A medieval city rich in history, known for its stunning Piazza del Campo and the magnificent Siena Cathedral.
Don't miss: Climbing the Torre del Mangia for panoramic views of the city and countryside.
Chianti is just an hour away from Florence. Whether you take a tour bus or drive yourself, the journey itself is an experience with beautiful views of vineyards, olive groves, and medieval villages.
Often called the "Gateway to Chianti", this lively town is known for its triangular main square, Piazza Matteotti, lined with porticos, shops, and restaurants. Do visit the Antica Macelleria Falorni, a butcher shop known for its high-quality meats and the famous Viticcio Winery.
Chianti's peak tourist season is from June to August, attracting crowds for its great weather and wine festivals, especially in towns like Greve and San Gimignano. For a more relaxed visit, consider the shoulder seasons of spring (March to May) or fall (September to November), when the crowds thin, and the landscapes shine.
For a vibrant vineyard experience, visit during the grape harvest season from September to October, when you might even join in the harvest.
For the best weather, visit Chianti between April-June or September-October, when temperatures range from 15°C to 25°C (59°F to 77°F). These months provide comfortable conditions for exploring vineyards and towns, with spring blooms or autumn colors adding to the scenic beauty. Summer can be hot, with temperatures over 30°C (86°F), making outdoor activities less comfortable.
The distance between Florence and the Chianti region is approximately 35 kilometers (21 miles) by road. It's a 45 minutes - 1 hour drive.
The best way to reach Chianti from Florence depends on your preferences. While buses and trains are budget-friendly, they require changing stops and aren't that flexible. Renting a car gives you freedom to explore but can be tricky with rural roads. Tours are the most convenient option, offering round-trip transfers, vineyard visits, and meals, letting you relax while everything is taken care of.
It's recommended to book your Chianti tour at least two weeks in advance during peak season (June to August) to ensure availability, especially for popular tours that include wine tastings and visits to multiple towns. During other seasons, booking 3 days to one week in advance is fine.
While the core itinerary is standardized to ensure you experience the best of Chianti, we offer a variety of permutations and combinations to suit your preferences. You can choose from top experiences like visiting specific wineries, exploring historic towns such as Siena and San Gimignano, or even adding a traditional Tuscan lunch. This flexibility allows you to tailor your day while still benefiting from a well-planned tour.
The Chianti region is known for its laid-back, family-oriented culture, making it a comfortable environment for families to enjoy wine tasting and local cuisine together. Although, do note that guests under 18 must be accompanied by an adult to book our tours. Many wineries in Chianti are family-friendly, offering activities like scavenger hunts, outdoor play areas, and educational components about winemaking. It is generally recommended that children be at least 5 years old to enjoy the experience.
Most Chianti tours are conducted in English, and guides are usually multilingual. However, knowing a few basic Italian phrases can enhance your experience, especially in smaller towns and local markets.
When attending a wine tasting, it's essential to follow some basic etiquette to enhance your experience and show respect for the hosts. Avoid wearing strong fragrances that can overpower the wine's aromas. Hold your glass by the stem to avoid warming the wine and leaving fingerprints. Take your time to savor each sip, and feel free to use a spittoon if you're tasting multiple wines. Engage with the pourer to learn more about the wines, and cleanse your palate between tastings. It's also perfectly fine to spit out wine to keep your palate fresh and avoid intoxication. Dress smart-casual, wear comfortable shoes, and keep an open mind to discover new flavors.
We had an amazing time! Our host (Amari?) did a great job explaining some of the history of the city as we travelled through Florence and into Tuscany. The driver did a great job getting us there safely and in great time. The vineyards were both top notch with friendly staff, beautiful vineyards and delicious wines. Would definitely book another excursion and even this same one again! Thank you.
Hassle free experience with Headout, Ciao Florence tour to Chianti wineries was great and definitely value for money. Clean airconditioned bus, English speaking guide and no pressure wine tasting!
Great host, informative and delicious!
Martina was an engaging hostess. It was a well run tour and ticked all our expectations
The tour guide and bus driver were so patient and nice as they waited for us to get on the bus since we were late due to transportation issues.
Despite choosing the Spanish tour, the group was mixed in English, Spanish and Italian. However, the guide who accompanied the group gave explanations in all three languages. Only in the 2 wineries we visited was the language only in English or Italian. The 2 visits to the wineries were good, with a small tasting of bread with olive oil and 3 wines in each (starter wines).
Butique winery visit was indeed great!
