Top Italy Luxury Wine Tasting Custom Private Tours & Packages 2025/2026

Our 89 most popular Italy Luxury Wine Tasting Custom Private Tours & Packages trips. Compare tour itineraries from 14 tour companies. 30 reviews.

89 Trips match your criteria (1 - 22 shown)

Luxury Cycling Tour of Italy
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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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Italian Elegance: A Standard Luxury Tour
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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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Culinary Delights of Italy
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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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Italy's Hidden Gems: A Luxury Journey
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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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Culinary Delights of Italy: Rome to Florence
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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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Premium Italian Cycling Adventure
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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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Luxurious Italian Retreat
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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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Pedal Through Italy: Milan to Rome
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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 stunning scenery of the Dolomites and the rolling hills of Tuscany.
  • Explore the historic and cultural landmarks of Venice, Florence, and Rome.
  • Enjoy authentic Italian wine tastings in the heart of Tuscany.
  • Capture the essence of Italy with photography sessions in picturesque locations.
  • Experience the blend of active adventure with cultural immersion and historical exploration.

Themes

Active And Outdoor Sports, Gastronomy

What travelers are saying

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

Trip dates & details
Save this trip to your favorites or other list
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Italy Luxury Wine Tasting Custom Private Tours & Packages Reviews

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...

A

Anne

Jun 2022

Written on

We thoroughly enjoyed our day

Alessio was a fantastic guide. We thoroughly enjoyed our day ...

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