5 Unthinkable Cycling Holidays for the Adventurous Cyclist

Two cyclists riding in Glacier National Park with mountains, trees, and a river nearby on a cycling holiday

At a time when supply chain shortages and uncomfortably high prices get all the attention, cycling holidays remind us of what matters most in this world—unfathomable riding destinations across the globe. Whether you’re planning for this year’s trip or brainstorming for another year, these five bike travel opportunities far surpass 90% of all living bucket lists. 

Escape Adventures Announces Santa Cruz Mountain Biking Adventure

Santa Cruz’s identity ranges from a college town distinctive for its thriving counterculture to Redwoods State Park and barking sea lions. This four-day mountain biking holiday highlights organic farms, the flourishing artisanal beer and wine scene, and long stretches of world-class singletrack. Wilder Ranch State Park, a 700-acre preserve, boasts beautiful trails amongst towering redwood groves. The Fort Ord National Monument offers 86 miles of narrow singletrack trails atop grassland hills and winding trails through oak woodlands and maritime chaparral. Soquel Demonstration State Forest presents long climbs and challenging technical descents. Prices start at $1,899 per person and include about 80-miles of mountain biking. All internal land expenses and services are covered in the cost of the Santa Cruz Mountain Biking tour

“From lush coastal preserves to great spans of giant redwoods, this mountain biking tour is unlike any other offered by Escape Adventures,” said Jared Fisher, Founder, and Director of Escape Adventures.

Wilder Ranch State Park is on the Pacific Ocean just north of Santa Cruz. It was formerly a dairy ranch, and many of the ranch buildings have been restored for use as a museum. From regal structures to beachcombing, big bluffs to inland canyons, riders will explore it all. This is the go-to destination to explore the trails of Santa Cruz County. It offers excellent forested singletrack and gorgeous ocean views of Monterey Bay and the Pacific Ocean.

At the Monterey Bay beachfront, guests will find the immaculately groomed Fort Ord National Monument, a fantastic place to explore by mountain bike, whether you are a beginner or an experienced rider. Dozens of trails wind through the canyons and ridgelines of this open park and a network of gravel roads connecting everything together. The Goat Trail is a favorite – a fantastic descent down one of the higher ridges, and if you are lucky, past the large herd of goats that call the area home.

Soquel Demonstration State Forest (SDSF, colloquially known as Demo), is a favorite destination for Bay Area and Santa Cruz County mountain bikers and contains trails for intermediate and advanced riders, with long climbs and challenging technical descents. The 19-signature trails here total 27-miles, ranging from the advanced Braille DH to six different Flow Trails. 

Your Itinerary:

Day 1-2: Meet in San Jose. Shuttle to the beachside Wilder Ranch State Park, a historic site edging Santa Cruz, California. Cruise the countryside and drink in sea air on the Eucalyptus Bike Loop, through coastal scrubs and open grasslands. After riding the coastal cliffs above the Pacific, shuttle to Fort Ord National Monument (home of the world-famous Sea Otter Classic mountain bike festival). Ride 28-miles of velvety, even-keel singletrack; then its beach-time decompression.

Day 3-4: Shuttle to Soquel Demonstration State Forest. A full day devoted to purpose-built mountain bike trails. The evening unfolds in downtown Santa Cruz.  Our finale takes us to El Corte Madera State Park: a full day of riding splendor amongst giant Redwoods. Shuttle back to San Jose.

Going-to-the-Sun Road with ROAM Beyond

Join ROAM Beyond for an unforgettable weekend of outdoor adventure, farm-to-table feasts, and new experiences with bike-minded friends. Our all-inclusive packages ensure you’ve got everything you need for a perfect weekend.

Every spring, plows return to Glacier National Park’s most treasured byway to begin reopening the road for summer traffic. As they do, a unique opportunity emerges. For a few select weekends, Going-to-the-Sun Road is accessible to cyclists of all ability levels with the option of an e-bike rental. Join ROAM Beyond this year for unforgettable adventures on select weekends in May (26th-29th) and June (2nd-5th, 9th-12th, & 16th-19th).

Your Itinerary:

Thursday: Arrive, check in, and explore ROAM Beyond Glacier’s 20-acre property at the base of the Swan Range. Dinner on your own, with access to our beautiful outdoor cooking spaces.

Friday: Choose between a guided hike or a self-guided mountain bike ride in Flathead National Forest on the Whitefish Trail System. Light breakfast and lunch provided. End the day with a chef-curated farm-to-table feast. 

Saturday: Head into the heart of Glacier riding Going-to-the-Sun Road ride with roundtrip transportation & bike rentals. Shuttles depart at 7:30 AM and 9:30 AM. Light breakfast and lunch provided. Pick-ups in the park depart at 2:30 PM and 4:30 PM. For dinner, a celebration of the ride with gourmet burgers and local brews. 

