Top Italy Luxury History Custom Private Tours & Packages 2025/2026

Our 62 most popular Italy Luxury History Custom Private Tours & Packages trips. Compare tour itineraries from 14 tour companies. 51 reviews.

62 Trips match your criteria (23 - 44 shown)

Highlights of Northern and Central Italy
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By Viandando Luxury Travel
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
6 reviews
Private Guided
Why we love them
They listen carefully to what each traveler wants and work hard to make their Italian vacation dreams a reality- no matter how complex.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Full schedule

Highlights

  • Visit the islands of Murano and Burano; discover Verona the city of Romeo and Juliet
  • Explore Lake Como, renowned for its palatial villas, rose-laden belvederes and majestic Alpine vistas
  • Visit Milan one of the fashion capitals of the world;
  • Enjoy our Underground Tour of the Colosseum

Themes

Cultural, Culinary & Wine

What travelers are saying

"We just returned from a two-week trip that took us from Venice, to Parma, to Florence, to Rome, and Sorrento, and we couldn't be happier with the trip set up by everyone at Viandando. After telling them what our interests were, they set up a tour that introduced us to Italy and kept everyone in our group (ranging from grandparents to kids) engaged and excited. All of the guides we had were friendly, engaging, and knowledgeable. Although Italy was packed with tourists, Viandando set us up so we never waited in any lines and were able to experience some of the top sites without huge crowds. The hotels we had were all fantastic, offering us great rooms and central locations to explore the city. Our drivers were waiting for us and got us where we needed to be on time! Most importantly, Elena, Eleonora, and Giulia were there for us when plans changed unexpectedly. Our flights were cancelled multiple times and, even though this was totally out of their control, Viandando had our back and was able to make last minute travel changes to help save whatever they could of the days that we lost due to our flights. Their support while we were on the trip was absolutely fantastic. If you're looking for a quality company to set up a first-class trip, you can stop searching--Viandando will get it done for you!"

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Grand Tour of Abruzzo
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By Viandando Luxury Travel
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
6 reviews
Private Guided
Why we love them
They listen carefully to what each traveler wants and work hard to make their Italian vacation dreams a reality- no matter how complex.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Discover Santo Stefano in Sessanio
  • Visit of Sulmona
  • Visit Castelvecchio

Themes

Cultural, Culinary & Wine

What travelers are saying

"We just returned from a two-week trip that took us from Venice, to Parma, to Florence, to Rome, and Sorrento, and we couldn't be happier with the trip set up by everyone at Viandando. After telling them what our interests were, they set up a tour that introduced us to Italy and kept everyone in our group (ranging from grandparents to kids) engaged and excited. All of the guides we had were friendly, engaging, and knowledgeable. Although Italy was packed with tourists, Viandando set us up so we never waited in any lines and were able to experience some of the top sites without huge crowds. The hotels we had were all fantastic, offering us great rooms and central locations to explore the city. Our drivers were waiting for us and got us where we needed to be on time! Most importantly, Elena, Eleonora, and Giulia were there for us when plans changed unexpectedly. Our flights were cancelled multiple times and, even though this was totally out of their control, Viandando had our back and was able to make last minute travel changes to help save whatever they could of the days that we lost due to our flights. Their support while we were on the trip was absolutely fantastic. If you're looking for a quality company to set up a first-class trip, you can stop searching--Viandando will get it done for you!"

Trip dates & details
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Unconventional Sicily
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By Viandando Luxury Travel
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
6 reviews
Private Guided
Why we love them
They listen carefully to what each traveler wants and work hard to make their Italian vacation dreams a reality- no matter how complex.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Visit Palermo
  • Discover Enna and Calascibetta
  • Visit Prestigious Winery
  • Relaxing at your lovely masseria

