the drive but no guide joined us at our stop in Castellina. Professional presentations at the wineries. Especially at Poggio Amorreli with Andrea where we were treated with Spumante, one white and two red Chianti and one supertuscan. We also got bread, cheese, salami with their own balsamic vinegar and olive oil. The driver called for a taxi upon arrival in Florence ????

3. Montalcino and Montepulciano Private Tour

Tuscany Private Tour, Via, Viale IV Novembre, 35, 53011 Castellina in Chianti SI, Italy Tuscany Private Tour
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5.0 based on 1 reviews

Travelling in Val d'Orcia is an unforgettable experience. Your eyes become dazzled by the beauty of the colours of this land, unsurprisingly a UNESCO World Heritage Site. This tour has been created for you to discover the most painted corner of Tuscany, made of enchanted landscapes, tree-lined avenues. Sunrises and sunsets of extraordinary, unique colours in the world are one great addition when wandering the road from Montepulciano to Montalcino through Pienza, considered one of the most amazing routes of Italy.

Inclusions: Visit of Montepulciano, Typical tuscan lunch + wine tasting + visit of a winery, Visit of Pienza, Visit of Montalcino + winery visit and wine tasting, About 6 hours tour, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By 628brendah

What an amazing day! It started with truffle hunting with Roberto and his two dogs - Ori and Chloe! We learned a lot about truffle hunting and how the dogs are trained. Chloe was 'in training' and it was fun to see how Roberto used both dogs. They found about 12 truffles in all of various sizes! Then we headed to a small family winery where we ate the fruits of our labor!!! We had a 4 course 'absolutely delicious' meal, tasted a lot of great wines, in addition to olive oil and honey! We even bought a bottle of wine to take with us and watched Sylvia add the DOCG label by hand (which are closely tracked by the region)! We had a great tour guide, Paelo, with us the entire day! He picked us us at our farmhouse, was our translator when needed, was very courteous and informative! I would highly recommend this very unique experience! And I would recommend Tuscany Private Tours. They were very easy to communicate with and very responsive!

4. Grape stomping in Tuscan farmhouse from Siena

Basilica Cateriniana San Domenico, Piazza San Domenico, 1, 53100 Siena SI, Italy Tuscany Private Tour
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5.0 based on 1 reviews

Stomp on grapes in a small winery in the beautiful Chianti hills. Experience the feeling of grapes under your feet and discover the secrets of winemaking during your 4-hour tour with English-speaking guide. Enjoy a homemade lunch with a wine-tasting session at a 200 year old villa. Visit its ancient wine cellar. (From late August to mid September, grape picking is also involved on request).

Inclusions: Professional guide, Local guide, Wine-tasting, Lunch

Exclusions: Gratuities

Reviewed By 628brendah

What an amazing day! It started with truffle hunting with Roberto and his two dogs - Ori and Chloe! We learned a lot about truffle hunting and how the dogs are trained. Chloe was 'in training' and it was fun to see how Roberto used both dogs. They found about 12 truffles in all of various sizes! Then we headed to a small family winery where we ate the fruits of our labor!!! We had a 4 course 'absolutely delicious' meal, tasted a lot of great wines, in addition to olive oil and honey! We even bought a bottle of wine to take with us and watched Sylvia add the DOCG label by hand (which are closely tracked by the region)! We had a great tour guide, Paelo, with us the entire day! He picked us us at our farmhouse, was our translator when needed, was very courteous and informative! I would highly recommend this very unique experience! And I would recommend Tuscany Private Tours. They were very easy to communicate with and very responsive!

5. Off-Road Wine Tour in Chianti from Florence

Piazzale di Porta Romana, 50125 Firenze FI, Italy Tuscany Private Tour
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5.0 based on 3 reviews

People who love being immersed in the nature and wish to discover Chianti will love this experience we have created. This excursion will also take you to the best wineries of the area, known for its incredible photo-inspiring landscapes and cozy, classic architecture, today mixed with the best techniques. Chianti produces some of the most celebrated red wines in the world. You will have a chance of a deep, confidential chat with wineries owners and a great meal will follow, naturally. This is more than ‘dining in Tuscany’, this is going to the roots of Tuscany through its most precious ingredients and traditions. The first cellar produce of 1000000 bottles a year. The second is an historic cellar from 15°C. that produce about 150000 bottles. The third, where you will also have lunch, is a family-run wine cellar where they also make: extra virgin olive oil, honey and jams. Their wine production is about 15000 bottles with 101 years old grapevines.

