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6 Wine Tasting Day Trips in Italy Worth the Early Start

6 day trips  ·  from $77 a head

This is the shortlist you would send a friend: 6 wine tasting day trips in Italy worth a free day, each with its price and the one thing to know before the pickup.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Meeting the coach near Santa Maria Novella
Day Trips, Day Trips from Florence, Day Trips from Italy, Day Trips with Lunch, Tour Reviews, Wine Tasting Day Trips, Wine Tasting Day Trips in Florence, Wine Tasting Day Trips in Italy

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

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 an English-speaking guide. Walk through Siena and enter its cathedral, eat lunch and taste four wines at Fattoria Poggio Alloro, explore San Gimignano, then visit Pisa. Guides such as Alex, Sara, Davide, and Manolo are frequently assigned.

“Our tour guide was very informative and she kept us all on time. We saw all of the sites and the lunch at the winery was delicious and the views were spectacular.”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - A Tuscan winery lunch worth the time
Day Trips, Day Trips from Florence, Day Trips from Italy, Day Trips with Lunch, Tour Reviews, Wine Tasting Day Trips, Wine Tasting Day Trips in Florence, Wine Tasting Day Trips in Italy

Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

2.Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing

★★★★★★★★★★4.5 · 6,006 reviews · 12 hours (approx.) · from $78

Set out from Florence at 7:30 a.m. for Siena, San Gimignano, and Pisa. Choose a guided Siena visit and a three-course winery lunch with wine pairing, then enjoy free time in the hill towns and at Pisa’s Square of Miracles. Guides such as Constantino, Sara, Jacopo, and Simone have been praised for clear timing and friendly help.

“It is a wonderful tour and the price is reasonable. Make sure you return in time as the bus will leave without you!”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - San Biagio and the church beneath the hills
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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

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

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

Spend about 12 hours traveling from Rome to Montepulciano and Pienza with an English-speaking guide. Walk Montepulciano, visit San Biagio, eat a three-course farm lunch, taste Tuscan wines, and enjoy free time in UNESCO-listed Pienza. The group is capped at 25, with private and small-group upgrades available.

“Thank you Anna and Pablo! We had a wonderful time in the country side. Anna was very knowledgeable and Pablo was an excellent driver.”

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From Florence: Siena, San Gimignano, Pisa & Lunch at Winery - Siena: a guided start in the medieval heart
Day Trips, Day Trips from Florence, Day Trips from Italy, Day Trips with Lunch, Tour Reviews, Wine Tasting Day Trips, Wine Tasting Day Trips in Florence, Wine Tasting Day Trips in Italy

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

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

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

Spend 12 hours exploring Tuscany by comfortable coach, with a guided Siena walk, free time in San Gimignano and Pisa, and an optional organic winery lunch with four regional wines. Guides such as Sara, Alessandro, and Giancarlo are known for lively storytelling. Choose the lunch option for the most memorable part of the day.

“Really enjoyed the tour! Sara was knowledgeable and authentic and definitely displayed a love of her homeland. She was great with English and our limited Italian. Sara was very thoughtful of our comfort and answered questions of all on the tour! It was an excellent experience!”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - San Gimignano and the town of towers
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

Leave Florence at 8 a.m. for San Gimignano, Monteriggioni, a Chianti winery, and Siena. You get free time in the medieval towns, a three-course Tuscan lunch, three wines plus vin santo, and optional guided Siena and cathedral visits. Expect a full 11 hours, plenty of hills, and a large-group format.

“Sandro and Fabi were fantastic, well organised and very informative. Great meal and wine tasting too! Even the rain couldn't dampen the mood.”

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Florence: Pisa, Siena, S. Gimignano, Chianti Wine & Lunch - Meeting at Piazzale Montelungo
Day Trips from Florence, Day Trips from Italy, Day Trips with Lunch, Tour Reviews, Wine Tasting Day Trips, Wine Tasting Day Trips in Florence, Wine Tasting Day Trips in Italy

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

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

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

Travel from Florence to Pisa, San Gimignano, Chianti, and Siena in 12 hours with a multilingual guide such as Marta, Aaron, Sandro, or Federico. You get free time in Pisa and San Gimignano, a Siena walking tour, and optional lunch with three wines and Vin Santo. Expect beautiful views, long bus rides, and a brisk schedule.

“Federico and Fernando did awesome job taking care of the group!”

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More ways to spend the day

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