Comfortable and pleasant presentation both vinyards
The classic Tuscan experience – two scenic estate visits with regional pairings and local bites.
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We absolutely loved the locations! It was easy to get our tickets, they had a good mix of free time, wine tasting and lunch and the option of a walking and cathedral tour in Siena. The tour guide did a really good job of managing a large group but it was a mission to get such a large group all back at the same time which was frustrating. Nice tour but if you don't like large groups, rather visit the locations on your own.
The guide was excellent. She was very informative and clear in her instruction. The bus driver was a safe driver. However, the amount of time allotted per location was insufficient. It was always a rush to get to see everything...with the exception of Pisa. Between San Gimignano and Siena, the air conditioning stopped working. Would the maintenance on the buses not be done before the beginning of the summer and busy tourist season? Needless to say, the ride was very uncomfortable. I will not be recommending this company to any of my friends.
The complete package, very well organised and a brilliant tour guide can't remember her named but she was the English tour guide.
Great guide, everything according to plan, punctuality and great cities
See Pisa, San Gimignano & Siena in a single day—iconic sights, Tuscan charm, and a hearty lunch.
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Supervisors Martha and Julio provided perfect guidance. Clear in information and always approachable. TOP With a wine company, we expected a winery in the countryside. This was a factory site. So ambience was a bit less, despite the enthusiastic employee of the winery. Nice and enthusiastic. Despite the severe thunderstorm in Siena we had a nice day.
We loved the three beautiful cities we visited, including the crown of Tuscany which wasn't on the itinerary. Paying to walk on the city walls was interesting and views were good, but we were on metal bridges, not the actual walls. There are two different access points so be sure to try both. Lunch was at a restaurant with a very small vineyard where we could walk and take photos. The tastings were all good but primarily a sales pitch. The pasta lunch was just ok. If you take the cathedral tour in Siena (recommended but additional cost) make sure you know how to get back to the meeting point!
A lot of history in each of the towns, beautiful scenery, and comfortable rides.
Everything was neat, the guide explained excellent everything we saw on the tour, the times in the places were perfect and the wine tasting and food was perfect, we would do the tour again.
The visit to Siena, San Gimignano & the Chianti lunch & wine tasting were all very good. The tour leader was excellent.
The guide was excellent and the tour ran to time in all locations. Everything was as expected or better.
Fabulous guide, Sandro and driver, Fernando! The winery was also a big highlight. So much fun.
Three Tuscan treasures, one unforgettable day—Siena, San Gimignano & Chianti with lunch.
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Well planned,all on time ! Amazing guide Cecilia
Explore Siena’s medieval charm and indulge in the flavors of Chianti on a laid-back Tuscan escape.
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Fantastic vineyards and winery. Well organised. The "lunch", while delicious, was disappointing as it was hardly more than a snack
Educational, personal and relaxing. Ticketing with Headout was ok.
Deep dive into Chianti’s rich food and flavor traditions with gourmet pairings and estate visits.
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Florence pick up
Small-group day trip around Chianti
Round-trip Mercedes minibus or minivan transfers
Guided tour of 1 olive oil mill & 3 wineries with tastings
Typical Tuscan lunch
Guided tour of a Tuscan village
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Very disappointed in the tour. Our guide greeted us by saying that English was not her best language but she was sure everything would be okay. The bus driver drove aggressively to the wineries, impatient with the traffic, sounding his horn and flashing at all on the road. Wineries were nice but no olive oil tasting as advertised and very little food. Not value for money. Most importantly though our guide left two of the party behind at the first winery as the bus driver refused to wait for them. Confusion around the time we had to be back on the bus because our guide did not translate properly meant we left two people behind. Driver and guide argued all the way to the second winery. Finished the second tour. No bus to greet us. Had to go back for the two people he had left behind. We're arrived back in Florence which was dark and cold 1:5 hours late. 6:5 hours away with no food. Left in the bus depot cold, tired and hungry. Not a good experience at all. Tuscany countryside is magnificent which is why I've given 2 stars.
The wine tasting was very short
Bus driver got lost and we had our wine tour cut short because of that.
Discover Chianti’s historic estates on a guided tasting tour through Tuscany’s countryside — roundtrip transport from Florence included.
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This ticket has the following options that you can choose from:
Savor the flavors of Chianti with scenic tastings across two Tuscan countryside estates
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You can cancel these tickets up to 48 hours before the experience begins and get a full refund.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
You can cancel these tickets up to 24 hours before the experience begins and get a full refund.