Themes

Cultural, Culinary & Wine

What travelers are saying

"We just returned from a two-week trip that took us from Venice, to Parma, to Florence, to Rome, and Sorrento, and we couldn't be happier with the trip set up by everyone at Viandando. After telling them what our interests were, they set up a tour that introduced us to Italy and kept everyone in our group (ranging from grandparents to kids) engaged and excited. All of the guides we had were friendly, engaging, and knowledgeable. Although Italy was packed with tourists, Viandando set us up so we never waited in any lines and were able to experience some of the top sites without huge crowds. The hotels we had were all fantastic, offering us great rooms and central locations to explore the city. Our drivers were waiting for us and got us where we needed to be on time! Most importantly, Elena, Eleonora, and Giulia were there for us when plans changed unexpectedly. Our flights were cancelled multiple times and, even though this was totally out of their control, Viandando had our back and was able to make last minute travel changes to help save whatever they could of the days that we lost due to our flights. Their support while we were on the trip was absolutely fantastic. If you're looking for a quality company to set up a first-class trip, you can stop searching--Viandando will get it done for you!"

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Grand Tour of Sicily
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By Viandando Luxury Travel
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
6 reviews
Private Guided
Why we love them
They listen carefully to what each traveler wants and work hard to make their Italian vacation dreams a reality- no matter how complex.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Visit Palermo
  • Explore Erice and the Saltpans
  • Visit The Greek Ruins of Selinunte
  • Discover Noto and Siracusa

Themes

Cultural, Culinary & Wine

What travelers are saying

"We just returned from a two-week trip that took us from Venice, to Parma, to Florence, to Rome, and Sorrento, and we couldn't be happier with the trip set up by everyone at Viandando. After telling them what our interests were, they set up a tour that introduced us to Italy and kept everyone in our group (ranging from grandparents to kids) engaged and excited. All of the guides we had were friendly, engaging, and knowledgeable. Although Italy was packed with tourists, Viandando set us up so we never waited in any lines and were able to experience some of the top sites without huge crowds. The hotels we had were all fantastic, offering us great rooms and central locations to explore the city. Our drivers were waiting for us and got us where we needed to be on time! Most importantly, Elena, Eleonora, and Giulia were there for us when plans changed unexpectedly. Our flights were cancelled multiple times and, even though this was totally out of their control, Viandando had our back and was able to make last minute travel changes to help save whatever they could of the days that we lost due to our flights. Their support while we were on the trip was absolutely fantastic. If you're looking for a quality company to set up a first-class trip, you can stop searching--Viandando will get it done for you!"

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Charming Matera and Apulia Private Tour
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5/5 Excellent
51 reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Visit the enchanting city of Matera
  • Explore the Trulli of Alberobello,a Unesco Site
  • Taste the authentic Apulian cuisine and local wine
  • Discover the pictureque village of Polignano a Mare
  • Enjoy a lunch in a traditional Trullo in Alberobello

Themes

Cultural, Culinary & Wine

What travelers are saying

"Both the Sicily tour and the week in Malta were wonderful. The tour guide in Sicily who took us around Palermo and to Monreal was very knowledgeable, especially in the Cathedral.The guide who took us through the Greek temples was also super interesting and personable. The driver, Francesco, who took us to the Roman house spoke very good English and took time to point out a lot of things we would have missed otherwise. All of the hotels in Sicily were nice but the one in Agrigento was really special.I am glad we skipped the wine tasting the day of Mt. Etna and Taormina because we wouldn't have been able to see much of Taomina otherwise. Sicily is so big you can't see everything in a week but I think your tour does a great job of hitting the highlights. It was great. The tour in Malta was even better. Malta is a fascinating place but what made it really great was having Charmaine as our tour guide. She did a really exceptional job of explaining and showing her country to us. She is knowledgeable, enthusiastic and fun to be with. She really took care of us. I wish she could be my guide on every trip I take. I really like staying in Sliema for two nights and then two nights in Valletta to get two different perspectives of the city. The hotel in Gozo was delightful. I am telling everyone I know to go to Malta and get Charmaine as their tour guide"

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Private Gourmet Wine Tour in Tuscany
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5/5 Excellent
51 reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Visit medieval towns like San Gimignano and Siena
  • Taste the world known Brunello di Montalcino
  • Enjoy panoramic views onto Chianti Hills Discover the charming Tuscany's countryside
  • Try the authentic Tuscan's specialties and fiorentina steak

