The 10 Best Wine Tours & Tastings in Castellina In Chianti, Tuscany

December 29, 2021 Jacquiline Darosa

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. Brunello Wine Tasting from San Gimignano

Porta San Giovanni, Via S. Giovanni, 126, 53037 San Gimignano SI, Italy My Tour in Italy
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5.0 based on 1 reviews

Enjoy a day spent in the beauty and harmony of the Tuscan countryside. Visit the surrounding areas of Siena . Explore the region of Val D'Orcia and its secular wine-producing tradition, together with the stunning Montalcino fortress. Wine tastings included.

Inclusions: Wine tasting, All taxes, fees and handling charges, Expert multilingual escorts, Hotel pickup and drop-off, Transport by air-conditioned minivan for a maximum of 8 people

Exclusions: Gratuities, Lunch

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. 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. 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.

4. 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 ????

5. 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!

6. 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.

7. 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!

8. Truffle Hunting with Wine Tasting in Tuscan farmhouse

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 2 reviews

An amazing daytrip in the countryside to enjoy the gems of Chianti area production: truffle, wine and extra virgin olive oil, all in and around the same traditional family farm. Follow the expert truffle man and his trained dog in the forest to witness with your eyes how it is possible to find underground these edible treasures and the strong bond between trees and truffles. Back in the farm, you will have a wonderful lunch based on the truffle you found in the woods. Extra virgin olive oil and traditional Chianti Classico wine will accompany your lunch with a guide that will explain all the procedure of oil and wine production, showing all the phases of the work. Spend a day in a hidden place in the Tuscan country away from the city, with both the emotion of the hunting and the relax of the home-made lunch you will enjoy surrounded by the sounds of nature. For sure a memory will last forever.

Inclusions: Transport by air-conditioned minivan, Tour escort and Driver/guide, All activities, 3-course lunch, Wine tasting, Extra virgin olive oil tasting, Honey tasting, Alcoholic Beverages

Exclusions: Gratuities

Reviewed By SRif914

We took a private tour of two incredible vineyards in Montalcino while on our honeymoon. Gaia was our tour guide and was absolutely incredible! Her knowledge of the wine industry and outgoing personality made this one of the best experiences of the trip. We will absolutely be recommending this tour to our friends and are excited to come back and explore more of Tuscany with Tuscany Private Tours.

9. 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..

10. PRIVATE Full-Day Siena and Chianti Classico Wine Experience.

UniqueTuscany private Tours
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5.0 based on 6 reviews

• EXPERIENCE FOR YOUR PRIVATE GROUP • Leave behind the bustling city of Florence with a private full-day tour in a luxury Mercedes Minivan. Stroll through the Gothic streets of Siena and discover the black-and-white art and architecture of its historic center, a UNESCO heritage site. Taste renowned Chianti wines and authentic Tuscan cuisine in famous family-owned cellars of local olive oil and aged balsamic vinegar. • 8hr Full-Day private tour of Siena and Chianti from Florence • Pick-up and drop off at your selected hotel/ location (Florence Down Town) • Private transportation by Mercedes Minivan, Air-Conditioned • Tasting of cold cuts and cheeses from the exceptional Falorni butcher shop • English-speaking licensed driver • Learn about local history, food and culture • On request we can organize Lunch in Farm or Winery. (highly recommended)

Inclusions: Pick-up and drop-off at your selected hotel/location (in Downtown Florence), Private transportation by Mercedes Minivan air-conditioned , Unlimited cold mineral water , Tasting of cold cuts and cheeses from Falorni butcher, Local guide tour in winery, On-Board WiFi

Exclusions: Lunch and wine tasting on farm or winery (to be paid on-location from 25€pp to 45€pp), Wine tasting (to be paid on-location from 0€pp to 25€pp), Private city guide.

Reviewed By Journey40774728396

We booked with Alessandro for a day trip from Florence to Siena and San gimignano as we were in Italy for my wife's business, so we decided to visit Tuscany for the third time. COVID wasn't a big deal yet, but the cities were practically deserted.. Alessandro was a delightful tour guide and host. (great with communications, reasonable price and very comfortable car and driver) Alessandro is extremely friendly, and it was a pleasure to meet him and have accompanied him around for the day. I don't know how he did it but every time we were leaving from anywhere, without even having to text him or look for him, he was there waiting for us with the door open! We were able to spend a really relaxing and enjoyable day touring the vineyards thanks to Alessandro so organized and professional! We love Florence!!!

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