Top Italy Wine Tasting Trips & Packages In 2025/2026

Our 247 most popular Italy Wine Tasting Trips & Packages trips. Compare tour itineraries from 71 tour companies. 106 reviews.

247 Trips match your criteria (67 - 88 shown)

Private Sicily Romantic Week Tour
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5/5 Excellent
18 reviews
Vacation / Holiday Package
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Enjoy enchanting romantic trip following some of the famous love stories.
  • Visit the most picturesque Sicilian towns with breathtaking sea coasts
  • Stay in extremely romantic boutique hotels where heart beats faster
  • Spend relaxing pool & cocktail day in colorful Etna countryside
  • Treat your body and soul to romantic Spa & Wellness
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Themes

Cultural, Nature & Wildlife, Culinary & Wine, National Parks

What travelers are saying

"Wonderful Godfather Tour with Antonio. He was charming, very professional, spoke excellent English and was very informative. It was a brilliant day out. I highly recommend doing this tour with Antonio, you won’t be disappointed."

Trip dates & details
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From East to West Sicily Tour
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5/5 Excellent
18 reviews
Private Guided
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Visit world famous monuments and little -known corners of Sicily’ s most stunning towns
  • Get a full immersion to reach history, traditions and culture of island
  • Be always accompanied by local guides who know it best
  • Experience Sicily through its gastronomy, wines, art and music
  • Get an authentic lifestyle e experience and feel like you’ve lived in Sicily the whole life

Themes

Cultural, Culinary & Wine

What travelers are saying

"Wonderful Godfather Tour with Antonio. He was charming, very professional, spoke excellent English and was very informative. It was a brilliant day out. I highly recommend doing this tour with Antonio, you won’t be disappointed."

Trip dates & details
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Health Safety

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Private Sicily Countryside Week Tour
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5/5 Excellent
18 reviews
Vacation / Holiday Package
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Stay in authentic luxury resorts located in wonderful Sicilian countryside
  • Discover best Sicilian towns such as Taormina, Syracuse, Noto, Ragusa and Modica
  • Learn cooking tricks being surrounded by lemon trees and taste the best Sicilian wines
  • See volcano craters and try organic Etna products: olives, cheeses, tomatoes, mushrooms
  • Explore Sicily off beaten pathes and meet locals who keeps its secrets

Themes

Nature & Wildlife, Culinary & Wine, Hiking & Walking

What travelers are saying

"Wonderful Godfather Tour with Antonio. He was charming, very professional, spoke excellent English and was very informative. It was a brilliant day out. I highly recommend doing this tour with Antonio, you won’t be disappointed."

Trip dates & details
Save this trip to your favorites or other list

Health Safety

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Taste of Italy
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4.5/5 Excellent
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Bologna:Explore one of the most food-centric cities in Italy, where Bolognese sauce was invented. Sistine Chapel:Marvel at Michelangelo's incredible fresco work on the ceiling that has been newly restored to showcase the vibrant colors. Orvieto:Step into the mysteries and culinary traditions of this ancient walled city that rises above the surrounding landscape. Florence:Fall in love with the capital of beautiful Tuscany, the birthplace of the Renaissance.

Themes

Cultural, Culinary & Wine

What travelers are saying

"We used CIE for an amazing tour of Ireland. The food and the locals were amazing. Here is my issue: we were told that another CIE tour from Scotland would be joining us in Dublin. The majority of those travelers had some type of respiratory virus and joined our tour. Tour director knew they were sick as she pointed out pharmacies at every tour stop. Every scheduled breakfast, lunch or dinner was restricted to certain tables since we had limited reserved seating and that virus spread like wildfire among the original Dublin travelers. My understanding is that CIE has a policy that “sick” passengers are not permitted on the tour. My wife got the “sickness” and I got COVID. Ruined such an amazing place. I placed a customer service ticket with CIE on 21 May 2014 and have heard nothing back. I will probably see Bigfoot before a response."

Trip dates & details
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Taste of Italy with Sorrento
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4.5/5 Excellent
100+ reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Isle of Capri:Enjoy the breathtaking sights and the scenic views of sparkling lapis and turquoise-hued waters on the Isle of Capri. Pompeii:See this perfectly preserved ancient Roman city, which was buried in the ash of Mount Vesuvius nearly two thousand years ago. Gondola Ride in Venice:Explore the incredible Venetian architecture as you wander through its romantic canals. The Vatican, with the Sistine Chapel & St Peter’s Basilica:Tour the world's largest church and Michelangelo's magnificent Sistine Chapel frescoes in the Holy See. Roman Colosseum & the Forum:Visit the impressive ruins of the centers of ancient Roman life.

