Italy Luxury Cycling Trips & Packages Tours & Trips

49 Italy Luxury Cycling Trips & Packages trips. Tours from 15 tour companies. 396 reviews.

49 Trips match your criteria (21 - 40 shown)

Classic Northern Italy
Save this trip to your favorites or other list
Small Group Tour
Why we love them
They lovingly design their trips, relying on an in-depth understanding of the destinations.
Lodging level
Premium - 4 star
Physical level
Easy
Trip pace
Flexible schedule

Highlights

  • Cycle past the famed architectural attractions of Rome on a guided tour
  • Stay overnight in the Tuscan hills overlooking Siena
  • Enjoy a San Gimignano vineyard tour, wine tasting and cooking class
  • Hike along the cliffs of the Cinque Terre National Park
  • Sip an aperitif on a boat tour of Lake Como
Show more

Themes

Cultural, Nature & Wildlife, Culinary & Wine, Cycling & Biking, Hiking & Walking, Photography, Festivals & Special Events, Relaxing Retreats

What travelers are saying

"A Culture Trip curated trip is a must for anyone burnt out planning their own trips or going to a remote or unfamiliar area. Having a local insider was the highlight of the trip. From the moment we landed to the moment we had to go through security to leave, we were completely taken care of. Our insider gave us great recommendations for restaurants and was very adaptable to any situation that arose."

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

Health Safety

More
Dolomites Bike Tour
Save this trip to your favorites or other list
Small Group Tour
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Uncover the colorful history and culture of Italy and Austria's best-kept alpine secret
  • Tranquil biking amid valleys and storybook villages framed by magnificent limestone peaks
  • Pedal on bike paths past meadows strewn with wildflowers and filled with locals tending the rich soil
  • Wonderful regional wines, including vernatsch, lagrein and gewürztraminer
  • Enjoy a warm welcome at luxurious family-run hotels and savor two Michelin dinners

Themes

Cultural, Family Friendly, Cycling & Biking, Transformative

What travelers are saying

"Until Covid clears, I would steer clear of Backroads. We were partially through their June 2020 Costa Rica tour when a guest tested Covid positive. She and her husband were isolated. The rest of the group were offered wimpy masks. Nobody was offered Covid testing daily and masks were not required of the guests or staff. The guides kept repeating "not in the CDC guidelines." Our group of six decided that the Backroads response was inadequate so returned home mid-excursion. The hotel and food was excellent, but the provided bikes were inadequate. The front derailleurs were poorly adjusted, and most of the riders had the chains come off during the first ride. Hikes or bike rides were conducted in downpours. Disappointed for charging such a premium price."

Trip dates & details
Save this trip to your favorites or other list
More
Italy: Valleys of the Dolomites
Save this trip to your favorites or other list
Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Marvel at the scenic alpine vistas that surround you as you cycle easy bike paths
  • Gain a rare glimpse into the ancient Ladin culture, and feast on mountain specialties
  • Thrill to a 1,900-foot (580-meter) descent along the Val Venosta Bike Path
  • Enter into the dual Austrian-Italian culture of South Tyrol, as you explore the little city of San Candido
  • Explore the beautiful cathedral, cloister, and palace of Bressanone on a guided walking tour

Themes

Nature & Wildlife, Cycling & Biking, Photography, High Adventure

What travelers are saying

"This was the first organized tour my husband and I have ever joined, so we were not sure what to expect , but it turned out to be the best vacation we've ever had. The scenery and food were amazing. We stayed in beautiful hotels. Most of the riding was on paved bike paths so we hardly ever had to deal with car traffic. Our leaders, Andrea and Martin, were funny, informative , and so helpful. We are already planning to go back to Italy with VBT this summer."

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 $200 per person per day
Self-Guided / Independent Tour
Italy: Puglia’s Undiscovered Coast
Save this trip to your favorites or other list
Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Enjoy incomparable accommodations with six nights at luxurious masserie.
  • Share a farm-fresh lunch and taste delicious olive oils with your masseria hosts.
  • Bike from the ancient walled city of Acaya to the beautiful, rugged coast.
  • Enjoy unhurried pedaling along rural pathways heading to the coastal town of Castro Marina.
  • Refresh yourself with a swim in Otranto’s crystalline waters.

Themes

Nature & Wildlife, Cycling & Biking

What travelers are saying

"This was the first organized tour my husband and I have ever joined, so we were not sure what to expect , but it turned out to be the best vacation we've ever had. The scenery and food were amazing. We stayed in beautiful hotels. Most of the riding was on paved bike paths so we hardly ever had to deal with car traffic. Our leaders, Andrea and Martin, were funny, informative , and so helpful. We are already planning to go back to Italy with VBT this summer."

