Italy · CHIANTI & TUSCAN COUNTRYSIDE TOURS

The 15 Best Chianti & Tuscan Countryside Tours

78 tours  ·  from $37 a head

Siena, San Gimignano and two cellars is the classic shape of this day, and most of them leave Florence before eight. These 15 differ on how many stops they cram in and how long you get at each, priced with the lunches marked.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Starting at Santa Maria Novella Station
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Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

1.Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

★★★★★★★★★★5.0 · 21,634 reviews · 11 to 12 hours (approx.) · from $114Our pick

Spend 11 to 12 hours touring Tuscany by air-conditioned coach, with guided Siena highlights, free time in San Gimignano and Pisa, and an optional farmhouse lunch with four wine tastings. Guides such as Sara, Davide, Alex, and Manolo are praised for keeping this busy day clear, friendly, and on schedule.

“Manolo and his team took great care of us and were so knowledgeable about all the places we went to. The sights were fabulous and the winery was absolutely exceptional! We had plenty of free time to explore, buy some souvenirs and make life long memories.”

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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch - Starting from Florence and settling into the coach
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Florence: Pisa, Siena and San Gimignano Day Trip with Lunch

2.Pisa, Siena and San Gimignano Day Trip with Lunch

★★★★★★★★★★4.6 · 9,771 reviews · 12 - 12.5 hours · from $58

Leave Florence for a full day of Tuscan sights: Siena’s medieval center, a Chianti winery lunch, San Gimignano’s towers, and Pisa’s Piazza dei Miracoli. Your multilingual tour leader handles the long-distance travel, while English is required for the Siena city and cathedral tours. Guides such as Val, Luca, and Leonardo have been praised for clear, friendly help.

“It was excellent. Fiama and Andre were very good. Very well planned. Guides were very helpful. They took care of all. Very clear instructions.Would recommend this tour to all visiting Florence .The itinerary was good. Covered all important places to visit.My family enjoyed the trip a lot. The guides also made the experience joyful”

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Florence: Pisa, Siena, San Gimignano, and Chianti Experience - Pisa and the Leaning Tower photo stop
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Florence: Pisa, Siena, San Gimignano, and Chianti Experience

3.Pisa, Siena, San Gimignano, and Chianti Experience

★★★★★★★★★★4.5 · 8,393 reviews · 12 hours · from $52

Spend 12 hours touring Tuscany from Florence, with stops at Pisa, San Gimignano, Siena, and a Chianti winery. Choose the lunch and wine tasting package, add a Siena walking tour, and reserve Leaning Tower tickets if you want to climb. Guides such as Barbara, Anna, and Lila are praised for clear local insight and good timekeeping.

“Emma our your guide went above and beyond. Our experience was great and so worth it! We took my grandpa who is 80 years old and he loved it! We saw so much stuff in just one day!”

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Florence: Chianti Wineries Tour with Wine Tasting - The first hour: Florence to the Chianti Hills
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Florence: Chianti Wineries Tour with Wine Tasting

4.Chianti Wineries Tour with Wine Tasting

★★★★★★★★★★4.5 · 8,301 reviews · from $56

Leave Florence by comfortable coach for two Chianti wineries. You’ll tour vineyards and cellars, taste three to four wines at each stop, and sample cheese, salami, bread, olive oil, and balsamic vinegar. Guides such as Martina, Cecilia, and Constantino have helped make this half-day outing lively, though group sizes can be large and food portions are light.

“Both wineries we visited were beautiful and the hosts were joyful and hospitable. Our guide shared interesting information about the wine region; she was cheerful and kind. The bus ride gave us scenic views of the area. What a great experience! We absolutely loved it. Our favorite thing, besides the great wine, was meeting guests on our tour from all over the world.”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - Siena begins with Piazza del Campo
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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

5.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Leave Florence at 7:30 a.m. for Siena, San Gimignano, and Pisa on a 12-hour coach tour. Depending on your option, you’ll get a guided Siena walk, Siena Cathedral time, and a winery lunch with wine pairing. Guides such as Constantino, Sara, and Jacopo are praised for keeping a large group on schedule, but expect plenty of walking and quick visits.

