Top Italy Hiking Custom Private Tours & Packages In 2025/2026

Our 35 most popular Italy Hiking Custom Private Tours & Packages trips. Compare tour itineraries from 10 tour companies. 20 reviews.

35 Trips match your criteria (1 - 22 shown)

Italy (Sicily): See & Experience it ALL in 7 Days, 1st Class Custom Tours
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By Charlie The Traveler
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
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!"

Trip dates & details
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Italy's Active Adventures: From Rome to Venice
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Conquer the rugged trails of the Dolomites and the scenic routes along the Amalfi Coast.
  • Cycle through the rolling hills of Tuscany, experiencing its world-renowned landscapes.
  • Challenge yourself with rock climbing adventures on the cliffs of the Amalfi Coast and the Dolomites.
  • Immerse in the natural beauty of Lake Garda with extensive trekking and cycling activities.
  • Explore the historic streets of Rome and the romantic canals of Venice as bookends to your adventure.

Themes

High Adventure, Outdoorsy

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Italian Adventure: Rome to Venice
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Discover the historic wonders of Rome, including the majestic Colosseum.
  • Cycle through the rolling hills and vineyards surrounding Florence.
  • Capture the unique beauty of Venice's canals through your lens.
  • Hike the scenic paths offering panoramic views of Italy's stunning landscapes.
  • Experience the rich culture and vibrant street life of Italy's famous cities.

Themes

Cultural, Education / Learning, High Adventure

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Italy's Natural Splendors: A Premium 12-Day Journey
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Embark on guided hikes through Italy's majestic national parks, including Gran Paradiso and Stelvio
  • Capture the beauty of Italy's diverse flora and fauna through dedicated photography sessions
  • Experience the unique ecosystems of Val Grande and the picturesque trails of Cinque Terre
  • Enjoy bird watching excursions, spotting rare and endemic species in their natural habitats
  • Conclude your journey with relaxing days in Venice, exploring its tranquil canals and rich history

Themes

Nature, Eco, Sustainable & Green Travel

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Wild Italy: Camping Adventure
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Camp under the stars in Italy's most scenic spots
  • Hike through the rugged beauty of the Dolomites
  • Explore the rolling hills and vineyards of Tuscany
  • Discover Rome's ancient wonders and vibrant culture
  • Unwind in the serene settings of Florence's countryside

Themes

High Adventure, Outdoor Sports

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Italy's Active Outdoors Adventure
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Cycle through the stylish streets of Milan and along the stunning shores of Lake Como.
  • Trek the rugged trails of the Dolomites, experiencing panoramic views and pristine nature.
  • Mountain bike through the scenic landscapes of Tuscany, enjoying the region's famous vineyards and olive groves.
  • Explore the dramatic cliffs and coastal paths of the Amalfi Coast on foot and by bike.
  • Conclude your journey with a mix of ancient history and modern culture in Rome.

Themes

High Adventure, Outdoorsy

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Italy's Active Outdoors Adventure
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Cycle through the stylish streets of Milan and along the stunning shores of Lake Como.
  • Trek the rugged trails of the Dolomites, experiencing panoramic views and pristine nature.
  • Mountain bike through the scenic landscapes of Tuscany, enjoying the region's famous vineyards and olive groves.
  • Explore the dramatic cliffs and coastal paths of the Amalfi Coast on foot and by bike.
  • Conclude your journey with a mix of ancient history and modern culture in Rome.

Themes

High Adventure, Outdoorsy

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Hidden Gems of Italy
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By TripRover
ai_enhanced
5/5 Excellent
5 reviews
Private Guided
Why we love them
TripRover AI turns travel into a tailor-made journey, mapping your interests to the world.
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Capture the stunning vistas of the Amalfi Coast and its rugged trails.
  • Explore the ancient sassi of Matera and the iconic trulli houses in Alberobello.
  • Delve into the rich history and mosaic art of Ravenna.
  • Enjoy authentic Italian cuisine and vibrant local culture in Bologna.

Themes

Cultural Immersion And History, Unique Experiences

What travelers are saying

"The overall experience was very good. The trip was designed perfectly as per my expectations."

Trip dates & details
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Italy Hiking Custom Private Tours & Packages Reviews

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...

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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