12 Wine Tasting Day Trips in Italy to Give a Whole Day To

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

Meet Walkabout Florence Tours near Santa Maria Novella at 7:45am for an 8am departure. A professional English-speaking guide leads you through Siena, a Chianti winery lunch and tasting, San Gimignano, and Pisa. Expect a full 11 to 12 hours, plenty of walking, and optional Leaning Tower tickets.

“Beautiful scenery. The history and culture make this a must do excursion. This tour has encouraged me to return to return and spend an extended time in these lovely towns. The transportation was comfortable and timely. The guide was very knowledgeable and friendly. I highly recommend this tour and would take it again.”

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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

Travel from Florence by air-conditioned coach to Siena, San Gimignano, a family winery, and Pisa. Depending on your option, you’ll get a guided Siena walk, a three-course Tuscan lunch with wine, and free time at the Leaning Tower. Guides may include Constantino, Sara, Jacopo, or Sebastiano.

“Amazing day. We had the best time on this tour. The day is long but you see some beautiful places. Perfect if you are only staying in the area for a week.”

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3.Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

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

Spend 12 hours touring Tuscany from Rome, with guided time in Montepulciano, a farm lunch with regional wines, San Biagio Church, and free time in UNESCO-listed Pienza. Expect a scenic coach ride, walking on steep streets, and a wine tasting that may be brief in a large group.

“The lunch was mediocre at best. 5 measly sips of wine. Probably one glass of wine total. They really needed to have some bottles in the tables. The drive itself was nice and the tour guide was great.”

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4.From Florence: Siena, San Gimignano, Pisa & Lunch at Winery

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

Spend 12 hours touring Tuscany by comfortable coach, with guided Siena, free time in San Gimignano and Pisa, and an optional Chianti winery lunch. Guides such as Sara, Alessandro, and Giancarlo are known for lively local insight. Choose the Pisa Tower entry option if you want to go inside.

“We loved the interesting historical facts that Alessandro presented to us. He is an amazing tour guide with a wealth of knowledge to share. He was interesting to listen to and kept us captivated. He’s an exceptional tour guide that kept us on track and didn’t lose anyone.”

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

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

Travel from Florence by air-conditioned coach to San Gimignano, Monteriggioni, Siena, and a Chianti winery. You’ll have free time in the medieval towns, a Tuscan lunch with three wines, and optional guided visits to Siena Cathedral and the Piccolomini Library. Guides may include Sandro, Marta, or Ilaria.

“Sandro was great as our guide for all our destinations today! Highly recommend and lucky to get him!”

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6.Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch

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

Travel from Florence through Tuscany to Pisa, San Gimignano, Chianti, and Siena on a 12-hour guided day trip. You’ll see the Leaning Tower, medieval towers, Piazza del Campo, and Siena Cathedral, with optional lunch, wine tasting, and Siena guiding. Guides such as Marta, Aaron, Sandro, and Federico are praised for clear, friendly commentary.

“Best tour we had in Italy. Well planned saw a lot with plenty of rest. Very happy”

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7.Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

★★★★★★★★★★5.0 · 360 reviews · 7 hours (approx.) · from $169

Join Colin and Rachel aboard the 86-year-old wooden Andrea Jensen for a seven-hour sail from Alghero. See Capo Caccia’s cliffs, swim and snorkel in a sheltered bay, enjoy a fresh two-course lunch with wine and beer, and help raise the ship’s red sails when conditions allow.

“We had such a beautiful day with Colin and Rachel on Andrea Jensen. The trip was planned thoughtfully and I’d recommend this experience many times over to anyone planning to visit Alghero.”

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8.From Florence: Chianti Wine Tastings at Sunset Day Trip

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

Ride from Florence into Chianti in a small air-conditioned van, stopping at two family-run estates for cellar visits, six wine tastings, cheese, jam, and bruschetta. Guides such as Simone, Luigi, Alaa, and Giacomo add local insight. Choose the dinner option for a sunset meal in the Tuscan hills.

“The wine tastings at the different vineyards we went to were fantastic, and not too far outside of Florence (about 45 mins). The small group we were with (7 people total) made for a personalized experience with the staff at each vineyard. The star of the show was the 4 course and bottle of wine at dinner that was at a restaurant overlooking the Tuscan hills and sunset. The trip was approx. 7 hours total”

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9.From Florence: Ultimate Tuscany Day Trip with Wine & Lunch

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

Leave Florence with a small group of up to 14, stop at Piazzale Michelangelo, wander San Gimignano and Siena, then enjoy a family-run Chianti winery tour, multi-course lunch, and wine pairing. Guides such as Sandra, Antonio, Alma, and Anneka bring history and local tips to a full nine-hour day.

“A lovely day in Tuscany! The transportation was ideal. Our group consisted of 10 people total traveling in two vans. We loved seeing Siena and San Gimignano. The highlight however was our visit to the winery. The lunch was incredible and our host was so welcoming. We loved trying the family wines. A very special experience.”

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10.From Venice: Dolomites and Prosecco Hills Day Trip with Wine

★★★★★★★★★★5.0 · 117 reviews · from $214

Travel from Venice in a small van with an English-speaking guide to Lake Misurina, the Tre Cime peaks, Cortina d’Ampezzo, and Valdobbiadene. You get mountain views, free time for lunch, scenic stops, and a Prosecco DOCG tasting, with guides such as Simone, Francesco, and Miriam leading many departures.

“Everything was great. We really enjoyed the Proseco area, and of course we were there during the grape harvest, so it was just fascinating. Miles of vineyards loaded down with sweet ripe grapes!”

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11.Milan: Franciacorta Winery and Bergamo Day Trip with Lunch

★★★★★★★★★★4.8 · 85 reviews · from $328

Travel from Milan to medieval Bergamo, Lake Iseo, and Franciacorta in an air-conditioned minivan with Wi-Fi. Enjoy two hours in Bergamo, a three-course lunch with wine, and a guided cellar visit with two Franciacorta tastings. Guides such as Nicolò and Elia are warm, helpful, and well informed.

“This tour is extremely worthwhile. Our guide Nicolò’ was experienced and very knowledgeable. Bergamo is a quaint little town (citta’ alta) we had plenty of time to walk the streets without hassle. The lunch was superb, a three corse meal in a town along Lago d’ Iseo finally the winery tour was so interesting and the wine tasting the cherry on top. This tour is well worth doing such an enjoyable day”

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12.Florence: San Gimignano & Volterra Day Trip with Food & Wine

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

Travel from Florence through Tuscany with guide Luciana, visiting Volterra’s Etruscan sights and alabaster workshops before lunch at a winery. Continue to San Gimignano for medieval towers, Vernaccia and Chianti tasting, free time, and gelato from a world champion maker.

“Luciana was excellent. She was very knowledgeable and covered a lot in one day. Volterra and San Gimignano are beautiful and well worth a visit.”

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