Themes

Cultural, Culinary & Wine

What travelers are saying

"We used CIE for an amazing tour of Ireland. The food and the locals were amazing. Here is my issue: we were told that another CIE tour from Scotland would be joining us in Dublin. The majority of those travelers had some type of respiratory virus and joined our tour. Tour director knew they were sick as she pointed out pharmacies at every tour stop. Every scheduled breakfast, lunch or dinner was restricted to certain tables since we had limited reserved seating and that virus spread like wildfire among the original Dublin travelers. My understanding is that CIE has a policy that “sick” passengers are not permitted on the tour. My wife got the “sickness” and I got COVID. Ruined such an amazing place. I placed a customer service ticket with CIE on 21 May 2014 and have heard nothing back. I will probably see Bigfoot before a response."

Trip dates & details
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Best of Sicily (Off-Season) in 11 Days Tour
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5/5 Excellent
23 reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Explore Monreale
  • Visit Ancient Greek site of Segesta
  • Experience Syracuse Ortygia island neighborhood walk
  • Explore Neapolis Archaeological Park

Themes

Cultural, 50 Plus, Hiking & Walking, Transformative

What travelers are saying

"We purchased two backpacks from Rick Steves Europe. One of them arrived damaged and unusable. Their website says that you must contact them if you receive damaged merchandise. I have attempted to email them through their website and I have left 3 voicemails (nobody answers the phone, ever!) and nobody has contacted me back. At this point, it seems like I've been ripped off. Buyer beware. Extremely disappointed."

Trip dates & details
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Best of Italy in 17 Days Tour
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5/5 Excellent
23 reviews
Group Tour
Lodging level
Standard - 3 star
Physical level
Moderate
Trip pace
Full schedule

Highlights

  • Enjoy cruising in Lake Como by ferry
  • Visit South Tyrol Museum of Archaeology andFlorence's Accademia Gallery
  • Discover Orvieto City and San Brizio Chapel tour
  • Explore Colosseum tour
  • Visit Vatican Museum & Sistine Chapel

Themes

Cultural, Nature & Wildlife, 50 Plus, Hiking & Walking, National Parks

What travelers are saying

"We purchased two backpacks from Rick Steves Europe. One of them arrived damaged and unusable. Their website says that you must contact them if you receive damaged merchandise. I have attempted to email them through their website and I have left 3 voicemails (nobody answers the phone, ever!) and nobody has contacted me back. At this point, it seems like I've been ripped off. Buyer beware. Extremely disappointed."

Trip dates & details
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My Way: Europe in 14 Days Tour
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5/5 Excellent
23 reviews
Small Group Tour
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Visit the Notre-Dame Cathedral and exquisite Sainte-Chapelle
  • See the brilliantly lit Eiffel Tower and enjoy a twilight ride to the top
  • Explore Paris, one of the world's most thrilling cities!
  • You will have great time in the Berner Oberland's magnificent Lauterbrunnen Valley, flanked by towering
  • Experience rolling hills of beautiful Burgundy and climb the high into the heart of the Swiss Alps

Themes

Cultural, Nature & Wildlife, National Parks

What travelers are saying

"We purchased two backpacks from Rick Steves Europe. One of them arrived damaged and unusable. Their website says that you must contact them if you receive damaged merchandise. I have attempted to email them through their website and I have left 3 voicemails (nobody answers the phone, ever!) and nobody has contacted me back. At this point, it seems like I've been ripped off. Buyer beware. Extremely disappointed."

Trip dates & details
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Italy Wine Tasting Trips & Packages Reviews

A

Amy D.

Dec 2024

Written on

everything was amazing.

We will never travel without Charlie and his crew. It...

J

John B

Sep 2024

Written on

We had a great time.

We had a great time. The trip was well organized by Alma Italia and the guides were excellent.

W

William R.

Jul 2024

Written on

Tim and Alessio were amazing!

Tim and Alessio were amazing! Our family had a wonderful time in Rome, Sorrento, Capri and the Amalfi coast! The trip was seamless; planes, trains, and automobiles m...

K

Kristi

Nov 2022

Written on

Our trip to Italy exceeded our expectations!

Our trip to Italy exceeded our expectations! Alessio was amazing to work with and was always available to answer questions we had before and during our trip. It was ...

E

Eugene

Nov 2022

Written on

Had a wonderful time seeing Tuscany

Had a wonderful time seeing Tuscany with Alessio. Great experiences, great sightseeing and great education due to Alessio's knowledge and connections. Would recommen...

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