WINE TOURS · WINE COUNTRY DAY TRIPS IN ITALY

15 Wine Country Day Trips in Italy, Priced and Compared

29 tours  ·  from $48 a head

The 15 best wine country day trips in Italy you can book right now, each with its price, its length and the kind of afternoon it turns into. The first one is first for a reason.

Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery - Siena Cathedral is worth the guided entry
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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 guided Siena and cathedral visits, free time in San Gimignano and Pisa, and a family-run winery lunch with four wine tastings. Guides such as Alex, Sara, Davide, and Manolo are known for clear directions, humor, and good pacing. Choose the Pisa tower upgrade if you want to climb.

“I had a fantastic experience with this tour guide Sara and Milano from start to finish. Everything was well-organized, smooth, and thoughtfully planned, which made the entire tour stress-free and enjoyable. Sara was knowledgeable, engaging, and passionate, sharing interesting facts and stories that really brought the place to life. Sara also very friendly, patient, and happy to answer all my questions. The pacing was perfect, and I never felt rushed, while still getting to see and learn so much. Overall, it was a truly memorable experience, and I am so glad I chose this operator. Highly recommended for anyone looking for a professional, informative, and enjoyable tour!”

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Pisa, Siena and San Gimignano Day Trip with Lunch & Wine Pairing - A Tuscan winery turns lunch into an attraction
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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

Leave Florence at 7:30 a.m. for Siena, San Gimignano, and Pisa with an English-speaking tour escort. Choose guided Siena access and a winery lunch with Tuscan wine, then enjoy free time in the medieval towns. Expect a full 12 hours, a group of up to 63, and plenty of walking.

“Great tour, saw so much and the scenery just breathtaking. The bus was comfortable and the stops one better than the next. Highly recommend the tour.”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting - Montepulciano: wine town with a serious uphill walk
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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wine Tasting

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

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

Spend about 12 hours touring Tuscany from Rome by air-conditioned coach. Walk through Montepulciano, visit San Biagio, eat a three-course farm lunch with wine, then browse Pienza. English-speaking guides such as Flavio, Barbara, Anna, and Antonino lead the day, with small-group upgrades adding extra tastings and a Montalcino castle visit.

“This was the best experience ever!! Beautiful countryside tour. Outstanding authentic food. Erica and Barbara were great guides. Could not have asked for a better experience”

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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting - Chianti wine and the midday meal
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San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch & Wine Tasting

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

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

Spend about 11 hours touring Tuscany by coach, with free time in San Gimignano and Monteriggioni, guided sights in Siena, and a winery lunch with three wines plus vin santo. Choose the Siena walking tour and cathedral option for added art and history. Guides may include Sandro, Marta, Alessandra, or Ilaria.

“Great experience with an opportunity to see a lot! My only recommendation would be that if you have the cathedral guided tour, have it start when you arrive in Sienna so you have a little bit more free time.”

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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines - The early ride through central Italy
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Rome: Tuscany & Montepulciano Day Trip with Lunch & Wines

5.Tuscany & Montepulciano Day Trip with Lunch & Wines

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

Spend 11 to 12 hours traveling from Rome to Tuscany with an English-speaking guide, visiting Montepulciano, San Biagio, and Pienza. You’ll walk medieval streets, eat a three-course vineyard lunch, and taste local wines, including Brunello di Montalcino. Guides such as Antonino, Anna, Eduardo, and Barbara are known for lively stories and practical help throughout the day.

“Fanatic tour guide was very well clued up. Every stop was magnificent and the food was amazing”

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Siena, San Gimignano and Chianti Wines Day Tour from Florence - Starting at Piazzale Montelungo in Florence
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Siena, San Gimignano and Chianti Wines Day Tour from Florence

6.Siena, San Gimignano and Chianti Wines Day Tour from Florence

★★★★★★★★★★4.5 · 2,542 reviews · 10 hours 30 minutes (approx.) · from $78

Travel by air-conditioned coach from Florence to Monteriggioni, Siena, San Gimignano, and a Chianti estate. You’ll get guided time in Siena, free time in the hill towns, and a tasting of two or three wines with local snacks. Guides such as Alex, Jacopo, Gabrielle, and Constantino have earned strong praise for clear organization and good humor.

