Top 12 Wine Tasting Day Trips in Italy

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 full-day Tuscany trip from Florence to Siena, San Gimignano, Pisa, and a Chianti winery lunch with wine tasting.

“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 12-hour Tuscany day trip from Florence to Siena, San Gimignano, and Pisa, with winery lunch, wine pairing, and practical tips.

“A great way to see the highlights of Tuscany if you are staying in Florence! We chose to do the guided Siena tour and lunch at the vineyard and it was well worth it. Siena and San Gimignano are real gems and the lunch at the vineyard is a great way to see the countryside. The bus stops a little far from the Piazza in Pisa but there is an optional transportation service if you don’t want to walk. Also, Sara our tour guide was very informative and entertaining as well as keeping the itinerary organized. My only complaint is that some of the stops can feel quick but you…”

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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 coach travel, Tuscan lunch, wine tasting, Pienza, costs, tips, and honest drawbacks.

“Loved this tour. This was our second tour of Tuscany this trip. This tour was more focused on the small towns and countryside of Tuscany than wine but the winery we visited was amazing considering it was a 16th century friary still operated through generations of the same family. Eduardo was the best tour guide. Thanks for an amazing day!”

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4.Siena, San Gimignano, Pisa & Lunch at Winery

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

See Siena, San Gimignano, Pisa, and Chianti from Florence, with a winery lunch, wine tasting, guided visits, and comfortable coach travel.

“Excellent trip, our guide Genevra was fabulous and our driver Giuseppe was fantastic. Would definitely recommend this trip.”

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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

See San Gimignano, Monteriggioni, Siena, and Chianti in one long Tuscan day with a winery lunch, wine tasting, and coach transport.

“Beautiful towns, gorgeous food and lovely hosts! The tour started on time and it was well organised. The bus was very comfortable with free wifi and plugs for you to charge your phones. Our hosts were very accommodating and attentive to our needs. Many thanks to AARON and LILY for being our guide and to PLACIDO for driving us to our destinations safely.”

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

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

Review of the Florence to Pisa, San Gimignano, Siena and Chianti day trip, with lunch, wine tasting, timings, value and practical tips.

“We had a wonderful time, honestly, couldn’t have been better. We saw so much, never felt rushed, and experienced more of Italy than we would have on our own. Thank you so much Marta, Frederica, and Ferdinand.”

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7.Chianti Wine Tastings at Sunset Day Trip

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

Review of the Chianti sunset wine tour from Florence, with two family wineries, six tastings, Tuscan scenery, dinner, costs, and practical tips.

“This tour was absolutely worth every penny! With only six people in our group, it felt like a private, relaxed experience. The setting was breathtaking—rolling hills, golden light, and vineyards as far as the eye could see. We visited a charming family-run winery, tasted exceptional wines, and learned so much about the winemaking process. The hosts were welcoming and passionate, and the views during sunset were straight out of a postcard. It was the perfect blend of beauty, wine, and conversation. Highly recommend for anyone looking for an authentic and peaceful Tuscan experience.”

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8.Ultimate Tuscany Day Trip with Wine & Lunch

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

Review of a small group Tuscany day trip from Florence to Siena, San Gimignano, and Chianti with a family winery lunch.

“It was a very full day and Antonio was knowledgeable about everything! He was charming and funny and made the most of our day by talking with us in the van and all along the way. Seeing the city view from Michelango's piazza was a great start to the day. We enjoyed hearing about the history of Siena and were blown away by the food and wine pairing at lunch! San Gimigniano is a beautiful city and the 3 items on this tour were the real trifecta! Excellent tour - highly recommend!”

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9.Dolomites and Prosecco Hills Day Trip with Wine

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

Escape Venice for the Dolomites, Lake Misurina, Cortina, and Prosecco Hills, with small-group transport, mountain views, and DOCG tasting.

“Fun activity to get out of the city for the day! Simone was great! Very funny and informative! Great way to see multiple cities and lakes and the Prosecco hills were gorgeous! Highly recommend :)”

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10.Franciacorta Winery and Bergamo Day Trip with Lunch

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

Tour Franciacorta’s sparkling wines, Bergamo’s medieval walls, Lake Iseo, and a traditional lunch on a full-day trip from Milan.

“My tour guide was amazing, Nicolo was great, very nice”

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11.San Gimignano & Volterra Day Trip with Food & Wine

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

Review of Florence’s San Gimignano and Volterra day trip, with Tuscan lunch, winery visits, gelato, guided walks, and practical tips.

“Fast paced, covered a lot of historical, cultural and gastronomic information of the area.”

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12.Tuscany Chianti Winery Private Day-Trip with Lunch

★★★★★★★★★★5.0 · 20 reviews · 6 hours · from $258

Explore Greve, Montefioralle, Chianti wine and olive oil on a private Tuscany day trip from Florence with a Tuscan lunch.

“Mr Paolini was the perfect tour guide. We were educated on wine and olive oil and I was amazed by his knowledge. We learned so much and had the BEST wine and lunch. Beautiful scenery!!!”

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