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

October 17, 2021 Agatha Simes

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. Dinner in the Vineyards from Siena

53100 Siena, Province of Siena, Italy My Tour in Italy
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5.0 based on 4 reviews

Enjoy a magical evening in the Chianti region and live the unforgettable experience of a dinner in the vineyards. Start off by visiting the farm’s wineries and tasting some delicious wines, after which you’ll and enjoy an outdoor barbecue accompanied by music and a delightful atmosphere.

Inclusions: Travel by GT coach or minivan with, Expert multilingual tour leader, Visit of the estate’s wineries on a wine route inside the estate with tasting of wines, Dinner in the vineyards, Dinner, Alcoholic Beverages

Exclusions: Pickup and Dropoff, Gratuities

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.

2. Private The Essence of Tuscany: Chianti Classico, Montalcino, Montepulciano

Caf Tour & Travel
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5.0 based on 1 reviews

Following the scent of the Great Wines through the most stunning landscapes of Chianti, Val d’Orcia and Val di Chiana

Inclusions: Pick Up and Drop Off at the hotel in Florence if centrally located, Transport by deluxe ari-conditioned vehicle with WIFI on board, English/Italian speaking driver, Typical Tuscan Lunch in a family run Farm, Wine and Food Tasting with 3 wines and local products in a cozy Winery

Exclusions: Gratuities, 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. VESPA Tour in Tuscany

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 4 reviews

Nothing speaks ‘romanticism’ more than a tour on a Vespa, a ride through history and style, that can really change the tone of your holiday. The Vespa experience offers an original take on touring Tuscany, while we take care of each and every detail. Leave chaos behind you, enjoy the best of Tuscany’s landscapes from your Italian Vespa and skip traffic like Italians do. Discover the beautiful Tuscan hills riding a Vespa scooter. Visit three quaint villages during your 6-hour tour with English-speaking guide. Enjoy a homemade lunch with a wine-tasting session in our organic farm. Visit its ancient wine cellar.

Inclusions: Lunch, Wine tasting, All activities, Tour escort/host, Hotel pickup and drop-off (selected hotels only), Use of helmet, Private tour, 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.

4. 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.

5. Horseback Riding Tour with wine tasting from Siena

Tuscany Private Tour
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5.0 based on 1 reviews

Getting in tune with such an intelligent animal like a horse is rejuvenating for body and soul: cross the Chianti countryside paths led by an expert guide, admire those world famous hills covered by olive groves and vineyards and get in tune with nature, your horse and yourself. Highlights: • Private tour for couple and small groups • Departure from an agreed meeting point or from your hotel at 9:30 am • Horse riding between vineyards and olive groves • Transfer by car to the winery where the experience takes place • Tuscan meal + 4 wine tastings • Return to our agreed meeting point or drop off to your hotel • Languages: Italian, English + French and Spanish on request

Inclusions: Lunch, Wine tasting, Professional guide, Tour escort/host, Use of helmet, Horse riding, 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!

6. PRIVATE Full-Day Siena, San Gimignano and Chianti from Florence

UniqueTuscany private Tours
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5.0 based on 27 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • With this fascinating tour you will discover a unique part of Tuscany in a private day-trip from Florence. With an expert local driver/guide, immerse yourself in the renowned Chianti wine region and explore the cities of Siena and San Gimignano. You will tour historic landmarks such as Piazza del Campo in Siena, home to the annual Palio, and the medieval towers of San Gimignano. Add an optional, unforgettable lunch to savor traditional Tuscan wines and specialties in a local organic farm or winery! • 8/9-hr Full-Day private tour of Tuscany • Visit the medieval cities of Monteriggioni, San Gimignano and Siena • Hear live commentary of the wine cellars by your guide • Taste Craft Chianti Classico wine at a local vineyard • Pick-up and drop-off at your Hotel or at the address provided • Travel in a Mercedes-Benz minivan

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes-Benz MiniVan, Air-Conditioned, English-speaking licensed driver, Free time in Siena and San Gimignano, Unlimited cold mineral water , On-Board WiFi

Exclusions: Local guides in Siena and San Gimignano, Lunch in farm or winery available at an extra cost 25€pp to 50€pp, depending on option chosen, Entrance fees (Cathedral of Siena ia approx. 7€ pp.)

Reviewed By Gabriel S

This was our 2nd private tour that we did through Uniquetuscany (2017/2020). Our guide, Alessandro was very specific to the covid restrictions and offered us new masks during the day! He did a wonderful job explaining the history of the towns. Our highlight was the visit to Tuscany organic farm where we had our lunch with amazing view. We stopped at Siena, San Gimignano and Pisa. There was a lot of walking and moving from in and out of the minivan so make sure you wear comfortable shoes. I definitely recommend this tour while visiting Florence since you get a lot of history while on the minivan to each town. Just not enough time in all the towns but 10 hours is a long day! still worth the trip! Highly recommended..

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 and Castle Tour from Siena

53100 Siena, Province of Siena, Italy My Tour in Italy
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4.6 based on 43 reviews

Discover the beauty of the Tuscan countryside on this 5-hour tour. Visit two wineries and learn about the process of wine-making. Enjoy a variety of tasting opportunities including wine and oil. Spend free time in the medieval village of Monteriggioni.

Inclusions: Hotel pickup and drop-off, Travel by air-conditioned minivan, Expert multilingual guides, Wine, oil and balsamic vinegar tasting, Snack (sliced cured meats and salami), Visit of an ancient Castle

Exclusions: Gratuities

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. Vintage Fiat 500 Tour from Siena: Tuscan Hills and Winery Lunch

Piazza Gramsci, 53100 Siena, Province of Siena, Italy My Tour in Italy
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4.5 based on 22 reviews

Experience the beauty of Tuscany in style while driving a vintage Fiat 500, the most classic Italian car. After hotel pickup from Siena, start in Monteriggioni and cruise through the gorgeous hills of Chianti, stopping at a local winery for a wonderful Italian lunch with wine. You’ll follow your guide in a caravan, with two adults per car. Numbers are limited to 10 on this full-day small-group tour, ensuring a more personalized experience.

Inclusions: Vintage Fiat 500 car to drive during tour, Tour escort/host, Winery tour, 3-course lunch, Tasting of different wines, water, Hotel pickup and drop-off by minivan

Exclusions: Gratuities

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. Private Vip Tour

Enoteca di Fonterutoli, Via Giacomo Puccini, 4, 53011 Castellina in Chianti SI, Italy Marchesi Mazzei
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4.5 based on 2 reviews

The VIP Tour is dedicated to all wine lovers who prefer a private guide to visit our estate. You can customize the experience in Fonterutoli according to your interest, choose the arrival time, duration and wines to taste. The tour includes an introduction to the history of the Mazzei family, wine producers in the Chianti Classico since 1435 and continues with a visit to the cellar, showing the stages of the production process and the architectural aspects of a modern and avant-garde construction. Following is the exclusive tasting of our top wines or a vertical tasting of four special vintages of Castello Fonterutoli Chianti Classico Gran Selezione.

Inclusions: Alcoholic Beverages

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Reviewed By Steven M

Impressive facility and great tour with guide. He was extremely knowledgeable with the facility, wines and local sites. 25 Euro for the tour and tasting but consider it worth the price. This from a wine novice.

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