North America Luxury Cycling Trips & Packages Tours & Trips

50 North America Luxury Cycling Trips & Packages trips. Tours from 16 tour companies. 72 reviews.

50 Trips match your criteria (21 - 40 shown)

Maryland: Eastern Shore & Chesapeake Bay
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Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Sail the eastern shores with Captain Ed aboard the skipjack HM Krentz
  • Feast on the region’s famous seafood
  • Ride through the Blackwater National Wildlife Refuge, a haven for more than 250 bird species, and learn about Harriet Tubman at the newly opened Underground Railroad State Park and Visitor Center
  • Travel on the country’s oldest privately owned ferry (since 1760), across the Tred-Avon River between Oxford and Bellevue
  • Cycle the quiet country roads leading to the charming small towns of Oxford, St. Michaels, Rock Hall, and Easton

Themes

Nature & Wildlife, Cycling & Biking, Birding, Photography

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."

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South Carolina & Georgia: Charleston to Savannah
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Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Cycle by the pastel-hued houses of Charleston, marveling at views of sailboats and historic Fort Sumter.
  • Immerse yourself in the legacy of the Gullah people when you visit the Sea Island of St. Helena and the culture-rich Penn Center.
  • Step back in time with a cycle through the famed Bonaventure Cemetery and a guided walking tour of the charming streets of Savannah.
  • Ride beneath a magnificent avenue flanked by live oaks as you approach the historic Wormsloe Plantation.
  • Cycle beneath the live oaks of the Spanish Moss Trail to arrive among the antebellum architecture of Beaufort.

Themes

Cultural, 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
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Vermont: Lake Champlain Islands, Burlington & Stowe
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Group Tour
Lodging level
Premium - 4 star
Physical level
Extreme
Trip pace
Full schedule

Highlights

  • Enjoy deluxe accommodations: a boutique hotel, a cozy Vermont inn, and a luxurious mountain resort
  • Enjoy a scenic ride on South Hero Island with views of the Green Mountains and the Adirondacks
  • Visit a local vineyard for a picnic lunch and wine-tasting
  • Tour the Shelburne Museum, an extraordinary collection of 150,000 works
  • Ride through the heart of Stowe on a dedicated path

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
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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
Maine: Acadia National Park
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Group Tour
Lodging level
Premium - 4 star
Physical level
Extreme
Trip pace
Full schedule

Highlights

  • Ride along Rockefeller’s historic and car-free carriage roads through Acadia National Park
  • Practice your lobster-cracking skills at a traditional bake at the Bar Harbor Inn
  • Pause at Jordan Pond’s pristine waters reflecting the beautiful curves of the Bubbles
  • Ride through a refreshing and unspoiled landscape of rugged coastline, forested coves, and idyllic fishing harbors

Themes

Cultural, 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
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Arizona: Saguaro National Park & the Sonoran Desert
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Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Explore the walking trails and fascinating exhibits of the highly regarded Arizona Sonora Desert Museum.
  • Bike and picnic among the beautiful saguaro cacti of Saguaro National Park.
  • Visit the Tumacácori National Historical Park for a self-guided tour, home to three Spanish mission communities and beautiful orchards and gardens.
  • Cycle on The Loop, named the number one bike path in America by USA Today, through vibrant Tucson, along the Santa Cruz and the Rillito Rivers.
  • Savor local cuisine infused with Native American, Spanish, Mexican, and Anglo-American influences.

Themes

Cultural, Nature & Wildlife, Cycling & Biking, Birding

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
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Mississippi: The Natchez Trace
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Group Tour
Lodging level
Premium - 4 star
Physical level
Extreme
Trip pace
Full schedule

Highlights

  • Roll through centuries of history along the Natchez Trace Parkway, a National Scenic Byway and All-American Road.
  • Ponder the legacy of the Civil War at the ruins of the Windsor Plantation.
  • Relive the Siege of Vicksburg on a guided tour with a local historian as you tour Vicksburg National Military Park by bicycle.
  • Visit the sprawling Emerald Mound, one of the largest Native American ceremonial sites.
  • Customize your own “Pilgrimage” of Natchez’s stately antebellum homes.

Themes

Cultural, 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
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Georgia & Florida: Jekyll Island & St. Augustine
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Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Cycle past the sprawling beaches, grand “cottages,” and historic ruins of Jekyll Island.
  • Navigate your kayak through a salt marsh preserve in search of eagles, otters, and dolphins.
  • Visit the scene-stealing St. Augustine Lighthouse and the nearby pristine four-mile beach of Anastasia State Park.
  • Embark on a sunset cruise on the Schooner Freedom, a fine testament to Civil War blockade runners.
  • Cycle the farmlands of St. John’s County, pedaling past potato and cabbage fields, small farming communities, and the tranquil St. John’s River.

Themes

Cultural, Nature & Wildlife, Cycling & Biking, Rafting, Kayaking, Canoeing

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
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Colorado: Aspen to Vail, Valleys of the Rockies
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Group Tour
Lodging level
Premium - 4 star
Physical level
Strenuous
Trip pace
Full schedule

Highlights

  • Ride among alpine peaks and breathe bracingly clean air as you discover the majestic beauty of the Colorado Rockies
  • Enjoy easy, hand-selected routes that take advantage of descending canyons, valley floors, recreational trails, and paved bike paths
  • Marvel at the breathtaking views of “The Bells,” twin 14,000-foot summits mirrored in sublime reflection at Maroon Lake
  • Cycle the gradual descent through the Roaring Fork Valley on the car-free Rio Grande Trail from Aspen to Glenwood Springs
  • Learn about early settlers and the history of the 19th-century Colorado Silver Boom during an interpretive walk through a deserted mining town

Themes

Nature & Wildlife, Cycling & Biking, Photography

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
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North America 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...

A

Antonia

Oct 2024

Written on

Western USA National Parks Explorer

This was one of the most amazing trips I have done to date, and I have travelled far. It was simply extraordinarily beautiful. The group size perfect, and the guide ...

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