Italy Hiking & Walking Custom Private Tours & Packages Tours & Trips

20 Italy Hiking & Walking Custom Private Tours & Packages trips. Tours from 11 tour companies. 23 reviews.

20 Trips match your criteria (1 - 20 shown)

Italy (Sicily): See & Experience it ALL in 7 Days, 1st Class Custom Tours
Save this trip to your favorites or other list
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
Show more

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
Save this trip to your favorites or other list

Health Safety

More
Neaples Epic Trip
Save this trip to your favorites or other list
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 narrow streets of Naples together
  • Enjoy a slice of pizza margherita and a shot of limoncello.
  • Enjoy a pleasant walk through the history and the traditions of Naples
  • Explore the archaeological site that used to be a Roman city

Themes

Nature & Wildlife, Hiking & Walking

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
Save this trip to your favorites or other list
More
Private Tours The Italian Riviera
Save this trip to your favorites or other list
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

  • Lake Como on our way to the Riviera we will stop by Italy’s celebrity lake hangout.
  • Cinque Terre It's no secret these five castal villages connected by a walking track is a must see destination.
  • Lerici ‘The gulf of Poets’, an impossibly pretty bay that inspired the likes of Byon and Shelley who both lived there.
  • Portofino is the glamorous harbor beloved by movie stars and celebrities with good reason.
  • Sanremo The Riviera classic resort town and musical capital of Italy.
Show more

Themes

Nature & Wildlife, Hiking & Walking

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
Save this trip to your favorites or other list
More
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
Naples & the island of Ischia
Save this trip to your favorites or other list
Private Guided
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Discover the original relics from Pompeii on a privately guided tour of Naples Archaeological Museum.
  • Hike the panoramic trails of Ischia and enjoy lunch at a traditional agritourismo.
  • Explore the cosmopolitan city of Naples on a guided walking tour.
  • Relax at Ischia’s thermal baths and beaches.

Themes

Cultural, Nature & Wildlife, Hiking & Walking

What travelers are saying

"Absolutely amazing two week trip to Mexico. Phoebe was very knowledgeable and helped us plan a fabulous itinerary. The hotels she'd recommended were perfect and in excellent locations. Our guides were helpful, friendly and spoke excellent English and when we contacted the Mexico office to squeeze in another excursion, they were responsive and immediately organised everything. All round brilliant customer service and Mexico was the most interesting and beautiful place to visit! Thank you!"

Trip dates & details
Save this trip to your favorites or other list
More
Romantic Italy & Greece
Save this trip to your favorites or other list
Private Guided
Lodging level
Standard - 3 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Watch the sunset over the water from a private catamaran in Santorini.
  • Experience sweeping views of the Amalfi Coast while hiking the Path of the Gods.
  • Sample local wines with views over Santorini’s caldera.
  • Explore the best of Roman culinary traditions on a food-based walking tour of Rome.

Themes

Cultural, Nature & Wildlife, Culinary & Wine, Hiking & Walking

What travelers are saying

"Absolutely amazing two week trip to Mexico. Phoebe was very knowledgeable and helped us plan a fabulous itinerary. The hotels she'd recommended were perfect and in excellent locations. Our guides were helpful, friendly and spoke excellent English and when we contacted the Mexico office to squeeze in another excursion, they were responsive and immediately organised everything. All round brilliant customer service and Mexico was the most interesting and beautiful place to visit! Thank you!"

Trip dates & details
Save this trip to your favorites or other list
More
Paris, Tuscany and Rome
Save this trip to your favorites or other list
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Full schedule

Highlights

  • Visit the intriguing Hospices Museum
  • Explore Swiss Transport Museum, or relax on one of the lovely lakeshore promenades
  • Explore romantic city of Venice
  • Visit a glass-blowing workshop where highly skilled artisans craft anything from delicate figurines to grand chandeliers

Themes

Hiking & Walking, Local Immersion & Homestays

What travelers are saying

"We had a great experience on our WW2 Memorial Tour. The days were well planned and so informative, with a nice balance of informative stops and free time. Our lodging and meals were first rate. Our tour guide was first rate."

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

Unlock Community Benefits

Travel better together

  • Save favorite trips and itineraries
  • Get insider insights
  • Receive personalized recommendations
  • ... and much more
Join community
VIP - The best of Italy from South to North
Save this trip to your favorites or other list
Private Guided
Lodging level
Luxury - 5 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Agrigento and the Greek Temples Valley
  • Treasures and food in Palermo tour
  • Taormina private walking tour
  • Mount Etna with wine tasting
  • Lecce highlights with food and wine tasting
Show more

Themes

Cultural, Culinary & Wine, Hiking & Walking, Photography, Trekking & Expeditions

What travelers are saying

"My wife of 31years and I wanted to start our retirement with a bang, and top travel delivered. Private guides with easy entry into all the major attractions, made our vacation special. Top travel tailored our trip to our interests. You do pay a premium, but it was worth it."

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

Health Safety

More
Your Rome City Break
Save this trip to your favorites or other list
Private Guided
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Balanced schedule

Highlights

  • Colosseum and Roman Empire walking
  • Vatican and Sistine Chapel private walking tour

Themes

Cultural, Hiking & Walking, Photography

What travelers are saying

"My wife of 31years and I wanted to start our retirement with a bang, and top travel delivered. Private guides with easy entry into all the major attractions, made our vacation special. Top travel tailored our trip to our interests. You do pay a premium, but it was worth it."

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

Health Safety

More
Travelstride Gift Card
One card, thousands of extraordinary trips
Gifts Card

Best Italy Hiking & Walking Custom Private Tours & Packages Tours by Duration

Italy Hiking & Walking 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...

Write a Review

Always Find the Best

On Travelstride you can find 20 trips to Italy Hiking & Walking Custom Private Tours & Packages and more than 20,000 trips worldwide ranging from budget to luxury and private guided to group tours and everything in between. Only on Stride can you find and compare expert-planned trips from 1,000+ tour operators, cruise lines and local experts. Read traveler and professional reviews so you can confidently find your perfect trip.

Top Tour Companies on Travelstride:
All 1,600+ companies >
Sign in to reveal savings up to $700 per person!