14 Wine Country Day Trips in Italy Worth the Detour

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.Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

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

Review of Rome’s Tuscany and Montepulciano day trip, with a Tuscan farm lunch, wine tasting, Pienza, transport, costs, and practical tips.

“Great experience! Starts early, so most breakfast places are closed... except McDonald's!! which was nearby, btw (done by design?) The tour was well organized. We got to see and do a lot on our day-trip to Tuscany.”

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4.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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5.Tuscany & Montepulciano Day Trip with Lunch & Wines

★★★★★★★★★★4.7 · 3,004 reviews · 11 - 12 hours · from $81

See Montepulciano and Pienza from Rome with a vineyard lunch, Brunello wine tasting, expert guides, and Tuscan countryside views.

“Antinanio and the crazy bus driver were fantastic!! Thank you”

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6.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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7.Amalfi Coast Day Tour from Sorrento with Light Lunch and Wine

★★★★★★★★★★4.5 · 1,148 reviews · 8 hours 45 minutes (approx.) · from $139

Review of the Amalfi Coast day tour from Sorrento, with Positano, Amalfi, Ravello, lunch, wine, scenic stops, and a small group.

“Our gudie was a safe driver and pointed out sights along the way. She made sure to pull over at areas of interest. Our lunch was very good with a beautiful view.”

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8.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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9.Bagnoregio & Orvieto Day Trip with Wines & Lunch

★★★★★★★★★★4.6 · 1,075 reviews · 12 hours · from $93

Review of a 12-hour Rome day trip to Civita di Bagnoregio, Orvieto, and a Tuscan winery with lunch and five wines.

“The tour guide, Kiara, is so professional and knowledgeable. She told us so much history about Rome and the three regions we visited, and shared many interesting facts about these places. Her time management is also accurate, so we are fully on schedule.”

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10.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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11.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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12.Guided Etna Wine Tasting Half-Day Tour

★★★★★★★★★★4.7 · 444 reviews · 5 hours · from $68

Review of Taormina’s Etna wine tour, with Gambino winery, four tastings, Sicilian appetizers, village scenery, transport, and practical tips.

“The tour was informative. A beautiful part of Sicily. We tried 4 different types of wine. 2 Etna and 2 from their winery in another part of Sicily. They were generous with the wine tasting. The food pairing of cheese and antipasti was also good. Really good value for money and would definitely recommend- a must do excursion.”

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13.Full-Day Etna, Wine & Alcantara Canyons Tour

★★★★★★★★★★4.9 · 390 reviews · from $116

Review of a full-day Etna tour from Taormina with crater hikes, a lava cave, Sicilian lunch, wine tasting, and Alcantara Canyon views.

“Our tour was really very well organized. All the equipment we needed were prepared for us, and the itinerary was thought through well. Our guide Riccardo was very kind and knowledgeable. It was truly a memorable and fun day.”

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14.Tuscany Comfort Day Tour from Rome with Wine & Lunch

★★★★★★★★★★5.0 · 313 reviews · 12 hours (approx.) · from $349

Review of a Rome to Florence and Tuscany day tour with high-speed rail, family winery lunch, wine tasting, and San Gimignano.

“We really enjoyed this tour. Our guide was so knowledgeable and friendly. The wine tasting tour and lunch was so much fun meeting other travelers and sharing a meal. Enjoyed shopping afterwards in Sangimigano . Only downfall was our train being delayed out of Rome so didn’t get any free time on our own in Florence but that was of no fault of the tour company. Public transportation is not always reliable. .”

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