Top Italy Wine Tasting Tours - page 2

Siena, San Gimignano and Chianti Wines Day Tour from Florence

10 hours 30 minutesFree Cancellation

4.6

(3,115)

from $76

Spend a day sipping one of Italy’s top wines, Brunello di Montalcino, on this trip from Siena to Montalcino. Travel first to a small winery to explore the vineyards and cellars and taste the famous Rosso and Brunello di Montalcino wine. Then, visit a family-run winery in Montalcino, where you tour the grounds and sit down for a classic Tuscan meal with more wine. Visit the Abbey of Sant'Antimo before tasting even more wine at your third and final winery of the day.

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

9 hoursFree Cancellation

The Tuscan region of Chianti is known for its wine, but sussing out the best wineries on your own can take hours of research. Skip the hassle and head straight to three hand-picked wineries to tour the wine cellars and taste different varietals on this group wine tour from Florence. Midday, treat your senses to a light lunch of fresh regional products like bruschetta, handmade pasta, cheese, and salami. You'll also travel through the Tuscan countryside dotted with vineyards, olive groves, and villas, stopping to explore the traditional village of Greve.

(1,005)

from $222

Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner

8 hoursFree Cancellation

Explore the Tuscan countryside during a full-day tour from Florence with horseback riding. Your guide provides a gentle horse and riding gear, then leads you through the vineyards, olive groves, and rolling hills of the Chianti region. Afterward, visit the medieval town of San Gimignano, and enjoy a typical Tuscan light lunch with a wine pairing. Option available to substitute a farm tour for the horseback ride if desired.

(1,449)

from $174

Horseback Ride, visit S.Gimignano, Lunch wine Tasting &much more

7 hoursFree Cancellation

Experience a different side of Sicily on a full-day tour to Mt. Etna, the largest active volcano in Europe. Your guide shares informative commentary about the history, geology, and wildlife of Mt. Etna as you take nature walks, tour a cave created by lava flows, and see old volcanic craters. Select from hiking or cable car options to customize your visit, then end the day by visiting a wine cellar to sample the local vino. Includes hotel pickup and drop-off from Catania.

(469)

from $222

Mt Etna and Wine tasting tour from Catania

Mt Etna and Wine tasting tour from Catania

8 hoursFree Cancellation

Savor Florence's celebrated cuisine on an evening food tour featuring Florentine steak and Tuscan wine. Explore the vibrant districts of Oltrarno and Santo Spirito, making stops at five carefully selected foodie hotspots. With 14 delicious tastings—including tomato bruschetta, two paccheri pasta dishes, and a sit-down Tuscan dinner—this experience offers a flavorful escape from typical tourist traps.

(344)

from $124

Likely to Sell Out

Sample Authentic Bistecca alla Fiorentina known for its unique flavor and thick cut!

Florence Evening Food Tour with Florentine Steak & Tuscan Wine

3 hours 30 minutesFree Cancellation

There’s much more to Italian food than pizza and pasta, and this Venice tasting tour offers a delicious introduction to Venetian cuisine. Instead of visiting the typical tourist bars, get an insider’s perspective on where the locals drink and dine in the city, sampling an array of Veneto specialties. Fresh seafood, homemade gelato, traditional Venetian cookies, and regional wines are all on the list.

(558)

from $79

Eat Like a Local: Venice 3-Hour Small-Group Food Tasting Tour

2 hours 30 minutes to 3 hours 30 minutesFree Cancellation

Food Tasty and History Tour in Civitavecchia

(3,748)

from $103

Cooking classes in Rome can vary when it comes to the participation element, but this one is fully hands-on for an immersive experience. Under the guidance of an Italian chef, prepare multiple dishes—fresh fettuccine, ricotta ravioli, and tiramisu—entirely from scratch. Conclude with a sit-down meal of the dishes created during the session, with wine and limoncello to wash it all down.

