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ToursEuropeItalyItaly Wine Tasting Trips & Packages

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 (1 - 22 shown)

Italy, Sicily Grand Tour: See & Experience it ALL in 12 Days, 1st Class Custom Tours
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Italy, Sicily Grand Tour: See & Experience it ALL in 12 Days, 1st Class Custom Tours

By Charlie The Traveler
Local Expert
Verified by Travelstride as locally operated and in the top of their field for customer reviews, local knowledge, and safety.
5/5 Excellent
100+ reviews
Small Group Tour
Why we love them
Travelers report that traveling with CharlieTheTraveler is a life-changing experience, in the best possible way.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Cooking Class at a Local’s Home
  • Exploring 3 of Southern Italy’s Prettiest Towns
  • Swimming in Clear Water Alongside a White Cliff
  • Boat Rides to Exotic Islands Just Off the Coast of Sicily
  • Hiking Around a Mighty Volcano
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Themes

Culinary & Wine, Local Immersion & Homestays

What travelers are saying

"Thank you for reaching out! This trip was absolutely phenomenal—truly the best 10 days of my life. I’m incredibly grateful for everything you arranged. Cindy, in particular, took such good care of me. It felt like she was supporting me around the clock, and I really appreciate her dedication. I’m already eager to recommend your services to my friends and colleagues. On top of that, I realized how much I love the South Island—I’m hoping to visit Queenstown and Mount Cook National Park next, perhaps while participating in some business-related community events. I’d be thrilled if your company could help me plan that trip as well. Thank you again for everything. I look forward to traveling with you in the future!"

Trip dates & details
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12 days From$3,954

Health Safety

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Luxury Cycling Tour of Italy
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Luxury Cycling Tour of Italy

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Cycle through the breathtaking landscapes of Tuscany and Val d'Orcia.
  • Enjoy exclusive wine tastings in the famous Chianti region.
  • Capture stunning photographs of Italy's picturesque countryside.
  • Experience luxury accommodations and fine dining throughout the journey.
  • Explore the historic and cultural landmarks of Rome on two wheels.

Themes

Luxury, Active And Outdoor Sports

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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8 days From$4,389
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Italian Elegance: A Standard Luxury Tour
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Italian Elegance: A Standard Luxury Tour

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Indulge in Milan's world-renowned shopping and fine dining.
  • Savor exclusive wine tastings in Italy's celebrated vineyards.
  • Experience the opulent lifestyle and cultural treasures of Venice and Florence.
  • Explore the historic and luxurious facets of Rome with style.
  • Enjoy a seamless blend of cultural immersion and luxury experiences.

Themes

Cultural, Luxury

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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16 days From$8,786
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Culinary Delights of Italy
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Culinary Delights of Italy

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Exclusive wine tastings in Rome, Florence, and Venice
  • Private cooking sessions with renowned Italian chefs
  • Luxury dining experiences in Italy's top gourmet destinations
  • Visits to iconic landmarks like the Colosseum and Grand Canal
  • Personalized service and guidance throughout the tour

Themes

Cultural, Gastronomy, Luxury Travel

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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11 days From$17,600
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Italy's Hidden Gems: A Luxury Journey
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Italy's Hidden Gems: A Luxury Journey

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Explore the vibrant streets and historical richness of Bologna.
  • Capture the breathtaking beauty of Cinque Terre's colorful coastal villages.
  • Savor unique wines and scenic views in Italy's picturesque landscapes.
  • Uncover the ancient allure of Matera's cave dwellings.
  • Dive deep into the cultural and historical tapestry of Palermo.

Themes

Cultural Immersion And History, Unique Experiences

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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11 days From$6,038
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Culinary Delights of Italy: Rome to Florence
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Culinary Delights of Italy: Rome to Florence

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Private wine tasting sessions in Rome's historic vineyards
  • Hands-on cooking classes with master Italian chefs
  • Exclusive meals at Michelin-starred restaurants in Florence
  • Guided tours of local markets and specialty food shops
  • Luxurious accommodations with gourmet dining experiences

Themes

Cultural, Luxury, Gastronomy

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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7 days From$3,838
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Premium Italian Cycling Adventure
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Premium Italian Cycling Adventure

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Cycle through iconic cities including Milan, Florence, Siena, and Rome
  • Exclusive wine tasting sessions in Tuscany's renowned vineyards
  • Photography opportunities in picturesque landscapes
  • Explore rich historical sites and cultural landmarks on two wheels
  • Enjoy premium accommodations and authentic Italian cuisine

Themes

Active And Outdoor Sports, Cultural Immersion And History

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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12 days From$6,586
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Luxurious Italian Retreat
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Luxurious Italian Retreat

By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Unwind with top-tier spa treatments and gourmet dining in Rome.
  • Savor the rich flavors of Tuscany with exclusive wine tasting sessions.
  • Embrace tranquility through guided yoga and meditation in Florence.
  • Explore the romantic waterways and luxurious comforts in Venice.
  • Rejuvenate your senses along the stunning Amalfi Coast.

Themes

Luxury, Wellness, Cultural

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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10 days From$5,486
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Italy Wine Tasting Trips & Packages Reviews

All Italy Wine Tasting Trips & Packages, expedition cruises, self guided adventures and vacation packages. Find the best guided and expert planned vacation and holiday packages. Read more about Italy Wine Tasting Trips & Packages

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...

Tour:  Italy, Sicily Grand Tour: See & Experience it ALL in 12 Days, 1st Class Custom Tours

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.

Tour:  The Italy Grand Tour

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...

Tour:  The Italy Grand Tour

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 ...

Tour:  Wine and Food Tasting Weekend

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...

Tour:  Wine and Food Tasting Weekend

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