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 (45 - 62 shown)

The Best of Italy
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5/5 Excellent
100+ reviews
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Private guided tour of Venice
  • Opportunity to boat tour on the Grand Canal
  • Private guided tour of Florence
  • Private tour of Chianti wine region with tasting and lunch
  • Explore private guided tour of Pisa
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Themes

Cultural, Culinary & Wine

What travelers are saying

"We were very happy with the trip and how we worked together with you to plan everything. All of the places we went were amazing. Rome had amazing ancient history, art, and architecture as did Pompeii, and Florence had amazing Renaissance history, art, and architecture, while Milan had a little of both but also with the feel of a modern city. The Amalfi Coast and Lake Como were beautiful. We loved Positano (where we stayed) and Ravello best of the places of the places we visited in The Amalfi Coast because they had the most charm and beauty and the least people. In Lake Como, we stayed in Bellagio, but everyplace we visited in Lake Como was beautiful and charming. However, Bellagio, drinking wine and watching the sunset in Varenna, and the boat tour of the lake stood out as our favorite activities. The food was also amazing everywhere, from local places to fine dining the food was fantastic and memorable. We loved Italy. It’s beautiful, and we’ll definitely come back. All of the travel arrangements were excellent and everything was easy. The drivers were friendly and spoke good to excellent English as well as Italian. And having the extra phone was a nice convenience. We didn’t have any stress or difficulties during the trip about the details as they were all taken care of with excellent results. Our favorite drivers: Naples to Positano and back (and Pompeii) Salvatore was excellent. Driving with him was like being with a friend or family member. He was very concerned with our comfort and always suggested places to stop for pictures or a view and had great knowledge of the Naples and The Amalfi Coast. He was also a gentle driver and never made us uncomfortable. Florence Day Trip – I apologize but his name escapes me (maybe Giorgio?), but he was excellent for all the same reasons we liked Salvatore. He even took us to his favorite Gelato shop near his home town and it was so much better than most of what we tried, and since he grew up there he had lots of really interesting local history Milan to Bellagio – I apologize I also forgot this gentleman’s name, but he was a good driver especially around all the curves to and from Bellagio. Not as talkative as the other two, but very friendly and a gentle driver Our favorite guides: Vatican / Franchesca – Interesting personality and very different that the usual guide experience, but we enjoyed her character. She did what we were interested in doing and never let anyone forget that we (and she) were VIP! Pompeii – I apologize I forget her name, but she was very nice and attentive and very interested in what we wanted to know and see and learn more about. It felt tailored to us and what we wanted, which is why you hire a private guide! All of the other guides and drivers were good but the ones above were the best and most memorable. Thanks again for the great trip! We would definitely recommend you to friends, and in fact we already did recommend our friends Derrick and Lorena to you."

Trip dates & details
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Rome and Sorrento Vacation for Seniors
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Relive ancient Rome history
  • Explore the Vatican treasures
  • Visit the remnants of Pompeii
  • Discover the magnificent Amalfi Coast
  • Experience an unforgettable day in Capri
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Themes

Cultural, 50 Plus

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

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Highlights of Italy Family Vacation
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Discover the magical city of Venice by land & water
  • Become a detective through a family scavenger hunt in Venice
  • Create your very own Venetian mask
  • Experience the art of glass blowing and lacemaking
  • Discover Florence & face to face with Michelangelo’s David
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Themes

Cultural, Family Friendly

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

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Rome to Venice Italy Tour for Seniors
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Discover the splendors of Rome
  • Immerse yourself in ancient Roman times
  • Admire the Vatican treasures
  • Enjoy the walled hilltop town of Orvieto
  • Journey to the Renaissance & meet Michelangelo’s David
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Themes

Cultural, 50 Plus

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

Trip dates & details
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Best of Sicily in 10 Days Tour from Palermo to Taormina and Siracusa
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Discover the Royal Palace and the glittering Norman mosaics in the Palatine Chapel Marvel at the stunning collection of 12th-century mosaics at the Duomo di Monreale
  • Stroll the cobblestone streets of Erice, a beautiful Phoenician and Hellenistic town
  • Delve into the legendary Greek temples of Segesta
  • Explore the charming medieval town of Cefalù
  • Venture to Mt. Etna, the world’s largest active volcano
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Themes

Cultural, Family Friendly

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

Trip dates & details
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Venice to Rome Classic Italy Family Trip
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Experience the magical city of Venice by land & water
  • Cruise to Venice neighborhood island of Murano
  • Uncover Florence’s Renaissance past
  • See Renaissance art shaped in the towering figure of David at the Accademia
  • Discover the medieval hill towns of Siena & San Gimignano in Tuscany
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Themes

Family Friendly

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

Trip dates & details
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6 Days in Venice Family Vacation
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Discover Venetian myths & legends
  • Experience the secrets of Venice through a all-ages scavenger hunt
  • Create your own Venetian mask under the guidance of a master mask maker
  • Delve into the ancient history of St. Mark’s Basilica
  • Explore the intrigues of the Doge Palace
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Themes

Cultural, Family Friendly

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

Trip dates & details
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From Naples to Puglia: 10 Days Southern Italy Family Trip with Kids
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By Nancy Aiello 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
100+ reviews
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Explore the vibrant city of Naples & make pizza from scratch
  • Enjoy the scenic Amalfi Coast
  • Discover the ruins of Pompeii
  • Visit the Unesco World Heritage Sites of Matera & Alberobello
  • Taste the beauties and flavors of Bari
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Themes

Cultural, Family Friendly

What travelers are saying

"Awesome!!! We absolutely loved our tour of ancient Rome. Our guide was fun, extremely knowledgeable and passionate about his subject. This experience was highlight of our stay in Rome. My only regret is that we left in a bit of a hurry - my husband's luggage was lost, he was wearing same clothes from travel & uncomfortably hot & anxious to replenish wardrobe - thus, I neglected to tip our guide. I feel terrible as he was so good with our family & kids have been talking about what they learned. If we had more time in the city, I would have arranged for another guided tour of St. Peter's. Please excuse tardy review, my internet connection has not been dependable during the trip. We return to Rome tomorrow for a night before returning to Chicago with wonderful memories. Best regards, Kathleen M. – Chicago, USA"

Trip dates & details
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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...

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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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