“Amazing day trip, with great guides sara & Gaia. Got to see pisa in daylight and night time. Food and wine lovey at the vineyard. Highly recommend”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Montepulciano, Tuscany’s wine town
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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

6.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 5,232 reviews · 12 hours (approx.) · from $83

Ride from central Rome to Montepulciano and Pienza with an English-speaking guide, then enjoy a three-course farm lunch with Tuscan wines, including Brunello di Montalcino. Guides such as Anna, Barbara, Antonino, and Flavio have been praised for lively history and practical tips. Expect a long day, steep streets, and limited free time.

“Antonino is a good and accomodating tour guide with Max as our excellent and courteous driver. A gentleman indeed. Helping us always. Highly recommended tour.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena: Gothic stone, yellow walls, and Piazza del Campo
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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

7.Siena, San Gimignano, Pisa & Lunch at Winery

★★★★★★★★★★4.8 · 4,538 reviews · 12 hours · from $112

Travel from Florence by comfortable coach to Siena, San Gimignano, Chianti, and Pisa. You’ll tour Siena with a local guide, visit the Gothic cathedral, enjoy an optional farmhouse lunch with four Tuscan wines, and finish at the Leaning Tower. Guides such as Sara, Alessandro, and Manolo are known for keeping the long day lively and well organized.

“It was convenient and comfortable. On time for drop and pick up. The guide was really good. Especially, a boat tour was good for us. Driving was safe. The driver was wonderful.”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Monteriggioni: a small fortress with a short visit
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

8.San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

★★★★★★★★★★4.5 · 4,432 reviews · 11 hours (approx.) · from $83

Spend 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, a three-course winery lunch, three Chianti wines, and Siena sightseeing. Select the Siena guide and cathedral upgrade for a fuller visit. Guides such as Sandro, Marta, Ricardo, and Ilaria are praised for clear, friendly service.

“Sandro and Fabi were fantastic, well organised and very informative. Great meal and wine tasting too! Even the rain couldn't dampen the mood.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Pisa’s Field of Miracles in 80 minutes
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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

9.Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

★★★★★★★★★★4.6 · 4,354 reviews · 12 hours · from $77

Travel from Florence through Tuscany to Pisa, San Gimignano, Chianti, and Siena on a 12-hour guided coach tour. You will see Pisa’s Field of Miracles, medieval towers in San Gimignano, and Siena’s Piazza del Campo. Choose the lunch and wine pairing, plus Siena Cathedral and guided walking tour options. English and Spanish tours are available.

“This tour is worth every penny, it’s an entire day of visiting beautiful places and making memories. Our guide Sandro is very knowledgeable and friendly”

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Chianti Wine Tour from Florence - Riding the Via Chiantigiana into the hills
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Chianti Wine Tour from Florence

10.Chianti Wine Tour from Florence

★★★★★★★★★★4.5 · 3,979 reviews · 5 hours (approx.) · from $59

Leave Florence by air-conditioned coach for two Chianti wineries along the Via Chiantigiana. You’ll taste six or seven Tuscan wines, sample cheese, salami, bruschetta, olive oil, and balsamic vinegar, and tour vineyards and cellars with local hosts. Guides such as Aaron, Cristina, Alessandra, and Maria Luisa have helped make this five-hour outing especially engaging.

“Both wineries were amazing! Lots of Knowledge about making the wine and very personal wanted you to ask questions and just talked to you during the tour. Tommas from the second location super friendly and did an excellent job! Both shipped to the US and you could buy another glass while you walked around the site. Both had some snacks at the venues, but would eat lunch or dinner before going.”

