Top Italy Luxury Homestays & Cultural Immersion Trips & Packages 2025/2026

Our 98 most popular Italy Luxury Homestays & Cultural Immersion Trips & Packages trips. Compare tour itineraries from 17 tour companies. 29 reviews.

98 Trips match your criteria (1 - 22 shown)

Country Roads of Italy (Summer, Small Groups)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

  • Rome: Discover ancient treasures of Rome with a passionate local. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
  • Castel Gandolfo: Explore the artistic treasure of the Villa Barberini Gardens and marvel at the intricately designed mosaic flower beds and fountains.
  • Sorrento: Perched upon the cliffs, lookout to see the mighty Mount Vesuvius across the Bay of Naples.
  • Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
  • Capri: Explore Capri town with your Local Expert and see the whitewashed houses, winding alleyways, small cafes, fashionable boutiques and artisans studios.
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Themes

Cultural

What travelers are saying

"Got good overview of what history of sites seen."

Trip dates & details
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Country Roads of Southern Italy and Sicily (Summer, Classic)
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4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

  • Rome: Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place, around ancient treasures like the Trevi Fountain, the Pantheon and Piazza Navona.
  • Sorrento: Perched upon the cliffs, lookout to see the mighty Mount Vesuvius across the Bay of Naples.
  • Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
  • Pompeii: Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the first century.
  • Alberobello: Led by a Local Expert, explore this UNESCO World Heritage Site showcasing the Trulli of Alberobello. Circular structures with conical roofs that are domed within, built from local limestone and stacked without using mortar.
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Themes

Cultural

What travelers are saying

"Got good overview of what history of sites seen."

Trip dates & details
Save this trip to your favorites or other list
More
Country Roads of Italy (Summer, Classic)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

  • Rome: Discover ancient treasures of Rome with a passionate local. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
  • Castel Gandolfo: Explore the artistic treasure of the Villa Barberini Gardens and marvel at the intricately designed mosaic flower beds and fountains.
  • Sorrento: Perched upon the cliffs, lookout to see the mighty Mount Vesuvius across the Bay of Naples.
  • Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
  • Capri: Explore Capri town with your Local Expert and see the whitewashed houses, winding alleyways, small cafes, fashionable boutiques and artisans studios.
Show more

Themes

Cultural

What travelers are saying

"Got good overview of what history of sites seen."

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

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
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Country Roads of Umbria & Tuscany (Summer, Small Groups)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

  • Assisi: See St. Mary of the Angels Church and join your Local Expert to walk through the cobbled streets and beautifully preserved medieval laneways of this quaint town.
  • Assisi: With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
  • San Gimignano: Visit the Tuscan town of San Gimignano, often called the 'Medieval Manhattan' of Italy.
  • Florence: Join a Local Expert to view the multi-colored marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square. See the area around Santa Croce Basilica, famous for the quality of its luxury goods.
  • Rome: Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica’s simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
Show more

Themes

Cultural

What travelers are saying

"Got good overview of what history of sites seen."

Trip dates & details
Save this trip to your favorites or other list
More
Italian Elegance (Summer, Classic)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

  • Rome: Discover ancient treasures of Rome with a passionate local. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
  • Florence: Enjoy a stroll through Renaissance Florence and admire the medieval buildings that gave birth to this new style of architecture.
  • San Gimignano: Visit the Tuscan town of San Gimignano, often called the 'Medieval Manhattan' of Italy.
  • Pisa: During your orientation, your Travel Director will show you the baptistery bristling with marble spines, and the colonnaded bell tower lurching behind the 11th-century cathedral - the famous Leaning Tower of Pisa.
  • Portofino: Cruise from Santa Margherita and get a taste of the sweet life in this elegant resort.
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Themes

Cultural

What travelers are saying

"Got good overview of what history of sites seen."

Trip dates & details
Save this trip to your favorites or other list
More
Easy Pace Italy (Summer, Small Groups)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Rome: Discover ancient treasures of Rome with a passionate local. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
  • Florence: Enjoy a stroll through Renaissance Florence and admire the medieval buildings that gave birth to this new style of architecture.
  • Pisa: Your Local Expert will show you the baptistery bristling with marble spines, and the colonnaded bell tower lurching behind the 11th-century cathedral - the famous Leaning Tower in the Square of Miracles.
  • Venice: With your Travel Director cruise to St. Mark's Square and see the Doge's Palace, Bridge of Sighs and St. Mark's Basilica.
  • Venice: Delight in the magic of this charming city as you glide along the canals by gondola.
Show more

Themes

Cultural, 50 Plus, Local Immersion & Homestays

What travelers are saying

"Got good overview of what history of sites seen."

Trip dates & details
Save this trip to your favorites or other list
More
Country Roads of Umbria & Tuscany (Summer, Classic)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Trip pace
Balanced schedule

Highlights

  • Assisi: See St. Mary of the Angels Church and join your Local Expert to walk through the cobbled streets and beautifully preserved medieval laneways of this quaint town.
  • Assisi: With a Local Expert, find out why the Basilica of St. Francis is considered one of the crowning achievements of Europe.
  • San Gimignano: Visit the Tuscan town of San Gimignano, often called the 'Medieval Manhattan' of Italy.
  • Florence: Join a Local Expert to view the multi-colored marble cathedral, bell tower and baptistery, adorned by Ghiberti's Gates of Paradise. Visit the political heart of the city, Signoria Square. See the area around Santa Croce Basilica, famous for the quality of its luxury goods.
  • Rome: Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica’s simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
Show more

Themes

Cultural

What travelers are saying

"Got good overview of what history of sites seen."

Trip dates & details
Save this trip to your favorites or other list
More
Easy Pace Italy (Summer, Classic)
Save this trip to your favorites or other list
4.6/5 Excellent
100+ reviews
Group Tour
Why we love them
They really care about everyone's individual needs on each tour and they have an incredible attention to detail.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Rome: Discover ancient treasures of Rome with a passionate local. See Circus Maximus and the Ancient Forum, where Ancient Roman political life and law courts mingled with open-air markets and shops.
  • Florence: Enjoy a stroll through Renaissance Florence and admire the medieval buildings that gave birth to this new style of architecture.
  • Pisa: Your Local Expert will show you the baptistery bristling with marble spines, and the colonnaded bell tower lurching behind the 11th-century cathedral - the famous Leaning Tower in the Square of Miracles.
  • Venice: With your Travel Director cruise to St. Mark's Square and see the Doge's Palace, Bridge of Sighs and St. Mark's Basilica.
  • Venice: Delight in the magic of this charming city as you glide along the canals by gondola.
Show more

Themes

Cultural, 50 Plus, Local Immersion & Homestays

What travelers are saying

"Got good overview of what history of sites seen."

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

Italy Luxury Homestays & Cultural Immersion Trips & Packages Reviews

A

Amy D.

Dec 2024

Written on

everything was amazing.

We will never travel without Charlie and his crew. It...

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...

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...

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...

C

Caroline Ufford

Feb 2023

Written on

I highly recommend booking with Charlie and this tour.

I highly recommend booking with Charlie and this tour. Sicily is a beautiful place. This trip allows you to explore its towns will being well accompanied by trustwor...

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