(289)

from $79

Rome 3 in 1 Cooking Class: Fettuccine, Ravioli & Tiramisu

Siena: A Wine Tour and Tasting Experience

(8,911)

from $61

Spend a day in the beautiful Tuscan countryside sipping wine and making new friends. Visit authentic wineries for tours and generous tastings of world-famous varietals like Chianti Classico and Super Tuscan. Learn about wine production and flavor profiles, and round out your palate with samplings of high-quality balsamic vinegar and olive and truffle oils. Also, visit the charming medieval village of San Gimignano for free time to explore the winding streets and artisan shops.

(389)

from $99

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

7 hoursFree Cancellation

Classic Half-Day Wine Tour in Frascati with Lunch

(1,133)

from $178

5 hoursFree Cancellation

Venice: Hands-On Pasta & Gelato Class with Wine by St Mark's

(153)

from $105

Taormina is one of the most spectacular cities in Sicily, but its crowds and heat can be daunting. Take a break with this half-day sailboat cruise along the coastline to admire highlights like the bays of Spisone and Mazzarò, Blue Grotto, and Isola Bella. Drop anchor to swim and snorkel in the turquoise waters or relax on board with drinks and snacks while learning about the local history and lore.

(89)

from $104

Sailing Tour Taormina Bay

Take a deep dive into Italy’s most beloved bubbly and the area where it’s produced with this small-group Prosecco wine tour. Depart from Venice and take in the gorgeous countryside on your way to a family-run winery that produces prestigious DOCG Prosecco. Enjoy a guided tour through the vineyards and cellars and learn about this sparkling wine’s production and history, then relax over a tasting paired with traditional cheeses and charcuterie.

4.6

(143)

from $82

Small Group Prosecco Experience from Venice or Treviso

Small Group Prosecco Experience from Venice or Treviso

4 hoursFree Cancellation

Price varies by group size

(131)

from $169

Bologna Food Experience: Factory tours & Lunch By Italian Days

The Bologna food region is one of the most famous in Italy, but finding the best producers to visit on your own takes hours of research. On this culinary tour, visit local and family-run producers most tourists miss for a behind-the-scenes look at the creation of Parmigiano-Reggiano cheese, Modena balsamic vinegar, prosciutto, and wine. Enjoy samples along the way, and indulge in breakfast and a multi-course Italian lunch with wine pairings.

Bologna Food Experience: Factory tours & Lunch By Italian Days

9 hoursFree Cancellation

Take a break from sightseeing and head to the hills surrounding Lucca to sample the area’s excellent wines. Connect with a winemaker at a boutique winery for a relaxed private tour through the vineyards and cellar, with plenty of time to ask questions about the history and production of the local vintages. Then relax on the terrace overlooking the rolling countryside to sample the estate’s wines and olive oil while enjoying the view.

(1,270)

from $209

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

Lucca: Wine Tasting Experience - Tenuta Adamo Winery

1 hour 30 minutesFree Cancellation

Get to know Rome's popular Trastevere neighborhood through its food and wine—and discover bites and restaurants you'd otherwise miss—on this half-day walking tour. With just a small group for company, visit local-favorite venues for multiple tastings, including cheese, ham, pizza, pasta, and aged balsamic vinegar. Explore Trastevere’s cobblestone streets between sampling local wines and beers. Save room for the tour’s final bite: traditional gelato.

(439)

from $23

Special Offer

Rome: Trastevere Luxury Food tour with Free-Flowing Fine Wine

Rome: Trastevere Luxury Food tour with Free-Flowing Fine Wine

4 hoursFree Cancellation

Likely to Sell Out

Rome Food Tour: Hidden Gems of Trastevere with Dinner & Wine

Delve into the world of Puglian wine without leaving Lecce’s old town with this wine tasting experience in the heart of the Baroque city. Take a break from sightseeing and relax at a local wine bar for a guided tasting featuring four different regional wines paired with local specialties. Learn about Puglia’s winemaking history and culture as you sip and enjoy views over the pretty lane lined with traditional “palazzi”.

