What to do and see in Radda in Chianti, Tuscany: The Best Wine Tours & Tastings

January 14, 2022 Jacquiline Delozier

Radda in Chianti is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 35 kilometres (22 miles) southeast of Florence and about 15 km (9 miles) north of Siena.
Restaurants in Radda 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. Self-Drive Vintage Vespa Tour at Sunset Wine Tasting

Via Gherardo Silvani, 149, 50125 Firenze FI, Italy 500 Touring Club
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5.0 based on 9 reviews

Combine the romance of a Tuscan sunset with the thrill of driving a Vespa scooter with this 3.5-hour self-drive sunset Vespa tour from Florence. Ride through the Tuscan hills and experience the simple joy of the Italian lifestyle .After some photo ops partake in a wine tasting experience, sampling of local cheeses and cured meats.

Inclusions: Introduction to the beautiful Vespa scooter, Driving through Tuscan and Chianti countryside, Lovely country views over Olive groves and Chianti Classico vineyards, Full Tour Commentary from an experienced guide, Note: We will have 2 people from same party on 1 Vespa.

Exclusions: Gratuities

Reviewed By forrest2207

Sadly due to recent times it was just the two of us on this tour, however did we get lucky! Our tour guide Marti ensured that we felt confident driving our little green beauty before we set off in to the Tuscan hills. Marti is an absolute credit to this tour, with her vast knowledge of the region and her experience as a sommelier. The tour is not only fun but informative as well. It gets you out of the city, you see the beautiful countryside with plenty of pit stops for photo opportunities and then end up in a stunning location for a light lunch and wine tasting down in the cellar. If you do one day trip whilst in Florence THIS IS THE ONE!

3. Self-Drive Vintage Vespa Tour with Wine Tasting from Florence

Via Gherardo Silvani, 149, 50125 Firenze FI, Italy 500 Touring Club
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5.0 based on 15 reviews

You have dreamed of a romantic Italian getaway. Be ready to make that dream a reality with this 4.5-hour Vespa scooter tour from Florence with a wine tasting experience. Your guide will lead the convoy on the adventure of a lifetime as you drive your own scooter through the countryside. The breathtaking view of the Tuscan hills, the historic Tuscan Villas, cypress lined roads, endless vineyards and captivating olive groves are visuals you will never forget.

Inclusions: Introduction and safety briefing of the Vespa scooter, Several photo-op stops with views over olive groves and Chianti Classico vineyards, Professional wine tasting in enchanting setting, Take in the historic cultural feel of the Villa, Note: We will have 2 people from same party on 1 Vespa.

Exclusions: Gratuities

Reviewed By forrest2207

Sadly due to recent times it was just the two of us on this tour, however did we get lucky! Our tour guide Marti ensured that we felt confident driving our little green beauty before we set off in to the Tuscan hills. Marti is an absolute credit to this tour, with her vast knowledge of the region and her experience as a sommelier. The tour is not only fun but informative as well. It gets you out of the city, you see the beautiful countryside with plenty of pit stops for photo opportunities and then end up in a stunning location for a light lunch and wine tasting down in the cellar. If you do one day trip whilst in Florence THIS IS THE ONE!

4. Self-Drive Vintage Vespa Tour with Tuscan Gourmet Lunch

Via Gherardo Silvani, 149, 50125 Firenze FI, Italy 500 Touring Club
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5.0 based on 1 reviews

Get into the Tuscan countryside with this fun 5.5-hour self-drive vintage Vespa tour from Florence, including a picnic lunch and wine tasting. This exclusive opportunity is perfect for anyone wanting to escape the congestion and crowds of the city. Enjoy the crisp and fresh air as you tour the soft rolling Tuscan hills on Vespas. The Renaissance painters chose these landscapes for a reason, and you will wholeheartedly agree.

Inclusions: Introduction to the beautiful Vespa scooter, Driving through Tuscan and Chianti countryside, Lovely country views over Olive groves and Chianti Classico vineyards, Full Tour Commentary from an experienced guide, Full Tuscan lunch, Wine tasting experience, Note: We will have 2 people from same party on 1 Vespa.

