The 11 Best Wine Country Day Trips in Florence

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

Review of a Tuscany day trip from Florence to Siena, San Gimignano, Pisa, and a Chianti winery lunch with practical tips.

“Pick up point is NOT where Viator send you. This tour is run by Walkabout Tours Florence...look for their sign at the Taxi Rank at the Station. Alex was a fabulous tour guide. Very good value for money. Alot of walking. Food fabulous for lunch.”

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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

Review of a full-day Tuscany tour from Florence to Siena, San Gimignano and Pisa, with winery lunch, wine pairing and practical tips.

“It’s bilingual English and Spanish. A very large group! The guides managed everyone very well. The lunch and wine tasting was a great experience!”

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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

Review of a full-day Tuscany tour from Florence to San Gimignano, Siena, Monteriggioni, and Chianti, with lunch and wine tasting.

“Visited lovely little villages and had free time to explore. Tour leader was friendly and helpful. Lunch was acceptable (appetiser was good, pasta main was average and no desert as promised, just a small biscuit). Wine was really nice but too expensive to buy. Overall worthwhile.”

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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

See Siena, San Gimignano, Monteriggioni, and taste Chianti wines on a full-day Tuscany tour from Florence.

“So we'll planned. No details are left to chance. They do such a good job of informing you of starting points, scheduling meetups etc. Our host Alex was wonderful and very knowledgeable. Seemed as though he was enjoying himself as much as we were. My family and I all agree that we will use Viator for all our tours on future Italian vacations.”

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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

Review of Florence’s Val d’Orcia day tour, with Montalcino, Pienza, Montepulciano, two wine tastings, prices, tips, and drawbacks.

“Everything they said on the description is on point!!!! Definitely enjoyed this tour! Sebastian and giovanni are great! 10 stars!!!!”

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

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

Review of a Florence day trip through Chianti with medieval villages, a Tuscan cooking class, lunch, wine tastings, and practical booking advice.

“Amazing tour! Lots of time in each place, and the tour guide Emma was so enthusiastic, knowledgeable and energetic that it was extra enjoyable!”

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7.Chianti Hills Half-Day Tour with Wine Tasting

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

Explore Chianti from Florence with vineyard walks, seven wine tastings, Tuscan snacks, olive oils, and a vinegar cellar visit.

“We had a great time with Chiara. We had our kids with us and she was super helpful and sweet.”

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8.Chianti Wine Tastings at Sunset Day Trip

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

Escape Florence for sunset Chianti wine tastings, family wineries, Tuscan scenery, local bites, and an optional countryside dinner.

“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

Review of a small-group Tuscany day trip from Florence to Siena, San Gimignano, and Chianti, with vineyard lunch, wine tasting, and private transport.

“We had a great time. Guide was great and informative. Perfect length of time for a day trip. Winery was great”

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

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

Taste Chianti wines, enjoy a Tuscan lunch, visit San Gimignano, and see Florence from Piazzale Michelangelo on this small-group day trip.

“The scenery was stunning. Wineries were so welcoming, wine was fabulous and food was so delicious. Our driver Daniel, made our tour most pleasurable. We had a wonderful tour day.. rainy day but was a stunning day!! Can’t wait to come back!! Totally recommend this tour !! Salute wine is excellent!!!”

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

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

Explore Volterra and San Gimignano from Florence with Tuscan lunch, winery tastings, local crafts, and championship gelato.

“We had a perfect day with Luciana. I highly recommend this tour or any other offered by Tuscany4Explore! We traveled with my 80 yr old father - Luciana answered all his questions and pointed out things of specific interest to him. We fell in love with Volterra - Luciana brought us to shops to sample local delicacies and showed us many special sites. She tailored the tour to history (our major interest). Her knowledge was superior. After Volterra, we had lunch. Our tour fell on a national holiday. Although many places were closed, Luciana found a special winery that treated us to wine, beautiful charcuterie and a pasta lunch! My…”

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