15 Wine Country Day Trips in Italy Worth Flying For

1.Chianti Wine Region Vespa or Fiat Topolino Tour

★★★★★★★★★★4.8 · 739 reviews · 6 - 6.5 hours Our pick

Leave Florence by minivan for a guided ride through Chianti, Impruneta, and Chiocchio. Choose a 50cc Vespa, electric Vespa, Piaggio Zip, or Fiat Topolino. Guides such as Niccolò, Julia, Heather, and Yo provide scooter training, route support, and local stories before a winery visit, Tuscan meal, and wine and olive oil tasting.

“Everything from the trip to the guides and the food was great.”

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2.Prosecco Wine Region Tour with 2 Tastings

★★★★★★★★★★5.0 · 374 reviews · 6 hours (approx.) · from $204Top rated

Leave Venice at 10 a.m. for the Conegliano and Valdobbiadene hills in a comfortable minivan. Visit two wineries, taste three wines at each, enjoy a light local lunch, and learn about Prosecco from guides such as Vanessa, Francesca, Georgia, and Sebastian. The group never exceeds eight, making this a relaxed half-day escape.

“The views of the hills and mountains were gorgeous and just as wonderful as the Prosecco! Vanessa was so knowledgeable and educated us throughout the day and in between visits. Because we had a group of 7 it was like a private tour!”

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3.Private Tuscany Tour from Florence Including Siena, San Gimignano and Chianti Wine Region

★★★★★★★★★★4.5 · 128 reviews · 8 hours (approx.) · from $520

Travel from Florence by private Mercedes with a driver such as Placido, Christian, Julian, or Valentine. Explore Siena and San Gimignano at your own pace, then follow the Chiantigiana wine road. Add a winery tasting and farmhouse lunch if you want. Hotel pickup, WiFi, and return transport are included.

“Wonderful guide and friend. He was the most charming gentleman who made us so comfortable. Would really recommend him.”

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4.From Rome: Frascati Wine Region Tour with Wine Tasting

★★★★★★★★★★4.8 · 53 reviews · from $167

Ride from Rome to a 300-year-old family winery in Frascati with a private driver and English-speaking guide. Walk through the vineyards, visit the old cellars, taste local wines with olive oil and oven-baked bread, then return to your hotel. Guides may include Patrick, Eleonora, or Massimiliano.

“We thoroughly enjoyed our visit to this destination, creating a truly memorable experience. The transportation was smooth and comfortable, thanks to our skilled guide, Patrick. Our host at the vineyard showcased extensive knowledge and a genuine passion for their work. Every detail appeared carefully considered, resulting in a delightful and relaxing atmosphere. We wholeheartedly recommend this experience to anyone seeking a peaceful escape from the city.”

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5.Private daytrip to Siena & Chianti wine country, with wine tasting from Florence

★★★★★★★★★★5.0 · 43 reviews · 8 hours (approx.) · from $467

Spend about eight hours with a private English-speaking driver exploring Greve, Panzano, a Chianti winery, and Siena. Taste Chianti Classico, Riserva, Super Tuscan wines, and olive oil, with lunch optional. Drivers such as Mario, Donatello, Thommas, and Giuseppe have adapted routes to suit each group.

“Our driver Donatello was great! He suggested a wonderful iteneriary that allowed us to see a few places that we wanted that weren’t even part of the tour. He was so knowledgeable and personable, it really made the day. We loved Sienna. And the meal and wine tasting at Casa Emma was very good.”

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6.Private Tuscany Wine Country Day Trip from Rome with Lunch

★★★★★★★★★★4.5 · 36 reviews · 11 hours (approx.) · from $1,067

Leave Rome early in a Mercedes with an English-speaking driver-guide and spend the day among Tuscany’s hill towns and vineyards. Visit Montepulciano, Bagno Vignoni, Montalcino, and Pienza, with wine tastings and a Tuscan lunch of cold cuts, cheeses, and bruschetta. Guides may include Max, Roberto, Giancarlo, or Khan.

“Wonderful scenic tour. Thoroughly enjoyed the Tuscan countryside. Enjoyed the winery! Nice to be in a small group throughout the day, gives more individual attention. Just one of the stops had a very steep climb to meet the Guide. Just needed more of a warning about the steepness for people who may have health conditions that a climb like this can affect.”

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7.Small group Chianti Classico & Brunello wine region from Siena

★★★★★★★★★★5.0 · 31 reviews · 5 hours 30 minutes (approx.) · from $198

Leave Siena at 2 pm for a small-group afternoon through Chianti Classico and Montalcino. With a maximum of six people, you visit a family-run organic winery, taste Chianti with pecorino, cured meats, olive oil, and balsamic vinegar, then see Montalcino or choose a second Brunello tasting. Guides such as Morad and Stephanie add local detail.

“Our driver, Murad, was exceptionally friendly and informative - he was able to share videos of Palio di Sienna during the drive. Highly recommend!!”

