Top 6 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.”

CHECK AVAILABILITY →Read our full review

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…”

CHECK AVAILABILITY →Read our full review

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!”

CHECK AVAILABILITY →Read our full review

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.”

CHECK AVAILABILITY →Read our full review

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.”

CHECK AVAILABILITY →Read our full review

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.”

CHECK AVAILABILITY →Read our full review