Top 8 Wine Tasting Day Trips from 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

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.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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4.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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5.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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6.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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7.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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8.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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