(1,492)

from $68

Wine and Food Tasting Experience in Lecce old town

Wine and Food Tasting Experience in Lecce old town

1 hour 30 minutesFree Cancellation

4.6

(109)

from $35

Special Offer

Half day Chianti Vineyard Escape from Florence with Wine Tastings

5 hoursFree Cancellation

Likely to Sell Out

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

Tuscany is notable for its food, wine, and scenery, but exploring the region in a limited time isn’t easy. Enjoy a stress-free sampler of locations in the captivating Val d’Orcia region on this full-day tour from Rome. With a guide at your side, visit the wine town of Montepulciano, have lunch surrounded by vineyards, explore the historic center of Pienza, and relax on the return journey to Rome.

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

12 hoursFree Cancellation

4.7

(5,499)

from $99

Price varies by group size

From Florence: Chianti Wine Experience with Tastings & Views

Chianti is home to the scenic wine country and notable cellars, but getting there on unfamiliar rural roads on your own can be challenging. This group wine tour takes you to two different wineries in the Tuscan hills to explore the vineyards and their cellars, as well as relax over guided tastings. Sip local reds and whites, plus sample balsamic vinegar and extra-virgin olive oil, while enjoying views over the Chianti countryside.

From Florence: Chianti Wine Experience with Tastings & Views

5 hours 30 minutesFree Cancellation

4.4

(840)

from $41

Rome by Night - Ebike Small Group Tour - Food and Wine (Option)

4 hoursFree Cancellation

Price varies by group size

(1,318)

from $69

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What are people saying about Italy

Rome: Award Winning Trastevere Group Food Tour with Wine

Michele_f, Jul 2026

Our family of four...

Our family of four enjoyed this food tour! It was a great way to try a variety of local foods, along with some delicious wine and beer. The rest of the group were pretty awesome too! Everything was well organized, and we loved getting to sample so many different flavors. Come hungry—we were definitely full by the end of the tour!

Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner

Allie_H, Jul 2026

What an incredible wine...

What an incredible wine tasting tour! We had the absolute best time from start to finish. Our guide, Leo, was exceptional—friendly, knowledgeable, and made the entire experience so much fun. He kept the day organized while making everyone feel relaxed and welcome. The wineries were fantastic, and the whole experience exceeded our expectations. If you’re considering this tour, don’t hesitate! Highly recommend, and we’d absolutely do it again.

Siena, San Gimignano and Chianti Wines Day Tour from Florence

Veronique_P, Jun 2026

Exceptional and Great value !

Fantastic FULL Day and reasonably priced for everything we did ! Superb organization both before the trip ( always with Viator booking and communication ) and Ciao Florence the tour operator ! Our 2 Guides Carmella & Anna were outstanding and Driver Boris just perfect ! Only comment is I wish I had known it was such a big group ( 78 people on the bus !) staff ran a very smooth tour THANK YOU ! Wine tasting was superb and fun , and all the stops worth it ! ( only wish passengers would tip the staff !! They sure deserve it , only a few of us did )

Full Day Tour to Val d'Orcia and Gladiator's Fields with Wines

Evelyn_C, Jun 2026

Great tour of Val D'orcia

I saw Val D'orcia's pictures on lot of travel magazines, always wanted to see it in person, so signed up this tour. The tour operation Ciao Florence has very big operation, lots of people at meeting point. But they are super organized, with color coded stickers for different groups. The whole day tour was great, I got to see all the beautiful places in the travel magazine. The green rolling hills, tall cypress trees, movie Gladiator's villa (cannot go in private property, only peep from the gate), 2 wine tasting. One is the most expensive wine in Italy in Montalcino. Guide is very organized about meeting point, but is comfortable. Would highly recommend this trip!

Florence Evening Food Tour with Florentine Steak & Tuscan Wine

Stephen_C, Jun 2026

Florence wine and food tour recommended

Wonderful experience, our guide was very informative, friendly and a local who passed on his knowledge on Florence culture, history, and Tuscan food, like a friend we had known for years. The food and drink were top quality, the evening passed in a whirl , The joining instructions and location were simple ,totally recommended.