Rides start from either Apgar Village (experienced riders) or Avalanche Creek Campground (all levels).

Apgar Village to Logan Pass is 32 miles. Avalanche Creek to Logan Pass is 16 miles. 

All riders are picked up at Avalanche Creek Campground. 

Sunday: Rejuvenate before you travel home with a morning yoga session and fresh coffee on-site from Montana Coffee Traders

Hawaii Multi-Sport Adventure: Biking, Surfing, Hiking, and Kayaking

Female cyclist on a road bike in Maui
Maui Cycling Holiday

Referred to by Hawaiians as the “Valley Isle,” the tropical Maui valley connects two of the world’s largest volcanoes into one island cycling paradise. This six-day adventure loops around the valley between Pu’u Kukui to the West and Mt. Haleakalā to the East. In addition to the world-class road biking, surfing lessons and sea kayaking allow guests to broaden their multi-sport experience, while several unforgettable hikes offer a chance to see this beautiful island by foot. Prices start at $3,499 per person double. For more info, visit https://escapeadventures.com/tour/hawaii-maui-multi-sport-road-bike-tour/.

“With over 20 ecosystems and lots of hills, cycling here is always an adventure,” said Jared Fisher, Founder & Director of Escape Adventures. “One minute we’ll be riding through a lush tropical rainforest, and the next we’ll turn the corner onto a huge, sunny lava flow, or drop down onto a private peninsula for some fresh, hot Hawaiian banana bread.”

The people on the island are just as diverse.  Evenings are filled with the sights and scents of real island hospitality as guests are pampered with island feasts, luaus, and hula dancing while staying in private oceanside beach houses.

“We combine extraordinarily scenic cycling with great hiking, sea kayaking, and even surfing, to pack the best Maui has to offer into an active, yet relaxing week-long Hawaiian retreat,” said Fisher.

Day 1: Cycling – West Maui Mountains

Begin the day biking along the coastline of the Mauna Kahālāwai (West Maui Mountains). This western quarter of the island is an eroded volcano that is much older than Mt. Haleakala in the east. Later, climb up 1,000 feet through classic Maui scenery: amazing valleys sprinkled with waterfalls, and majestic sea cliffs line our route.  Next, ride through the old Hawaiian fishing village of Kahakuloa where they still grow Taro.

Day 2: Cycling & Sea Kayaking
Ride past the only winery in Maui along a road with little to no vehicle traffic for almost 40 miles.  This route provides a great introduction to Hawaii with views of the ocean, mountains, and even four of the other Hawaiian islands along the way. There is roughly 3,500 feet of elevation gain over this 30-mile ride.  Shuttle back to Kihei for lunch and to trade out bikes for sea kayaks and an exciting adventure just off the coastline.

Day 3: Surfing & Free Time
Spend the morning learning to surf with a 2-hour private lesson. Head out at the best time of the day to learn, in one of the best places in the world to learn, with expert, personalized instruction. Then head into town for some shopping at the many shops and local markets or relax on one of Kihei’s beautiful public beaches. Those looking for more high-profile sun and sand can head south to the world-famous Big Beach.

Day 4: Hike Mt. Haleakelā    
A trip to Mt. Haleakelā demonstrates the natural history of Hawaii up close. The summit area’s remarkable volcanic landscape quickly gives way to a variety of other ecosystems as one descends down into the park. Pass through as many ecological zones on the drive to the summit as there are between Canada and Mexico. Here, a massive variety of native Hawaiian plants and animals thrive, including some species that exist nowhere else in the world. After taking in the sights from the van, head out on a day hike, exploring one of the park’s many wonders.

Day 5: Cycling Haiku to Ke’anae Village
Cycle through the rainforest to Ke’anae Village.  A tropical atmosphere bursting with lush green foliage, combined with incredible views of both the ocean and Haleakelā, makes this one of the best rides on the planet! In Ke’anae, stop for hot banana bread as waves pound the lava rocks below.  The day’s rides add up to over 3,000 feet of elevation change over more than 50 miles.

Day 6: Hiking – Bamboo Forest
From the trailhead off the famous Hana Highway,  embark on a unique hiking adventure. Venture into a lush section of bamboo forest, passing three classic Hawaiian waterfalls along the route. Bring a swimsuit for a dip in the idyllic freshwater pools that lie at the base of the falls. Cap off the perfect day in paradise with a snack of fresh guava, before concluding the tour after lunch.

***All internal land expenses and services are covered in the cost of this tour. This means from the time Escape Adventures picks you up, all transportation, food preparation, meals, snacks, non-alcoholic beverages, group supplies, and community gear are included. Backcountry permits, licenses, park fees, reservations, and accommodations are also included, along with at least two professionally trained trip leaders, a mobile-first aid and mechanic station, spare bikes, and a support vehicle(s).