“Everything was organized perfectly. Jacob and Camilla were great and were very knowledgeable of the sites we saw. The wine tasting was awesome and we enjoyed all of the wine that was served. Would highly recommend to anyone visiting Florence to go on this day trip”

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Amalfi Coast Day Tour from Sorrento with Light Lunch and Wine - Positano: steep streets and postcard views
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Amalfi Coast Day Tour from Sorrento with Light Lunch and Wine

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

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

Travel from Sorrento in a Mercedes minivan with up to eight people, stopping in Positano, Amalfi, and Ravello. You get about an hour in each town, a light three-course lunch with wine, and local commentary from drivers such as Enzo, Nello, Antonio, or Marcella. A boat trip from Amalfi may be available for an extra €20.

“This is a family run business and it was very informative. The olive oil and cheese were excellent. The ride up to where they make the cheese was interesting to say the least Wear sneakers or walking shoes. Lots of cobblestones”

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Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines - Montalcino and the first Brunello tasting
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Full Day Tour to Val d’Orcia and Gladiator’s Fields with Wines

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

Spend about 11.5 hours touring Montalcino, Pienza, and Montepulciano from Florence. You’ll taste Brunello and Vino Nobile, sample pecorino, admire the Madonna di Vitaleta chapel, and pass the Gladiator filming area with guides such as Tabatha, Giovanni, or Sebastiano.

“The tour is long, and you spend a lot of time in a bus, but it is well worth it. The towns you visit are so amazing and the Val d’Orcia is beautiful. On top of that, we got to taste some good wine. My family enjoyed it:”

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From Rome: Bagnoregio & Orvieto Day Trip with Wines & Lunch - The coach ride is part of the bargain
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From Rome: Bagnoregio & Orvieto Day Trip with Wines & Lunch

9.Bagnoregio & Orvieto Day Trip with Wines & Lunch

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

Spend 12 hours visiting Civita di Bagnoregio and Orvieto from Rome, with a Tuscan farmhouse lunch and five-wine tasting near Montepulciano. Guides such as Chiara, Laura, Alberto, and Semih are praised for clear history and practical help. Expect long coach rides, steep walks, and a full but rewarding day.

“Barbara was an excellent guide. Very warm and welcoming. She made us feel like family.”

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Tuscany Day Trip: Chianti & Cooking Class Small Group - Castellina in Chianti: a quick taste of village life
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Tuscany Day Trip: Chianti & Cooking Class Small Group

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

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

Spend about 11.5 hours exploring Castellina, Monteriggioni, San Gimignano, and Certaldo from Florence. The day includes a hands-on Tuscan cooking class, lunch, dessert wine, two wine tastings, and free time in medieval towns. Guides such as Marco and Marta have earned special praise for their warm, helpful approach.

“This was a small group tour. I would recommend to purchase tickets for Siena sites ahead of time so that you save time and not stand in cues. The wine tasting and lunch at Poggio ai Laghi in Monterioggioni was so much fun and the views at San Gimignano were spectacular.”

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From Florence: Chianti Hills Half-Day Tour with Wine Tasting - Walking through the vines and learning the basics
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From Florence: Chianti Hills Half-Day Tour with Wine Tasting

11.Chianti Hills Half-Day Tour with Wine Tasting

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

Travel by air-conditioned Gran Turismo bus from Santa Maria Novella station to Chianti, where you walk among vines, visit a vinegar cellar, taste seven wines, vin santo, olive oils, cheeses, cold cuts, and seasonal Tuscan specialties. Guides such as Chiara, Emma, and Jordano have led recent departures, but staff can vary.

“We had a great experience. Thanks to our wonderful guide Chiara who told us important facts about the region and everything you need to know about Tuscan wine. She cared a lot about the wellbeing of the whole group for the trip and went above and beyond to make it perfect for everyone. Our driver Toto was also very skilled and we had a safe and relaxed bus journey. You can consider yourself lucky when you are making this tour with them!”

