Top Italy Luxury Wine Tasting Vacation Packages 2025/2026

Our 36 most popular Italy Luxury Wine Tasting Vacation Packages trips. Compare tour itineraries from 8 tour companies. 13 reviews.

36 Trips match your criteria (23 - 36 shown)

BRAMANTE TOUR - Lake Como, Lake Maggiore, Langhe, Portofino and Milan 5 days
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Highlights

  • Lake Como, a scenery for movie lovers
  • Lake Maggiore, where art and nature come together in perfection
  • Le Langhe, vineyards and castles
  • Portofino, the classy hot spot of the Italian Riviera
  • Milan, the 2,000-years-old trendy capital of Northern Italy

Themes

Cultural, Culinary & Wine

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
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ITALY IN 10 DAYS - Venice, Florence, Rome and Amalfi
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Highlights

  • Venice, when merchants ruled the Mediterranean
  • Florence, an open-air museum
  • Pisa, how can it stand?
  • San Gimignano and Siena, power in the Middle Ages
  • Val d'Orcia, where Man and Nature blend in harmony
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Themes

Cultural, Culinary & Wine

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
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ITALY IN 2 WEEKS – THE GRAND TOURS Milan, Florence, Rome and Venice
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Highlights

  • Milan, the trendy 2,000-years-old capital of Northern Italy
  • Parma, where food is an art
  • Cinque Terre, the stunning 5 villages perched on the rocks
  • Pisa, how can it stand?
  • Florence, an open-air museum
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Themes

Cultural, Nature & Wildlife, Culinary & Wine, Relaxing Retreats

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
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Want a tailor-made trip instead?

Your trip, your way, planned by an expert:

  • You choose budget, destinations, activities, transport & lodging type
  • Expert designs the itinerary for you, and once approved, takes care of logistics
Design custom trip
ITALY IN 1 WEEK - Venice, Florence and Rome
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Highlights

  • Venice, the merchant city that ruled the Mediterranean
  • Florence, an open-air museum
  • Pisa, how can it stand?
  • Siena and San Gimignano, power in the Middle Ages
  • Val d'Orcia, the perfect blend between man and nature
Show more

Themes

Cultural, Culinary & Wine, Education / Learning

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
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ITALY IN 1 WEEK - Venice, Florence, Rome and Amalfi Coast
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Highlights

  • Venice, the merchant city that ruled the Mediterranean
  • Florence, an open-air museum
  • Siena and San Gimignano, power in the Middle Ages
  • Rome, walking in the shade of history
  • The Amalfi Coast, where divas are at home
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Themes

Cultural, Culinary & Wine

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
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ULTIMATE ITALY TOUR - Italy in 30 Days
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Balanced schedule

Highlights

  • Rome with the Coliseum and Imperial Forums, Caesars and gladiators
  • The Vatican with the Basilica of St. Peter, Popes and power
  • Orvieto and Civita, the cities “on the rocks”
  • Assisi, the birthplace of St. Francis
  • Umbria, the green heart of Italy
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Themes

Cultural, Culinary & Wine, Hiking & Walking, Photography, High Adventure

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

Trip dates & details
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Italy - Your Way
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5/5 Excellent
9 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Tours designed especially for you and your travel companions
  • Tours from $2,000 to $10,000,per person, working within your budget tofind the best options for you
  • Arranged and designed tours for all aspects or portions of your journey
  • Private and small group day tours available
  • Travel at your pace
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Themes

Cultural, Nature & Wildlife, Culinary & Wine, Family Friendly, Hiking & Walking, Local Immersion & Homestays, Birding, Train & Rail Journeys, Education / Learning, Photography, National Parks, High Adventure, Festivals & Special Events, Climbing & Mountaineering, Small Ship Cruise, Religious, Relaxing Retreats, Overland Journeys

What travelers are saying

"I've traveled to Europe several times before but not like this. Thanks to Kelley and her amazing knowledge and patience with all my queries, my famiy and I enjoyed a customized itinerary filled with a food tour in Paris and a cooking lesson in Naples, history and art lessons at the British Museum and Musee D'Orsay, with enough time to travel independently and make new discoveries with less hassle than before. I absolutely recommend the Relaxed Explorer to anyone looking to make memorable trips with their families that will be cherished by all. Thank you so much Kelley!! Would love to make more good travel memories with your help!!"

Trip dates & details
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9-DAY BOTTICELLI TOUR - Milan, Venice, Florence and Cinque Terre in 9 days
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By Vitor Italy Tours
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
21 reviews
Self-Guided / Independent Tour
Lodging level
Premium - 4 star
Physical level
Wheelchair Accessible
Trip pace
Flexible schedule

Highlights

  • Milan, the 2,000-years-old trendy capital of Northern Italy
  • Verona, the city of lovers
  • Venice, the merchant city that ruled the Mediterranean
  • Florence, an open-air museum
  • Siena and San Gimignano, power in the Middle Ages
Show more

Themes

Cultural, Culinary & Wine

What travelers are saying

"After an international trip was postponed for a third time due to COVID, my wife and I decided, last minute, to book a trip to Italy. We reached out to three self-drive tour companies, two of which - including VitorItaly - were less than half of the third quote. Ultimately we decided to go with Marcello because of his quote and responsiveness. With only a few weeks to book all of the accommodations and tours, Marcello got everything done and was very communicative throughout. We drove over 2200 km on our trip throughout Italy and Marcello booked a fantastic variety of lodgings: for example a country house near Pienza, a luxury hotel on the lagoon in Venice, and a country estate in Urbino surrounded by an organic farm and vineyard. At an olive oil mill nera Florence, we really enjoyed our time and our large order of fantastic tasting olive oil arrived yesterday. Ughetta was fantastic and gave us a great tour of their facility! Furthermore, while in Italy we could reach out to Marcello via WhatsApp and he continued to be incredibly responsive. Thanks Marcello!"

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

Health Safety

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Italy Luxury Wine Tasting Vacation Packages Reviews

J

Jay

Jun 2020

Written on

Exceptional trip

The assistance and on call service provided with Sicily Activities was exceptional. Our trip was designed around our needs and also catered for my wife’s pregnant st...

G

Georgy

Apr 2020

Written on

Best customer service ever

Best customer service ever. I had my private tour of Sicily booked for this June. Due to current pandemic crisis I was forced to cancel my trip. Sicily Activities ad...

D

Dennis

Oct 2019

Written on

Just ideal

Just what we were looking for. Small group was ideal. Nice to bond with fellow travelers. We appreciated the flexibility, especially after flight delay and lost lugg...

P

Priscilla

Oct 2019

Written on

Absolutely excellent experience

Wonderful, absolutely excellent experience with Sicily Activities Team. Pre booking assistance, 24 hours concierge during the trip and fantastic memories after tour ...

B

Bill

Sep 2019

Written on

An unbelievable vacation in Sicily

Massimo, we just wanted to thank you again for an unbelievable vacation in Sicily. Your guides are great and make the experience very personal…Our only regret from S...

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