The 10 Best Wine Tours & Tastings in Gaiole in Chianti, Tuscany

May 4, 2022 Chanda Heide

Gaiole in Chianti is a comune (municipality) in the Province of Siena in the Italian region Tuscany, located about 40 kilometres (25 mi) southeast of Florence and about 15 kilometres (9 mi) northeast of Siena. Forbes named it number one in its list of "Europe's Most Idyllic Places To Live."
Restaurants in Gaiole in Chianti

1. Chianti Classico E-Bike Tour

Via delle Fonti, 1, 53019 Pianella SI, Italy Anima Toscana Bike Tour
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5.0 based on 3 reviews

The Brolio Classic bike tour will lead you to the Chianti area, one of the most important wine region in the world, for the quality of wine and beauty of landscapes. Chianti offers a unique landscape: gentle hills covered by vineyards and olive groves, small stone villages and farm houses. The start of the tour is at the border of Chianti. During the tour you will visit the Castle of Brolio with the 12th century castle gardens and the family’s private chapel. After this visit to the past, you will complete the bike tour with a wine tour and tasting in a Chianti winery. The tour includes also the lunch in local restaurant located at Castelnuovo Berardenga.

Inclusions: 1 Bottle of water per person, Wine tasting, Local bike guide, Private tour, Use of the electric bicycle, Use of helmet, Bottled water, Lunch in local restaurant located at Castelnuovo Berardenga, Ticket to the Castle of Brolio, Private transportation

Exclusions: Gratuities, Alcoholic beverages during the lunch

Reviewed By Antonio C

We got a great tour organized by Michele, he provided 2 excellent gravel bikes and a perfect itinerary tailored for our need. We had 3 great days cycling around the beautiful areas around Siena, Montalcino and Chianti.

2. 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.

3. Wine tasting in the historic Cantalici winery

Cantalici Winery - Soc. Agri. L'Antica Fornace Di Ridolfo S.S., Via della Croce, 17/19, 53013 Castagnoli SI, Italy Cantalici
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4.8 based on 4 reviews

The tasting at Cantalici is a way to immerse yourself in a family atmosphere to discover typical wines of the Chianti Classico production area, an experience that allows you to rediscover ancient flavors and the love for creating a product that contains the history of an entire family.

Inclusions: Tasting of 4.6 or 8 wines per person (depending on the option purchased), Tasting of Extra Virgin Olive Oil, Snack to accompany the tasting

Exclusions: Lunch

Reviewed By ErickHayes

The wine tasting was fun and tastes great if you like dry red wines. The som was very informative and my wife and I had a great time and bought 2 bottles. We also had a little buzz after the tasting. Great fast and attentive

4. Wine and Cooking Under the Tuscany Sun

ItalyBestExcursions

Enjoy this 5-day independent tour of Tuscany complete with a private driver. Starting from Rome, make your way to Siena where you will sleep all 4-nights. Over the course of your tour, see places such as: • Florence • Montepulciano • San Gimignano, • Pienza Upon your request, you may advise a professional tour guide to accompany you to several sites. Worry-Free and Safe Private Tour Experience, operated only with: - Expert Professional English-Speaking Drivers - Selected local Expert Licensed Tour Guides (when booked) - Welcoming comfortable and fully air-conditioned last model Mercedes or other similar private vehicles

Inclusions: 4 nights accommodation, Private tour, Hotel/Airport pickup and drop-off, Breakfast, Driver, Transport by air-conditioned minivan

Exclusions: Private guide (60EUR/hour), Additional touring time (20EUR/hour), Excess luggage charges (where applicable), Food and drinks, unless specified, Gratuities

Reviewed By Bernadette E

Just back since Sunday after 7 nights on ship - boarded in Barcelona 3rd Nov - cannot praise ship - staff - food and - organisation skills - fantastic. It was my 60 th birthday pressie and have to say it was SPECIAL. Hopefully will see you all again next year

5. Siena and Chianti Castle with Lunch&WineTasting from Florence

ItalyBestExcursions

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • Val D'Orcia countyside • Brolio Castle in Chianti area • Siena Wine Tasting and Lunch in the Brolio Castle included! Upgradable with licensed local guide in Private option. Pickup and dropoff will be at your accommodation. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

Inclusions: Hotel pickup and dropoff, Air-conditioned, fully insured and licensed legal vehicle with professional English Speaking Driver, Dedicated Local licensed Expert Tour Guide (upgradable in Private option), Brolio Castle in Chianti Area Wine Tasting, Brolio Castle Osteria Restaurant Lunch Included

Exclusions: Tipping is not included in our service fees, it is never mandatory although it is always appreciated

Reviewed By Bernadette E

Just back since Sunday after 7 nights on ship - boarded in Barcelona 3rd Nov - cannot praise ship - staff - food and - organisation skills - fantastic. It was my 60 th birthday pressie and have to say it was SPECIAL. Hopefully will see you all again next year

6. Livorno Port Shore Excursion: Siena and Chianti Castle with Lunch&WineTasting

ItalyBestExcursions

Enjoy this unforgettable High Level Shore Excursion and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • Val D'Orcia countyside • Brolio Castle in Chianti area • Siena Wine Tasting and Lunch in the Brolio Castle included! Upgradable with licensed local guide in Private option. Pickup and dropoff will be at your ship. Private or Shared Tour available options. Worry-free Shore Excursion: We will ensure your timely return to the Livorno Cruise Port for this activity. In the rare event your ship has departed, we will arrange for transportation to the next port-of-call. See our terms and conditions for full details.

