Italy Luxury History Custom Private Tours & Packages Tours & Trips

62 Italy Luxury History Custom Private Tours & Packages trips. Tours from 14 tour companies. 51 reviews.

62 Trips match your criteria (1 - 20 shown)

Italy (Sicily): See & Experience it ALL in 7 Days, 1st Class Custom Tours
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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
Premium - 4 star
Physical level
Moderate
Trip pace
Full 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
  • Hiking Around a Mighty Volcano
  • Structures Designed by Greeks Thousands of Years Ago
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Themes

Education / Learning, Hiking & Walking, Festivals & Special Events

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!"

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The Italy Grand Tour
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Venice Lose yourself in the labyrinth of alleyways and canals. Venice is a place of alluring charm and elegance like no other.
  • Florence Marvel at the grandeur of the architecture in the Renaissance capital of Italy and soak up the atmosphere of the most artistic and culturally rich city in the world.
  • Rome The eternal city, a cinematic dream and the heart of the mighty Roman empire and modern day Italy
  • Naples An enigmatic place of history and glamour mixed with a hint of danger makes Naples a very exciting place to explore.
  • Capri and the Amalfi Coast Explore the villages of the iconic Amafli coast, the classic Italy summer coastal retreat.

Themes

Nature & Wildlife, Culinary & Wine

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

Trip dates & details
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Wine and Food Tasting Weekend
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Wine tasting in Chianti
  • wine cellars
  • Pool day Wine and food tasting

Themes

Cultural, Culinary & Wine

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

Trip dates & details
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Custom Designed Trip
Lodging level
lodgingLevelName
Physical level
N/A

Highlights

  • Fully customized trip based on preferences
  • Matched with a local specialist
  • From $150 per person per day
Self-Guided / Independent Tour
Rome and Tuscany Tour
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Explore the heart of Rome visiting some of the MUST SEE icons of the city such as the Coliseum and Roman Forum
  • Enjoy organic Italian delights such as Pecorino Romano cheese or freshly made pasta
  • Enjoy a smooth ride in the stunning Tuscany countryside
  • Enjoy this magical place by immersing yourself in one of the natural bathtubs

Themes

Nature & Wildlife, Culinary & Wine

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

Trip dates & details
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Classic Italy Tour
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Explore the history of the city to life recounting the fascinating stories of your surrounding
  • Explore the spectacular region surrounding Venice
  • Exploring the enthralling Vatican Museums
  • A wine tasting and a gourmet lunch at a family run vineyard

Themes

Cultural, Nature & Wildlife

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

Trip dates & details
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The Amalfi Coast And Her Islands Private Tour
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Naples Lose yourself in the labyrinth of alleyways in historic Naples. Naples is an enigmatic place of history and glamour mixed with a hint of danger like no other.
  • Amalfi Coast coastal drive Explore the villages of the Amalfi coast and experience a road trip along one of the most iconic stretches of coastal roads in the world.
  • Pompeii Take an adventure into the past on a guided visit to this remarkable palace preserved under volcanic ash for thousands of years.
  • Capri, Ischia and Procida Vacation like a celebrity island hopping around these movie star islands

Themes

Cultural, Nature & Wildlife

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

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Gourmet Food & Fine Wine Tuscany Tours
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Swim in the stunning outdoor pool with a panoramic hilltop view overlooking the Chianti scenery
  • Enjoy a full-day tour that combines a cooking class and wine tasting
  • Enjoy a traditional Tuscan dinner in a trattoria in Florence
  • Enjoy cycling at your own pace on peaceful country lanes

Themes

Nature & Wildlife, Culinary & Wine

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

Trip dates & details
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Tuscany Photography Retreat
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Private Guided
Why we love them
They focus on creating unique and exclusive experiences including one of a kind private tours, tastings of rare wines and local cuisine.
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Discovering the beauty and heart of Italian culture
  • Learn philosophy of our Italian Photography workshop
  • Explore some of the richest jewels of Renaissance art and architecture
  • Take a tour of their cleverly designed cellar, hidden in the hill of the vineyard

Themes

Culinary & Wine, Photography

What travelers are saying

"We had a trip of a lifetime. Tim was very flexible in handling the planning of the itinerary. I wanted this to be a special trip for myself and my husband to celebrate our milestone birthdays and have always wanted to visit Italy to experience the sights, culture, food and warmth of the people. Tim was cognizant that my husband’s knees were not the best and so advised on the hotel proximities to the activities and events with that in mind. He also understood that I wanted to do this trip in as cost effective manner as possible and so was flexible when it came to allowing me to utilize our RCI points to book hotels and just advised on location. Tim passed the baton over to Alessio when it came to executing on the itinerary and Alessio did a marvelous job despite the time crunch given the trip was still within busy season of end of Sept - beginning of Oct. A week before the trip, my husband fell and damaged his knee but luckily was able to address this with an orthopedic doctor and we were able to proceed on our dream trip. We visited Rome, Sorrento, Pompeii, Capri island, Amalfi Coast, Florence and Lucca and experienced many of the activities and sites through private tours arranged through Amal Italia with the most knowledgeable, accommodating guides who worked together with the transfer personnel to make it all happen seemlessly. On trips to the Vatican, Uffizi Gallery and Pompeii as examples, the tour guides knew exactly how to condense the time spent to focus on the key highlights, telling the history while linking the intricacies and nuances of the artifacts being shown. Whether it was booking a cooking class in Sorento, visit to a vineyard, spa massage in Pompeii or a dinner overlooking the sea, Alessio did his utmost best to make this truly a memorable experience. We would not have been able to cover half the activities on our itinerary were it not for the very professional, flexible, knowledgeable and accommodating help on logistics and events through Amal Italia. Thank you Tim and Alessio for a once in a lifetime experience!"

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Italy Luxury History Custom Private Tours & Packages Reviews

B

Beth Kennedy

Feb 2023

Written on

This tour was super fun!

This tour was super fun! CharlieTheTraveler is a great company to book with if you’re looking for an organized trip that saves you time in planning. Sicily was a pre...

M

Michelle Wylder

Feb 2023

Written on

This was my first time booking with an independent tour company, and I did not regret it.

This was my first time booking with an independent tour company, and I did not regret it. Charlie is an expert at creating unforgettable experiences through his tour...

P

Patti Olson

Feb 2023

Written on

This Sicily tour with CharlieTheTraveler was amazing!!

This Sicily tour with CharlieTheTraveler was amazing!! Loved the itinerary, the guides were amazing, and the whole process was efficient and smooth. I definitely app...

S

Sofia Rueda

Feb 2023

Written on

I’m so glad I decided to book this trip at the last minute, it was so much fun.

I’m so glad I decided to book this trip at the last minute, it was so much fun. I particularly liked visiting the various towns in Sicily, I loved learning about the...

M

Marleen Page

Feb 2023

Written on

CharlieTheTraveler was an excellent company to travel with.

CharlieTheTraveler was an excellent company to travel with. My family and I loved everything included in this Sicily tour, we couldn’t have asked for better. The who...

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