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8.Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

★★★★★★★★★★5.0 · 28 reviews · 8 hours (approx.) · from $430

Spend about eight hours with a private driver exploring San Gimignano and the Chianti wine region from Florence. Marco, Lorenzo, Sam, or Tomasso may tailor the day to your interests, with possible winery visits, countryside viewpoints, Volterra, or the Florence American Cemetery. Pickup and drop-off are included.

“Our private tour was customized by Marco, the owner, through email correspondence. We left all the details to him and we weren't disappointed.”

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9.Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Florence

★★★★★★★★★★5.0 · 10 reviews · 8 hours (approx.) · from $413

Leave Florence at 9 a.m. with Marco or another local driver in a private, air-conditioned minivan. Visit medieval San Gimignano, follow the Chiantigiana road, and arrange winery tastings or lunch in the Chianti hills. You get hotel pickup, flexible attention, and an eight-hour day without a group bus.

“A great introduction to the chianti region. Beautiful. And Marco was super nice, helpful and informative. San Gimignani was very unique and the wine experience at Casa Emma was fantastic. Whatever you want to do in Tuscany - I highly recommend working with Marco!”

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10.from Rome Montepulciano and Montalcino, the Wine Routes

★★★★★★★★★★4.5 · 9 reviews · 8 to 9 hours (approx.) · from $135Best value

Leave Rome at 7:30 am for Montepulciano and Montalcino on an English-language coach tour. Explore both hill towns, taste DOCG wines in a 13th-century cellar, eat a traditional Tuscan lunch, and enjoy free time for views and local shops. Guide Giovanni is part of the experience.

“An unforgettable tour through the heart of Tuscany’s wine country! The views were spectacular, and the wines were among the best I’ve ever tasted. Would go again in a heartbeat.”

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11.From Milan: Langhe Wine Region Day Trip with Barolo Tasting

★★★★★★★★★★4.8 · 8 reviews

Leave Milan from Porta Garibaldi for a 10-hour trip into Piedmont. You’ll visit Barolo from April to October or Alba from November to March, taste six wines at a family-run winery, and stop at Grinzane Cavour Castle. English-speaking guides such as Sara Calabrese and Barbara lead the day, with small groups available.

“The day was fantastic. The tour guide, Sara Calabrese was wonderful. She insured that everyone was taken care of. Was respectful and courteous. A lot of energy and fun to be around. Always made herself available if we had questions, even those not directly related to the tour. I am glad it was a small group of 7. So much more enjoyable than the large groups. The driver did an excellent job in getting us from place to place in comfort. What really set them apart from others is that I wear a prosthetic on my left leg. She and the driver insured they dropped me off close to my…”

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12.From Roma: Montepulciano and Montalcino, on the Wine Routes

★★★★★★★★★★5.0 · 8 reviews

Travel from Rome to Montepulciano and Montalcino with a live English or Spanish guide. Walk medieval streets, visit a 13th-century cellar with an Etruscan tomb, taste two wines, and enjoy cold cuts, cheeses, bruschetta, and pici al ragù. Expect a full day with moderate walking and no hotel pickup.

“An unforgettable tour through the heart of Tuscany’s wine country! The views were spectacular, and the wines were among the best I’ve ever tasted. Would go again in a heartbeat.”

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13.LANGHE : Vespa Tour to the Wine Region of Barolo

★★★★★★★★★★4.8 · 8 reviews

You’ll self-drive an electric Vespa through Piedmont’s Langhe wine country, stopping in La Morra, Barolo, and Monforte d’Alba. Staff at Pollentia explain the scooter, provide a route book, charging kit, phone holder, helmet, and remote support. Lunch and wine tasting are optional extras, and a driving license is required.

“Everything was perfect. The autonomy (there were 2 of us) of the vehicle was more than sufficient for the proposed tour that touched all the destinations we had set ourselves with the addition of a couple of detours. Beautiful experience”

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14.Private tour from Livorno port to Chianti Wine Region

★★★★★★★★★★5.0 · 5 reviews · 9 hours (approx.) · from $591

Meet your English-speaking driver at Livorno port at 8:30 a.m. and ride in a private Mercedes-Benz to San Gimignano and the Chianti hills. You’ll have free time in the medieval town, photo stops along country roads, and the option of wine tasting or lunch at a winery. Guides such as Soni, Sonny, and Aldo have adjusted routes and timing for cruise schedules.

“This tour was amazing! Our guide catered to what we were wanting to see and chose some wineries for us to visit that really had an amazing experience to go along with the wonderful wine tastings. I will say just as a heads up that one of the wineries they visit only takes cash and no cards for the lunch tasting. Thankfully we had cash to cover it but we were close. The food served at both wine tastings we visited was superb and worth every penny! Definitely recommend this tour!!”

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15.private trip to Sirmione Lake Garda & Valpolicella Wine Region

★★★★★★★★★★5.0 · 4 reviews · from $341

Travel from Verona in a private, air-conditioned minivan with a certified English-speaking driver. Cruise Lake Garda by private boat from Sirmione toward Garda and Punta San Vigilio, then visit a Valpolicella winery for a producer-led tour and Amarone tasting. Lunch is not included, but restaurant reservations can be arranged.

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