Trip dates & details
Save this trip to your favorites or other list
More
Sicily Magnifica Tour
Save this trip to your favorites or other list
Group Tour
Lodging level
Premium - 4 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Palermo’s amazing Arab-Norman architecture, including 9 buildings recognized by UNESCO
  • Guided visit to Monreale Cathedral
  • Corleone: the rebirth of an iconic mafia village
  • Wine tasting at Planeta Winery
  • Picnic with Poggioreale Antica inhabitants
Show more

Themes

Cultural, Culinary & Wine, Cycling & Biking, Local Immersion & Homestays

What travelers are saying

"Great routes, guides, hotels and bikes!"

Trip dates & details
Save this trip to your favorites or other list
More
Tuscany Biking
Save this trip to your favorites or other list
Small Group Tour
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Enjoy tasting of Tuscan reds
  • Explore vine-covered hills of Chianti
  • Explore Siena
  • Visit a private wine estate for a tasting

Themes

50 Plus, Cycling & Biking

What travelers are saying

"Butterfield and Robinson just planned and executed a great, great trip for us to the Amalfi coast. All the services and hotels were wonderful and the guides were great fun and and well informed. Many nice surprises along the way and an itinerary we would have had trouble putting together on our own was effortless. All guides were well trained the transportation and drivers were polite and on time. The recommended hotels were amazing. We loved every minute of our vacation."

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
Puglia and Matera Magnifica Tour
Save this trip to your favorites or other list
Group Tour
Lodging level
Luxury - 5 star
Physical level
Moderate
Trip pace
Balanced schedule

Highlights

  • Two night stay and a walking tour of Matera where they have just filmed the remake of the colossal Ben Hur movie with Morgan Freeman
  • Captivating clusters of conical trulli structures
  • Discover the white-washed town of Ostuni and the beaches near the fishing village of Savelletri
  • Spectacular fields of ancient olive trees
  • Savory cuisine: grilled vegetables, handmade pasta and fresh seafood!
Show more

Themes

Cultural, Culinary & Wine, Cycling & Biking, Local Immersion & Homestays, Eco, Sustainable & Green Travel, Transformative

What travelers are saying

"Great routes, guides, hotels and bikes!"

Trip dates & details
Save this trip to your favorites or other list
More
Italy: Tuscany, Chianti & Marina di Castagneto
Save this trip to your favorites or other list
Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Indulge in luxurious accommodations where you can relax on a private sandy beach, soak in natural Etruscan hot springs, dine on elegant meals, and more
  • Visit the home of a longtime VBT friend and founder of Cooking in Tuscany, then cook a traditional Tuscan meal with her
  • Learn about different olive oils by taste with the family that owns the Fonte di Foiano olive oil mill as your guide
  • Cycle past Bolgheri’s Super Tuscan vineyards and along its famous cypress-lined avenue, a prelude to the stunning medieval towns of Castagneto Carducci, Sassetta, and Suvereto
  • Explore the fascinating Etruscan city of Populonia, a bustling port in ancient times, and take in breathtaking views of the turquoise waters of Baratti Bay.

Themes

Cultural, Nature & Wildlife, Culinary & Wine, Cycling & Biking

What travelers are saying

"This was the first organized tour my husband and I have ever joined, so we were not sure what to expect , but it turned out to be the best vacation we've ever had. The scenery and food were amazing. We stayed in beautiful hotels. Most of the riding was on paved bike paths so we hardly ever had to deal with car traffic. Our leaders, Andrea and Martin, were funny, informative , and so helpful. We are already planning to go back to Italy with VBT this summer."

Trip dates & details
Save this trip to your favorites or other list
More
Travelstride Gift Card
One card, thousands of extraordinary trips
Gifts Card

Italy Luxury Cycling Trips & Packages Reviews

S

Sarah

Nov 2024

Written on

Western USA National Parks Explorer

This was a fabulous trip with a great tour leader. The last tour of the season turned out to be a very good option; it was pretty cold at times, but we had lots of ...

J

Julie

Oct 2024

Written on

Western USA National Parks Explorer

This was an outstanding trip in every way, with views and sights the rest of the world will struggle to match. The itinerary had to be very full-on in order to achie...

P

Patricia Faust

Oct 2024

Written on

Western USA National Parks Explorer

The last thing I want to do on a tour, is shop for breakfast nearly every day. (We had a lovely breakfast in our hotel only once in 2 weeks). And then there are the...

B

Brian

Oct 2024

Written on

Western USA National Parks Explorer

The tour was excellent, the itinerary well arranged and very interesting, with wonderful scenery. The tour leader (Brianna) was great; as well as being very friendly...

J

John

Oct 2024

Written on

Western USA National Parks Explorer

Top tour. Think your leader, Brianna, faced a few challenges with our mixe...

Write a Review

Always Find the Best

On Travelstride you can find 49 trips to Italy Luxury Cycling Trips & 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!