NEW “Blue Zone” Chef Tour of Sardinia Unveiled by Tourissimo 

Sardinia Cycling Holiday

Tourissimo and SHS in Sardinia are thrilled to present a new project: a 7-day “Blue Zone” culinary cycling tour of Sardinia hosted by celebrated Chef Mary Sue Milliken. Guests will experience the culinary specialties of both the coast and the mountains and discover the cultural roots of the island while cycling some of its most scenic and traffic-free roads. Chef Milliken will play an important role in helping guests understand and experience the local cuisine and culinary techniques that tell the story of the territory. Lodging includes 4-star hotels. The tour is scheduled for May 29 – June 5, 2022, and prices start at $4,995 per person double (all meals included) and e-bikes are available upon request. For more information, visit https://www.tourissimo.travel/chef-tours/sardinia

“Many travelers describe Sardinia as being a continent unto itself, with each area and town having diverse landscapes and local traditions,” said Tourissimo co-founder Beppe Salerno. “Most of the recipes and dishes are surprisingly different from other areas of Italy, such as filindeu, the ‘thread of god,’ a special pasta considered the rarest in the world.”

Sardinia is one of the very few places in the world that boasts a “Blue Zone ” designation. This refers to areas across the globe where people live longer and have healthier, more natural lifestyles steeped in traditions that have been carried on from generation to generation. Guests will ride straight through this Blue Zone, discovering its unique historical and cultural aspects while indulging in the authentic food and wine along the way.

“We will learn the secrets of longevity on this culinary cycling adventure,” said Tourissimo co-founder Heather Dowd. “In Blue Zones, a large number of inhabitants live to be 100 or older, and their way of life, including the food and wine, is a big part of this longevity.”


  • Experience regional cuisine not found elsewhere in Italy
  • Enjoy a home-cooked lunch in Villasalto hosted by the local traditional keepers
  • Lunch with a shepherd in a unique setting
  • Explore the Village of Oliena and its wine tradition
  • Take in a lecture about Sardinia’s Blue Zone
  • Visit the Bronze Age site of Santa Cristina with its unique water temple  
  • Witness the primordial Gennargentu Mountain Range
  • Tour Orgosolo, the painted village, famous for its murals rich with social commentary
  • Visit Barbagia and Ogliastra, geographical and cultural areas that are the true soul of Sardinia
  • Cycle a fantastic route from Genna Silana Pass
  • Take a day fishing cruise along the Marine Protected Area of Capo Carbonara
  • Bike in the rural inners island and along the Mediterranean coast
  • Visit to the Cittadella dei Musei in the Castello district of Cagliari 

36-Day “Bike Across Europe” Tour

Europe Cycling Holiday

Ride & Seek Adventures, the adventure travel company known for its Hannibal Expedition cycling tour from Barcelona to Rome, is thrilled to announce an even more audacious excursion taking riders on a 36-day, 3,693 km “Bike Across Europe” tour from Paris, France to Tallinn, Estonia. 

The epic adventure crosses eight countries and two continents following in the footsteps of Napoleon’s Grande Armée. It begins in Paris with a spin down the Champs-Élysées, followed by aperitifs under the shadow of the Arc de Triomphe before departing for Germany, Luxembourg, Czech Republic, Poland, Lithuania, Latvia, and Estonia—through rolling vineyards, deep forests, medieval villages, and historic cities. The tour is slated for July 2 – August 6, 2022, and starts at $17,208 USD. There is an option to ride 8-day or 15-day stages of the tour starting at $4,006 USD.

“This is our most epic of epic tours through eight countries as we cycle in the footsteps of Napoleon from Paris to the Russian border,” said Dylan Reynolds, Founder, and Director of Ride & Seek. “It is our very own Ride Across Europe tour that seeks out the road less traveled as we embrace the cultural and culinary highlights along the way.”

Guests will ride across the Champagne region of France into the picturesque, castle-clad green hills of southern Germany. The route then heads through UNESCO-protected medieval villages in Poland to the North Sea. From here, it moves east via the great lakes of Poland and The Baltics. Riders will eventually arrive in Tallinn, Estonia, the country’s cultural hub and capital on the Baltic Sea. 

We will visit expert champagne makers eat wonderful regional cuisine, explore UNESCO recognized sites, and ride through beautiful forests, remote territory, and bustling cities, all in the footsteps of Napoleon.” said Reynolds.

Before you go, consider which of the five Unfathomable Cycling Holidays for the Adventurous Cyclist listed above is atop your bucket list. Will you cross all of Europe on the most expansive bike tour of its kind, or will you journey to the tropical beaches of Maui? Or are you looking forward to the rare sights of Glacier National Park without cars? Regardless of the cycling adventure, you can’t go wrong. The choice is yours! 

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