Inclusions: Port pickup and dropoff, Air-conditioned, fully insured and licensed legal vehicle with professional English Speaking Driver, Dedicated Local licensed Expert Tour Guide (upgradable in Private option), Brolio Castle in Chianti Area Wine Tasting, Brolio Castle Osteria Restaurant Lunch Included

Exclusions: Tipping is not included in our service fees, it is never mandatory although it is always appreciated

Reviewed By Bernadette E

Just back since Sunday after 7 nights on ship - boarded in Barcelona 3rd Nov - cannot praise ship - staff - food and - organisation skills - fantastic. It was my 60 th birthday pressie and have to say it was SPECIAL. Hopefully will see you all again next year

7. Semi-Private Wine Tasting Tour: Sunset in Chianti

Simona S.r.l., Corso dei Tintori, 2, 50122 Firenze FI, Italy Italy Pass tours

Enjoy Tuscany at a more relaxed pace. Our afternoon tour by minivan will allow you to explore one of the world’s most beautiful landscapes: the Chianti region. Immerse yourself in stunning scenery characterized by vineyards, cypress trees, and golden hilltop villages. Explore Tuscany at sunset in a comfortable, air-conditioned vehicle Discover the beautiful landscapes and hilltop villages in a small group Visit a family estate and tour the cellars Enjoy tasting the local wines and traditional Italian appetizers

Inclusions: Comfortable air-conditioned car or 7-8 seater minivan, English-speaking driver, Visit to famous wine estate, Cellar tour, Wine tasting

Exclusions: Hotel pick-up, Tips

Reviewed By simom630

Interesting tour guided by Simona in German language, visiting all Renaissance rooms from giotto into albrecht duerer

8. Antinori Winery & Brolio Castle - Private Tour

City Florence Tours, Via dei Castellani, 18 rosso, 50122 Firenze FI, Italy City Florence Tours

You will leave with a private car from our office, here you will meet your driver with an exclusive car and your local guide as well as wine expert. The first stop of our visit to Chianti will be the Antinori estate in Bargino, a wonderful innovative winery, located in the green Chianti hills. Inside the cellar you can taste different types of wine, listening to stories and anecdotes about the Antinori family told by the guide who will accompany you on this wonderful journey. We will have lunch in the typical Tuscan restaurant "La Cantinetta di Rignana" halfway between the Antinori vineyard and the Brolio Castle. Here you can taste local salami, cheeses, Tuscan crostini, extra virgin olive oil, pasta or meat dishes, accompanied by wines and local products. The last stop of our view will be the Castle of Brolio and the Barone Ricasoli vineyard, here we will privately visit the castle and the vineyard, tasting different types of wine.

Inclusions: Lunch, Wine tasting, Licensed wine guide, Entrance to the Antinori Winery and Brolio Castle, Air-conditioned vehicle, Private driver with private transport

Exclusions: Visit to the underground cellars of Antinori, Snacks, Gratuities

Reviewed By Adventurer101573

We were visiting Florence for one week. City Florence Tours organized for us the tour of the importent places. And Marco and Giacomo did it with perfection. Marco is a very reliable and helpful organizer and Giacomo a highly knowlageable guide, who explains the many subjects with passion and is never dull.

9. Siena and Chianti Castle with Lunch&WineTasting from Florence

ILLYRIATOURS

Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • Val D'Orcia countyside • Brolio Castle in Chianti area • Siena Wine Tasting and Lunch in the Brolio Castle included! Upgradable with licensed local guide in Private option. Pickup and dropoff will be at your accommodation. Private or Shared Tour available options. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

Inclusions: Hotel pickup and dropoff, Dedicated Local Licensed Expert Tour Guide (upgradable in Private option), Brolio Castle in Chianti Area Wine Tasting, Brolio Castle Osteria Restaurant Lunch Included, Air-conditioned, fully insured and licensed legal vehicle with professional English-speaking Driver

Exclusions: Tipping is not included in our service fees, it is never mandatory although it is always appreciated

10. Tuscany Radda in Chianti Wine Tour and Tasting by Bike

Wine Bar La Cantina di Colle Bereto, Piazza IV Novembre, 5, 53017 Radda in Chianti SI, Italy Gusto Cycling

This give's you an opportunity to visit one of the best wine estates in the heart of the Chianti region with a rich history as well as enjoying a pleasurable and scenic cycle ride all day. The price includes hybrid bike rental for the day , however if you prefer you can have as a supplement an electric bike for the day . You will be accompanied by a cycle guide who will point out places of interest.

Inclusions: Cycle Guide for the day

Exclusions: Alcoholic Beverages

Reviewed By catfisher50

“I had the pleasure of visiting Toscana via Gusto Cycling even though I’m not an avid cyclist personally! Seriously, Gusto Cycling is much more than just getting on a bike… If you fancy a weekend get-away (or longer) to explore the wonderful sights & sounds of the Tuscan countryside and cities then make Gusto Cycling your ‘go too’ There is something for everyone: magnificent shopping, sightseeing, magnificent spas, an amazing array of food and wine, cultural trips. There are very few breaks where you can be sunning yourself on a beach one day, sightseeing in Florence the next & visiting an outdoor spa another, all whilst indulging in the more sumptuous food & wine the world has to offer. Cyclist or not, my husband and I cannot recommend Gusto Cycling enough…” Catherine Foster, Sept 2020 

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