Themes

Cultural, Culinary & Wine

What travelers are saying

"Both the Sicily tour and the week in Malta were wonderful. The tour guide in Sicily who took us around Palermo and to Monreal was very knowledgeable, especially in the Cathedral.The guide who took us through the Greek temples was also super interesting and personable. The driver, Francesco, who took us to the Roman house spoke very good English and took time to point out a lot of things we would have missed otherwise. All of the hotels in Sicily were nice but the one in Agrigento was really special.I am glad we skipped the wine tasting the day of Mt. Etna and Taormina because we wouldn't have been able to see much of Taomina otherwise. Sicily is so big you can't see everything in a week but I think your tour does a great job of hitting the highlights. It was great. The tour in Malta was even better. Malta is a fascinating place but what made it really great was having Charmaine as our tour guide. She did a really exceptional job of explaining and showing her country to us. She is knowledgeable, enthusiastic and fun to be with. She really took care of us. I wish she could be my guide on every trip I take. I really like staying in Sliema for two nights and then two nights in Valletta to get two different perspectives of the city. The hotel in Gozo was delightful. I am telling everyone I know to go to Malta and get Charmaine as their tour guide"

Trip dates & details
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Sorrento, Amalfi Coast and Capri Private Tour
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5/5 Excellent
51 reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Visit the impressive excavation of Pompeii
  • Enjoy a full day tour of Capri Island
  • Discover the picturesque Amalfi Coast and Positano
  • Taste the traditional Neapolitan Pizza
  • Visit Naples and its old town

Themes

Cultural, Culinary & Wine

What travelers are saying

"Both the Sicily tour and the week in Malta were wonderful. The tour guide in Sicily who took us around Palermo and to Monreal was very knowledgeable, especially in the Cathedral.The guide who took us through the Greek temples was also super interesting and personable. The driver, Francesco, who took us to the Roman house spoke very good English and took time to point out a lot of things we would have missed otherwise. All of the hotels in Sicily were nice but the one in Agrigento was really special.I am glad we skipped the wine tasting the day of Mt. Etna and Taormina because we wouldn't have been able to see much of Taomina otherwise. Sicily is so big you can't see everything in a week but I think your tour does a great job of hitting the highlights. It was great. The tour in Malta was even better. Malta is a fascinating place but what made it really great was having Charmaine as our tour guide. She did a really exceptional job of explaining and showing her country to us. She is knowledgeable, enthusiastic and fun to be with. She really took care of us. I wish she could be my guide on every trip I take. I really like staying in Sliema for two nights and then two nights in Valletta to get two different perspectives of the city. The hotel in Gozo was delightful. I am telling everyone I know to go to Malta and get Charmaine as their tour guide"

Trip dates & details
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Health Safety

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Highlights of Sicily Private 8 Days Tour from Catania
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5/5 Excellent
51 reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Visit the charming town of Taormina
  • Explore the Valley of Temples of Agrigento
  • Admire Mt. Etna, the highest volcano in Europe
  • Discover the picturesque Siracusa and Ortigia
  • Try the authentic Sicilian food and local wines

Themes

Cultural, Culinary & Wine

What travelers are saying

"Both the Sicily tour and the week in Malta were wonderful. The tour guide in Sicily who took us around Palermo and to Monreal was very knowledgeable, especially in the Cathedral.The guide who took us through the Greek temples was also super interesting and personable. The driver, Francesco, who took us to the Roman house spoke very good English and took time to point out a lot of things we would have missed otherwise. All of the hotels in Sicily were nice but the one in Agrigento was really special.I am glad we skipped the wine tasting the day of Mt. Etna and Taormina because we wouldn't have been able to see much of Taomina otherwise. Sicily is so big you can't see everything in a week but I think your tour does a great job of hitting the highlights. It was great. The tour in Malta was even better. Malta is a fascinating place but what made it really great was having Charmaine as our tour guide. She did a really exceptional job of explaining and showing her country to us. She is knowledgeable, enthusiastic and fun to be with. She really took care of us. I wish she could be my guide on every trip I take. I really like staying in Sliema for two nights and then two nights in Valletta to get two different perspectives of the city. The hotel in Gozo was delightful. I am telling everyone I know to go to Malta and get Charmaine as their tour guide"

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

Health Safety

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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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