Exclusions: Gratuities

Reviewed By forrest2207

Sadly due to recent times it was just the two of us on this tour, however did we get lucky! Our tour guide Marti ensured that we felt confident driving our little green beauty before we set off in to the Tuscan hills. Marti is an absolute credit to this tour, with her vast knowledge of the region and her experience as a sommelier. The tour is not only fun but informative as well. It gets you out of the city, you see the beautiful countryside with plenty of pit stops for photo opportunities and then end up in a stunning location for a light lunch and wine tasting down in the cellar. If you do one day trip whilst in Florence THIS IS THE ONE!

5. WINE TOURS VIP Antinori and Ceramic of Chianti Classico

GT Gianluca Tours
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5.0 based on 1 reviews

A wonderfull day with few stops for panoramic photos of the beautifull countryside of Chianti, guided from an English speacking professional driver with a confortable Mercedes E class, the lunch and wine tasting it will be on original Chianti winery on the heart of Chianti Classico where the costumer can eat the typical food from our land and taste our spetacular wines. The pick up and the drop off will be by the Hotel or anywhere the client want in Florence city.

Inclusions: Private transportation, WiFi on board, Bottled water

Exclusions: Lunch, Alcoholic Beverages, Cellar tours in Antinori

Reviewed By Netvigation

Excellent service. Our driver Leonardo was wonderful and went out of his way to accommodate our requests. He enhanced an already memorable evening.

6. Full day wine tour from Florence: Chianti and Badia a Passignano

Via Elio Gabbuggiani, 7, 50144 Firenze FI, Italy My Tour in Italy
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5.0 based on 5 reviews

Spend your day in the Countryside surrounded by Chianti hills and enjoy the view that only this place can offer while tasting and drinking incredible wines and local products. Forget the touristy places and live this authentic experience; your visit to Tuscany would not be complete if you did not experience a traditional wine tasting and meal in the great Chianti area.

Inclusions: Travel by GT coach or minivan, Expert tour guide, 2 wine tastings in 2 Chianti wineries, Typical Tuscan lunch with barbecued meat and vegetables, Visit Badia a Passignano

Exclusions: Gratuities, Pickup and dropoff

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.

7. Small group Chianti Classico Wine-Food Tour from Montevarchi.Boutique wineries.

Sottopasso F.S., 52025 Montevarchi, Province of Arezzo, Italy Viaggi d'Ambra
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5.0 based on 14 reviews

Away from tourist routes, from Montevarchi train station we will drive you in one of our comfortable vehicles to a quintessentially Tuscan area (it's easy to reach this train station from Florence, 35 minutes ride, and Arezzo, 25 minutes ride). We will visit medieval towns and some of the best-known boutique wineries. Those producers make up for their small production numbers by crafting superb quality wines with great passion. During the visit through the vineyards you can see where and how Sangiovese grapes grow. You will be revealed pearls of country wisdom, you will be told about the difficulties of working the land, and share stories of what it is like to produce a wine that graces tables around the world. This tour is special because it allows you to discover smaller, niche producers. Lunch at a winery or in a small osteria is a must – Chianti wines are meant to be enjoyed with the delicious dishes of Tuscan cuisine. Wine and food will delight both your palate and heart!

Inclusions: Visit of two wineries with at least 3 glasses of wine each place and extra virgin olive oil tasting., The professional english speaking driver will explain you the attractions, the wine traditions, Lunch, Air-conditioned vehicle

Exclusions: Professional licensed guide, Gratuities

Reviewed By flobo5

My family and I first came into contact with Viaggi d'Ambra in July when I contacted them about a Chianti tour (see previous review) - we loved it so much, we didn't only book once again, but twice! My husband and I had the pleasure of a tour with Azzurra in the Montepulciano and Montalico regions in August - it was amazing! Both wineries were in lovely positions and the hosts were delightful. We also had time to explore the beautiful town of Pienza - not to be missed! After two fabulous tours, we booked to return to Tuscany in October. This time Christian took us on an amazing tour of northern Chianti. We visited the beautiful town of Greve and two fabulous wineries. Without Christian, we would never have found them and their wonderful wines! This year has all been a bit mad, but do book early for tours next year as Azzurra and Christian are fantastic people and know the area like no other. If you don't book, I can see myself taking tours with them daily - it really is such a fantastic experience and such a varied area! Grazie mille both of you!!!