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Taormina: Guided Etna Wine Tasting Half-Day Tour - Linguaglossa and the short village pause
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Taormina: Guided Etna Wine Tasting Half-Day Tour

12.Guided Etna Wine Tasting Half-Day Tour

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

From Taormina, ride an air-conditioned coach through Etna villages to Gambino Winery near Linguaglossa. Your guide, often Isabella or Simona, explains Sicily, Etna, and local wine before four tastings with cheeses, olives, bread, vegetables, and olive oil. Expect beautiful views, a cellar visit, and a relaxed five-hour outing.

“Our guide was fantastic, never stopped giving information from the moment we left Taormina all the way to the winery. Very knowledgable on the surrounding villages and the history of Sicily. She spoke Sicilian, French and English - switching seamlessly which was impressive. The winery is beautiful, and our semelier was incredibly knowledgable on the wines, the history of the winery and the family that built it. We enjoyed some lovely wines and fantastic pairings. The value for money was superb! A great afternoon out, would highly recommend!”

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Florence: Siena & San Gimignano Day Trip with Lunch & Wine - Siena in two hours: medieval streets and a guided introduction
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Florence: Siena & San Gimignano Day Trip with Lunch & Wine

13.Siena & San Gimignano Day Trip with Lunch & Wine

★★★★★★★★★★4.6 · 426 reviews · from $84

Spend nine hours in Tuscany, traveling by air-conditioned coach from Florence to Siena, an organic winery, and San Gimignano. A local guide leads the Siena walk, while free time lets you explore both medieval towns. The day includes a three-course lunch, wine pairings, four Tuscan wines, Wi-Fi, USB charging, and bottled water.

“Wonderful tour. Thank you so much to Nathan, our tour guide, for accompanying us so well. We had such a wholesome time with good company throughout. I learnt lots about Italy and I feel a lot closer to my Italian routes now ☺️🇮🇹 I will always remembers Nathan’s brilliant and humour on the bus which made the travel aspect enjoyable! I would highly recommend this tour and Nathan as your guide (and Alessandro as our fabulous bus driver!)”

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From Taormina: Full-Day Etna, Wine & Alcantara Canyons Tour - From Taormina to Etna’s high slopes
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From Taormina: Full-Day Etna, Wine & Alcantara Canyons Tour

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

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

Travel from Taormina in a small group with guides such as Riccardo, Daniele, Nicola, Tony, or Roberto. Hike Etna’s extinct craters at 2,000 meters, enter a lava cave, eat at a local winery, taste Etna wines, and stop at the Alcantara Canyons. Boots, jackets, equipment, transport, lunch, and entrance fees are included.

“We were a small group of six, which made it easy to get along and everyone was very helpful. Our guide Roberto was excellent...very friendly,informative,and very well equipped with all is needed. Sure to recommend to friends”

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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine - Leaving Alghero for the Coral Riviera
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Sailing day trip on Tall Ship Andrea Jensen with Lunch and Wine

15.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 gaff ketch Andrea Jensen for a seven-hour sail from Alghero. You’ll see Capo Caccia’s cliffs, swim and snorkel in a quiet bay, enjoy a fresh two-course lunch with wine and beer, and help raise the ship’s red sails when conditions allow.

“Great trip. Lots of room. Antipasti food course excellent. Best bit is the scenery and sailing back to port. Will come again.”

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New in Wine Country Day Trips in Italy

★ 4.5Private Day Tour & Lunch: Parmesan, Wine, and Vinegar TastingFrom $22232 reviews
★ 4.7San Gimignano & Volterra Day Trip with Food & WineFrom $32757 reviews
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★ 4.8Full-Day Pompeii & Wine Tasting TourFrom $14777 reviews
★ 4.8Franciacorta Winery and Bergamo Day Trip with LunchFrom $32885 reviews
★ 4.5Civitavecchia: Tuscany Full-Day Guided Trip w/Wine TastingFrom $24369 reviews
★ 5.0Wineries, Tastings, Lunch & San Gimignano Day TripFrom $22382 reviews
★ 4.4Day Tour in a Vintage Fiat 500 with WineryFrom $14641 reviews

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