Wine Country Day Trips in Florence: the 11 We Rate

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 and cathedral visits, free time in San Gimignano and Pisa, and a family-run winery lunch with four wine tastings. Guides such as Alex, Sara, Davide, and Manolo are known for clear directions, humor, and good pacing. Choose the Pisa tower upgrade if you want to climb.

“I had a fantastic experience with this tour guide Sara and Milano from start to finish. Everything was well-organized, smooth, and thoughtfully planned, which made the entire tour stress-free and enjoyable. Sara was knowledgeable, engaging, and passionate, sharing interesting facts and stories that really brought the place to life. Sara also very friendly, patient, and happy to answer all my questions. The pacing was perfect, and I never felt rushed, while still getting to see and learn so much. Overall, it was a truly memorable experience, and I am so glad I chose this operator. Highly recommended for anyone looking for a professional, informative, and enjoyable tour!”

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2.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 with an English-speaking tour escort. Choose guided Siena access and a winery lunch with Tuscan wine, then enjoy free time in the medieval towns. Expect a full 12 hours, a group of up to 63, and plenty of walking.

“Great tour, saw so much and the scenery just breathtaking. The bus was comfortable and the stops one better than the next. Highly recommend the tour.”

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

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

Spend about 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, guided sights in Siena, and a winery lunch with three wines plus vin santo. Choose the Siena walking tour and cathedral option for added art and history. Guides may include Sandro, Marta, Alessandra, or Ilaria.

“Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.”

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

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

Travel by air-conditioned coach from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti estate. You’ll get guided time in Siena, free time in the hill towns, and a tasting of two or three wines with local snacks. Guides such as Alex, Jacopo, Gabrielle, and Constantino have earned strong praise for clear organization and good humor.

“Everything was organized perfectly. Jacob and Camilla were great and were very knowledgeable of the sites we saw. The wine tasting was awesome and we enjoyed all of the wine that was served. Would highly recommend to anyone visiting Florence to go on this day trip”

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5.Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines

★★★★★★★★★★4.5 · 1,106 reviews · 11 hours 30 minutes (approx.) · from $94

Spend about 11.5 hours touring Montalcino, Pienza, and Montepulciano from Florence. You’ll taste Brunello and Vino Nobile, sample pecorino, admire the Madonna di Vitaleta chapel, and pass the Gladiator filming area with guides such as Tabatha, Giovanni, or Sebastiano.

“The tour is long, and you spend a lot of time in a bus, but it is well worth it. The towns you visit are so amazing and the Val d’Orcia is beautiful. On top of that, we got to taste some good wine. My family enjoyed it:”

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6.Tuscany Day Trip: Chianti & Cooking Class Small Group

★★★★★★★★★★4.5 · 770 reviews · 11 hours 30 minutes (approx.) · from $167

Spend about 11.5 hours exploring Castellina, Monteriggioni, San Gimignano, and Certaldo from Florence. The day includes a hands-on Tuscan cooking class, lunch, dessert wine, two wine tastings, and free time in medieval towns. Guides such as Marco and Marta have earned special praise for their warm, helpful approach.

“This was a small group tour. I would recommend to purchase tickets for Siena sites ahead of time so that you save time and not stand in cues. The wine tasting and lunch at Poggio ai Laghi in Monterioggioni was so much fun and the views at San Gimignano were spectacular.”

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7.Chianti Hills Half-Day Tour with Wine Tasting

★★★★★★★★★★4.5 · 703 reviews · 5 hours · from $48Best value

Travel by air-conditioned Gran Turismo bus from Santa Maria Novella station to Chianti, where you walk among vines, visit a vinegar cellar, taste seven wines, vin santo, olive oils, cheeses, cold cuts, and seasonal Tuscan specialties. Guides such as Chiara, Emma, and Jordano have led recent departures, but staff can vary.

“We had a great experience. Thanks to our wonderful guide Chiara who told us important facts about the region and everything you need to know about Tuscan wine. She cared a lot about the wellbeing of the whole group for the trip and went above and beyond to make it perfect for everyone. Our driver Toto was also very skilled and we had a safe and relaxed bus journey. You can consider yourself lucky when you are making this tour with them!”

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8.Chianti Wine Tastings at Sunset Day Trip

★★★★★★★★★★4.7 · 274 reviews · 5 - 7 hours · from $151

Leave Florence in a comfortable air-conditioned car or minivan for two family-run Chianti estates. Tour the cellars, taste six wines with cheese, jam, and bruschetta, and stop for views near Greve, Montefioralle, and Passignano Abbey. Add a Tuscan dinner at sunset for the fullest experience.

“Our guide was knowledgeable, patient and communicative. We definitely recommend!”

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9.Ultimate Tuscany Day Trip with Wine & Lunch

★★★★★★★★★★4.8 · 221 reviews · 9 hours · from $229

Meet your English-speaking guide by the Carousel in Piazza della Repubblica, then travel by air-conditioned minivan to San Gimignano, a Chianti family winery, and Siena. Expect guided introductions, free time in both towns, a generous regional lunch with wine pairings, and a photo stop above Florence. Groups are limited to 14 people.

“The Ultimate Tuscany Day Trip was well worth doing. Our guide, Sandra, was very friendly and informative. We had plenty of time to explore Siena / San Gimignano, and the lunch at the winery was delicious. We had a great experience!”

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10.Wineries, Tastings, Lunch & San Gimignano Day Trip

★★★★★★★★★★5.0 · 82 reviews · 8 hours · from $223

Spend eight hours with a small group of up to eight, visiting two Chianti wineries, tasting wine and olive oil, eating a Tuscan lunch, and exploring San Gimignano. Guides such as Daniel, Christian, Lorenzo, and Guido are praised for making the day lively and easy to follow. Expect beautiful countryside, a famous gelato stop, and a full schedule.

“Lunch was not great considering the price paid for the trip. Would be better if able to visit a winery to see how wine is actually made rather than just 2 wine tasting sessions.”

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11.San Gimignano & Volterra Day Trip with Food & Wine

★★★★★★★★★★4.7 · 57 reviews · 9.5 hours · from $327

Travel from Florence into Tuscany with guide Luciana or another English-speaking guide, visiting Volterra, a winery, and San Gimignano. Expect guided walks, Etruscan and alabaster culture, a full Tuscan lunch, Vernaccia and Chianti tastings, and championship gelato. It is a long, active day with little free time.

“Luciana did an incredible job showing us a wonderful day. Her personal touches to make us comfortable - from ordering the most amazing lunch at a gorgeous restaurant in Volterra, to arranging a private wine tasting at the Il Pozzo vineyard - were at least as memorable as the sites in Volterra and San Gimignano. She managed to fit in everything from stops at an alabaster artisan to a cheese shop to an Etruscan history museum, and she also leapt into action when our daughter got carsick. I would recommend Tuscany4Explore for any Tuscan day trip!”

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