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From Florence: Small Group Wine Tasting Tour to Tuscany - The first estate, cellar traditions and three wines
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From Florence: Small Group Wine Tasting Tour to Tuscany

11.Small Group Wine Tasting Tour to Tuscany

★★★★★★★★★★4.9 · 3,902 reviews · 4.5 hours · from $105

Leave Florence by air-conditioned minibus for two Chianti Classico wineries. Taste about six wines and local olive oils with cheese, salami, cold cuts, and bruschetta. English-speaking guides such as Jason, Leo, Jonathan, and Raffaele have helped make this a lively, social outing, though the wineries and guide can vary.

“This tour was incredible from start to finish! The scenery was breathtaking. The wine tasting was fantastic, with a great selection of local wines that were both delicious and unique. Our guide was friendly, knowledgeable, and made the whole experience even more enjoyable with interesting stories and insights about the region. Everything was perfectly organized and relaxed. We couldn’t have asked for a better day — highly recommend this tour to anyone visiting Tuscany! 🍷🌻🇮🇹”

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From Florence: San Gimignano, Siena, and Chianti Wine Tour - Siena and the 85-minute introduction
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From Florence: San Gimignano, Siena, and Chianti Wine Tour

12.San Gimignano, Siena, and Chianti Wine Tour

★★★★★★★★★★4.5 · 3,762 reviews · from $164

Travel from Florence to Siena, a Chianti winery, and San Gimignano in about nine hours. Expect an air-conditioned minibus or coach, multilingual guidance, five wine tastings, Tuscan specialties, and free time in both medieval towns. Guides such as Marco, Lyla, Marta, and Enrieta are praised for keeping the day clear, friendly, and on schedule.

“The experience couldn’t get any better. Marco is an excellent guide and a person! Highly recommended. I went by myself, but made very good friends along the way 💫 Italy is mesmerizing and do not hesitate to take this tour 🥰🌟 p.s. I would recommend to get lunch at the winery. Grazie”

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Florence: Siena, San Gimignano & Monteriggioni with Tasting - Meeting the coach near Santa Maria Novella
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Florence: Siena, San Gimignano & Monteriggioni with Tasting

13.Siena, San Gimignano & Monteriggioni with Tasting

★★★★★★★★★★4.6 · 3,218 reviews · 11 hours · from $46Best value

Spend 11 hours exploring Tuscany by air-conditioned coach, with stops in Siena, San Gimignano, and Monteriggioni plus three Chianti wines and local snacks. A multilingual guide, Siena walking tour option, and free time in each town keep the day organized. Expect a full schedule, cobblestones, and a large group.

“Nice day trip from Florence to Siena, San Gimignano and Monteriggioni. The bus was comfortable and the guide was knowledgeable of the areas. The weather was foggy so it made for some nice pictures. I recommend this tour seeing these beautiful cites and culture in Italy.”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Starting at Piazzale Montelungo in Florence
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

14.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Spend about 10.5 hours touring Tuscany from Florence, with stops in Monteriggioni, Siena, San Gimignano, and the Chianti hills. You’ll see Piazza del Campo and Siena Cathedral, enjoy free time in medieval towns, and taste two or three Chianti wines with regional snacks. English and Spanish are regularly offered.

“Ronaldo and Roberto did a great job of getting us to our destinations and communicating things to do at each stop. This tour is a large group tour on a coach bus. We still kept to our schedule. Siena is beautiful along with the other stops. The only thing i wish were different was the order of the stops. It was close to dark when we arrived to San Gimignano and would have preferred to be in Siena in the evening. Thanks for conducting the tour, so we could see more on our Italy trip!”

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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch - San Gimignano: two hours among the towers
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Florence: S. Gimignano, Siena, Chianti & Wine Tasting Lunch

15.S. Gimignano, Siena, Chianti & Wine Tasting Lunch

★★★★★★★★★★4.6 · 2,427 reviews · from $89

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. You get free time in San Gimignano, a three-course lunch with three wines, and an optional guided Siena Cathedral visit. English and Spanish tours are available, with guides such as Marta, Aaron, Ricardo, and Sara leading some departures.

“Our tour guide Aaron was the best! Can’t really ask more.”

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