Inclusions: All taxes, fees and handling charges, 15 wine tastings, 3 winery visits, Driver/guide, Lunch, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By S B

This was a magical experience, we will remember it forever! My girlfriend and I were staying in Castiglione della Pescaia and didn't have a car, so at Tuscany Private Tour they tailored the whole program to our needs. They sent Filippo to pick us up from right below our airbnb, and he took us to different vineyards and borghi in the area and told us about the history of these places. He was extremely professional but also very friendly and receptive to our needs. He told us he also organises tours of Tuscany by bike and this is something we will definitely consider doing with him in the future. We would highly recommend him and the agency if you want to experience something special that you won't forget.

6. Off-Road Tuscan Wine Tour from Castellina

Viale IV Novembre, 35, 53011 Castellina in Chianti SI, Italy Tuscany Private Tour
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4.9 based on 11 reviews

Off road wine tour is a new way to visit the Chianti Valley. 3 wine cellers, Vintage SUV, typical tuscan lunch and 15 wine tastings, honey tasting, olive oil tastings, professional tour guide.. ALL INCLUDED!

Inclusions: Driver-guide, Lunch, Wine tasting, All taxes, fees, and handling charges, GST (Goods and Services Tax), Fuel surcharge

Exclusions: Gratuities

Reviewed By S B

This was a magical experience, we will remember it forever! My girlfriend and I were staying in Castiglione della Pescaia and didn't have a car, so at Tuscany Private Tour they tailored the whole program to our needs. They sent Filippo to pick us up from right below our airbnb, and he took us to different vineyards and borghi in the area and told us about the history of these places. He was extremely professional but also very friendly and receptive to our needs. He told us he also organises tours of Tuscany by bike and this is something we will definitely consider doing with him in the future. We would highly recommend him and the agency if you want to experience something special that you won't forget.

7. Private Tour: Siena, San Gimignano and Chianti Day Trip from Florence

Chianti Drivers
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4.9 based on 48 reviews

*Experience for your private party* Explore the art, culture and medieval history of Italy on this private 8/9-hour tour. Discover the delights of Tuscany on a private day trip from Florence. With a knowledgeable English-speaking private driver, travel through the renowned Chianti wine region to visit the towns of Siena, the fortress of Monteriggioni and San Gimignano. See world-famous landmarks like Siena’s Piazza del Campo, home to the annual Palio horserace, and the medieval hilltop towers of San Gimignano. • Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available at any needs. * With agreements during the reservation we can organize lunch in wine cellars or in the farms. This is a highly recommended experience, especially for the wine lover.

Inclusions: Hotel pickup and drop-off in Florence, Private luxury minivan, Bottled water, Onboard Wi-Fi (on request at reservation), Our drivers are all extremely familiar with Tuscany and with the main destinations in Italy. They will always share information, curiosities and traditions about the area of the sightseeing and they are available at any needs., Spanish-, Portuguese- or French-speaking driver upon request

Exclusions: Lunch in winery or farm. (to decide at the time of briefing in the morning with your driver), Guide city tour (you will find the complete tour with private guide in Siena on viator with this code 23322P50)

Reviewed By Laurettab1974

We had a fab day! Our driver, Massimo was great! Very engaging, informative and made so enjoyable trip. Satisfied and exceeded our expectations Not only the tour through Tuscany was beautiful and the wine delicious, but above all Max made the whole experience unique! I recommend ChiantiDrivers to anyone! I highly recommend it.

8. Chianti Wine Tasting and San Gimignano Day Trip from Siena

Viale Vittorio Veneto, 27, 53100 Siena SI, Italy My Tour in Italy
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4.5 based on 203 reviews

Spend an afternoon in Tuscany, visiting the small town of San Gimignano, on a half-day tour from Siena. Hear the history of the region from an expert guide, and then enjoy some free time to explore the medieval hill town of San Gimignano, discovering sites like Piazza del Duomo and Via Francigena. Then, travel to the heart of the Tuscan hills for a tour of a winery estate, where you'll learn about Tuscan wine, and enjoy a wine-tasting session, too!