Bologna Food Experience: Factory tours & Lunch By Italian Days

Steve_R, Jun 2026

Fun and Informative Food Tour

Julia was a wonderful guide: informed, clear, professional, patient, and fun. Roberta, our driver and general tour assist was just as lovely. These women truly care about creating an enacting and friendly tour experience for all and they could not have done a better job! I found the Parmagiano Reggiano production facility most interesting, as we were able to see several, real production steps happen up close in real time. I was a bit skeptical when I discovered on the bus that lunch incuded karaoke - which is not for me - but it was really a lot of fun, and more of a light DJ’d experience with the staff singing and all of us joining in. The best part of that was seeing how much the staff (and chef!) seemed to enjoy leading the tour group in song. Their enthusiasm was infectious and honestly it was really warm and lovely to see. The breakfast and lunch was very good, and both the Balsamico and Prosciutto stops were also nice. Overall, it was a very good tour and a lot of fun!

Tuscany Wine Tour: 2 Wineries & San Gimignano from Florence

Elizabeth_H, Jun 2026

One of my favorite...

One of my favorite experiences in Tuscany! It's also a great hot weather activity. It was 95F the day I did the tour, but the van had great AC. The first vineyard has a fantastic view -- you're outside, but in the shade and it's earlier in the day. The second vineyard is inside with great AC. All the hosts were welcoming, helpful, and generous with the wine. Couldn't recommend more (esp as a solo traveler).

Etna Countryside Food & Wine Lovers Tour (Small Group or Private)

Dyanne_D, Jun 2026

Wine Tasting - Mount Etna

This wine tasting touring was awesome. It was around a hour drive with beautiful views from Taormina where we were staying. Our tour guide, Orazio, was amazing. He was friendly, knowledgeable, and made the whole experience feel easy. Gave us great background on the area, the wine, and Mount Etna without making it feel like a lecture. The wineries were beautiful, the wine was incredible, and the views around Etna were unreal. Could not recommend this experience enough. If you’re in Sicily and enjoy a little bit of drinking, this is absolutely worth doing.

Tuscany in One Day: Pisa, Siena, San Gimignano & Chianti Lunch

Michele_C, Jun 2026

Overall, it is a...

Overall, it is a well-organized, jam-packed tour. We did feel a little rushed to be back on time to move on to the next town. We usually like these tours to get an overview and then return at our own leisure to explore further. If you are expecting more than 1.5 hrs to explore each area, I would keep searching or limit your tour to only 2 towns. Siena was our favorite.

Wine Experience In Chianti Hills from Florence

Leah_W, Jun 2026

Great experience meeting point not clear

The Wine tasting was lovely however the meeting point was not clear at all - it’s tucked away. Other tours I’ve been on the meeting point was at the bus parking lot (where our guide actually led us to) and that was actually easier to find than meeting in the station. I would suggest someone waiting out of the ticked away place with a clear flag as it was a stressful start to the trip and also meant as a couple we couldn’t sit together on the bus.

San Gimignano, Siena, Monteriggioni, Chianti Day Trip with Lunch

SharynSmith, May 2026

A dream fulfilled.

This tour was well run and the guide very informative and friendly. She was doing the tour in 2 different languages which gets a bit hard. The places visited were fantastic and the Tuscan lunch and wine tastings were fun. Our only complaint was that the bus was absolutely freezing where we were sitting so we had to endure being chilled to the bone for hours on end. I wasn’t feeling well and this compounded it. We asked if the driver could alter the temperature but it didn’t seem possible as the top deck were hot. Overall an exhausting and enjoyable day.

Wine Experience: vineyard, wines and food

Patricia_V, Apr 2026

Delicious wines in a charming setting

If you go here in the beginning of April, dress warmly! Host supplied blankets for all, but it was quite cold. Temperature aside, the host was engaging and entertaining. The vineyard is set in an idyllic area and the building is an absolutely charming trulli house. The wines were very good..along with the champagne. Snacks were provided between each tasting, and they were all made on site. The whole experience was a delight and the ride to get to the vineyard was beautiful through the countryside. I highly recommend this experience, but dress warmly!