8. Small-Group Chianti Wine-Tasting and Castles Trip from Siena

Piazza San Domenico, Piazza S. Domenico, 53100 Siena SI, Italy Tuscan Escapes
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4.9 based on 35 reviews

Combine Chianti's fine wines with its impressive castles on a full-day trip from Siena! Giving the rugged Tuscan landscape a remarkable grandeur, these stunning Italian castles are a must-see for any visitor to the region. With your expert guide, visit Castello di Brolio, renowned as the birthplace of Chianti wine. Sample the esteemed Chianti Classico wine, enjoy an authentic Italian lunch at a Tuscan wine estate and tour the cellars to learn about the passion behind this traditional wine directly from the producer. Enjoy some of the region’s best wines directly at the winery. Numbers are limited to eight people on your small-group trip, ensuring you'll receive personalized attention from your guide.

Inclusions: Professional guide, Lunch, Wine tasting, Air-conditioned vehicle

Exclusions: Gratuities, Hotel pickup and drop-off, Entrance to Castello di Brolio

Reviewed By Pioggiola

We did a 3-hour private tour of Siena with Giorgia this summer with our two teenage children. It was just perfect! Giorgia is extremely knowledgeable about all aspects of Siena and beyond, and it clearly showed in the depth of her answers to the very many questions that we asked. She was flexible to adapt the tour based on what we were interested in. Although not originally from Siena, she knows and loves the city like a local and has the ability to make the tour unforgettable. 160 Euros for a fantastic private our of Sienna. Very good value for money. Probably the best private city tour that we have ever done.

9. Tour and Tasting at an Organic Winery in the Heart of Chianti Classico Area

Fattoria di Montemaggio, Località Montemaggio, 53017 Radda in Chianti SI, Italy Fattoria di Montemaggio
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4.9 based on 29 reviews

Visit an organic estate that organizes guided tour and tastings in the heart of Chianti Classico area, between Radda and Panzano in Chianti. During the tour it is possible to see the vineyards and the wineries, hear a guided explanation of the wine-making process in order to make wines of the highest quality. The visit is then followed by the tasting of the 3 or 6 wines, accompanied by small but tasty snacks, including bread with olive oil of own production and Grappa.

Inclusions: Beverages, Light refreshments, Snacks, Wine tasting, Tour

Exclusions: Hotel pickup and drop-off

Reviewed By liubapaladi93

It was an amazing experience with a wonderful staff. All the people was friendly and at the end they recommended us a pleasant place for lunch. The wine tour was very informative and with a lot of wine degustation, we tasted everything and it was very delicious.

10. Siena Vespa Tour Including Lunch at a Chianti Winery

Piazza Gramsci, 53100 Siena, Province of Siena, Italy My Tour in Italy
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4.8 based on 52 reviews

Explore the Tuscan hills by Vespa scooter on a day trip from Siena, and visit a Chianti winery for lunch, too! After a practice session, choose to drive your own scooter or hop on behind a tour escort -- (depends on the option selected). Under the watchful eyes of a guide and tour escorts, ride in a convoy, heading to a Chianti winery in the lush Tuscan countryside. Tour the vineyards and cellars, sit down for a wine-tasting session, and then relax over an ‘antipasto’ lunch before returning to Siena.

Inclusions: Hotel pickup and drop-off (for Hotels located within 20 km from the center of Siena), Professional tour escorts and guide, Use of helmet, Winery tour with Wine tasting, Lunch made with typical fresh dishes

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.

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