Inclusions: Air-conditioned vehicle, Vineyard tour and wine tasting session, Snack with sliced cold meat and typical salami, Wine, oil and balsamic vinegar tasting, Visit of San Gimignano

Exclusions: Gratuities, Hotel pickup and drop-off

Reviewed By Oversunsetplain

I couldn’t put correct date on this review - I did this tour with my two children in August 2019 and originally posted it then. I have had a message to say that I had posted it under the wrong company (one with a very similar name). I would like to re-post the review as we had such a brilliant day with our guide and would like to recommend the tour company to others whenever this type of activity goes ahead again! Our guide Ms Ivanova was very knowledgeable and friendly. The tour took in many places around the city and we also visited the Uffizi in the afternoon. I was with my children aged 6 and 9 and both really enjoyed this day. They felt included and learned a lot. The guide met us at the times planned and gave plenty of opportunities for questions and were able to answer any queries. Everything was organised well and went smoothly. We were unable to book a tour inside the Duomo but actually this one which took us all the way around the outside and to other fascinating parts of the city was perfect for my family.

9. 500 Vintage Tour: Chianti Roads Experience with Lunch from Florence

Via Elio Gabbuggiani, 7, 50144 Firenze FI, Italy My Tour in Italy
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4.5 based on 15 reviews

Experience the Tuscan countryside by vintage Fiat 500 on an 5-hour scenic driving tour. Stop for a light lunch at a Chianti winery and marvel at medieval villages in the rolling hills of the famous wine region.

Inclusions: Transportation to Chianti Area, Professional tour leader, Original restored Fiat 500 (manual gear box), Light lunch

Exclusions: Hotel pickup and drop-off

Reviewed By Oversunsetplain

I couldn’t put correct date on this review - I did this tour with my two children in August 2019 and originally posted it then. I have had a message to say that I had posted it under the wrong company (one with a very similar name). I would like to re-post the review as we had such a brilliant day with our guide and would like to recommend the tour company to others whenever this type of activity goes ahead again! Our guide Ms Ivanova was very knowledgeable and friendly. The tour took in many places around the city and we also visited the Uffizi in the afternoon. I was with my children aged 6 and 9 and both really enjoyed this day. They felt included and learned a lot. The guide met us at the times planned and gave plenty of opportunities for questions and were able to answer any queries. Everything was organised well and went smoothly. We were unable to book a tour inside the Duomo but actually this one which took us all the way around the outside and to other fascinating parts of the city was perfect for my family.

10. Grape stomping in Tuscan farmhouse

Viale IV Novembre, 35, 53011 Castellina in Chianti SI, Italy Tuscany Private Tour
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4.0 based on 1 reviews

Stomp on grapes in a small winery in the beautiful Chianti hills. Experience the feeling of grapes under your feet and discover the secrets of winemaking during your 4-hour tour with English-speaking guide. Enjoy a homemade lunch with a wine-tasting session at a 200 year old villa. Visit its ancient wine cellar. (From late August to mid September, grape picking is also involved on request).

Inclusions: Private tour, Professional guide, Wine-tasting, Lunch, All taxes, fees and handling charges, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By 628brendah

What an amazing day! It started with truffle hunting with Roberto and his two dogs - Ori and Chloe! We learned a lot about truffle hunting and how the dogs are trained. Chloe was 'in training' and it was fun to see how Roberto used both dogs. They found about 12 truffles in all of various sizes! Then we headed to a small family winery where we ate the fruits of our labor!!! We had a 4 course 'absolutely delicious' meal, tasted a lot of great wines, in addition to olive oil and honey! We even bought a bottle of wine to take with us and watched Sylvia add the DOCG label by hand (which are closely tracked by the region)! We had a great tour guide, Paelo, with us the entire day! He picked us us at our farmhouse, was our translator when needed, was very courteous and informative! I would highly recommend this very unique experience! And I would recommend Tuscany Private Tours. They were very easy to communicate with and very responsive!

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