Sometimes we don’t have enough time to see as much of an island as we hope, but one of the best ways to fix that is by renting a bicycle or electric bike. Island tours and professional guides offer travelers roads, trails, and off-the-beaten-paths from which they can explore the Caribbean in ways they haven’t previously imagined.
Serious cyclists can also find new challenges on their favorite islands, as biking legends have designed some of these trails to test the limits of experienced riders. But no matter your skill level, there are myriad bicycle paths and tours in the Caribbean.
The only thing left to do is pack your cycling gear—especially a good helmet.
Tinker’s Trail — St. Lucia
St. Lucia is full of bike trails for riders of all experience levels, and one of the most famous is Tinker’s Trail. Designed by three-time U.S. National Champion and Mountain Bike Hall of Fame inductee Tinker Juarez, this trail was meant to be a “heart thumper” for the most experienced riders, offering a tough uphill run to test a rider’s “conditioning and aerobic capacity.”
But Tinker’s Trail is hardly for everyone, so beginners can hit the easier paths and enjoy a ride at their comfort level while experiencing the beauty and history of St. Lucia.
Cayman Cave Trek — Cayman Island
ECO Rides Cayman offers this four-hour bike tour that takes riders through some of East End’s most scenic areas before arriving at the Crystal Caves. The ride begins near the resort area six miles from the caves, so guests have the chance to see the sights along Queen’s Highway Road. The ride is easy and ECO provides a bike and a helmet.
Guided Bike Tours — Anguilla
What makes Anguilla ideal for cycling is its size. At just 17 miles long and 3 miles wide, the island is easy to navigate and explore, with trails like Katouche and Brimegin providing an intimate, up-close look at the natural beauty. Many resorts—like Zemi Beach House Hotel and Malliouhana—offer guided tours of the island, but it’s just as easy to grab a map and visit everywhere from Sandy Ground to the East End on your own.
Nevis Adventure Tours — Nevis
Nevis’ main road is basically a 20-mile circle, so riding around the entire island is always an option. Nevis Adventure Tours offers more detailed outings that allow riders to learn about the island’s history from their bikes.
The Windwardside Discovery Bike Tour invites riders of all skill levels on a three-hour journey of St. James parish, which boasts the last operating sugar plantation on the island, as well as a haunted estate. For more experienced cyclists, Nevis Adventure Tours offers the Nevis Challenge: Peak of Biking, which covers the entire island, beginning and ending in Newcastle.
Guanica State Forest Trails — Puerto Rico
While Toro Verde is known for its zip-lines, mountain bikers will want to visit the island’s forests and parks for the best trails. The Guanica Biospehere Reserve and State Forest features 12 trails for hikers and bikers, and the park’s guides will help guests determine which are best for their skill levels.
Blue Mountain National Park — Jamaica
There is no shortage of companies and resorts offering bike tours of Blue Mountain National Park, and many of them are perfect for families looking for a casual adventure or even a picnic. Blue Mountain Bicycle Tour offers a straightforward, all-inclusive day ride that is easy on the legs and features plenty of perks, like brunch with real Blue Mountain coffee and a visit to a secluded waterfall. Bikes and gear are also included.
Singletrack Jamaica takes it a step further with custom packages for serious riders who want to spend several days on the trails. This company technically offers rental bikes, but they belong to the employees, so you’d better know what you’re doing out there.
Punta Cana Mountain Bike Tour — Dominican Republic
Outback Adventures in the Dominican Republic provides an eco-friendly mountain bike tour of Punta Cana’s countryside and Macao Beach, and the use of electric bikes makes it perfect for all riders. The tour takes guests on off-road trails and paved roads to share the region’s rich history, while also allowing everyone to stop for shopping and dining. Bikes and gear are included in the rental fees.
Jan Thiel Lagoon — Curaçao
Featuring a trail that was created for the 2006 UCI Mountain Bike World Cup, Curaçao’s Jan Thiel Lagoon is a nature reserve with longer pathways fit for beginner and advanced bikers alike.
WannaBike offers guided tours of the lagoon’s trails, as well as rides through Caracas Bay Peninsula, Koraal Tabak, and Boca St. Michiel/Malpais, which is a great option for more experienced cyclists.
La Desirade Island — Guadeloupe Islands
Like Anguilla, La Desirade‘s small size is what makes it an ideal spot for a bike tour. One main road runs the length of the island, making it so easy for guests to experience everything this small national natural reserve has to offer. Rentals bikes are available on the island, as beaches like Petite-Rivière and Beauséjour await.
Bermuda Railway Trail — Bermuda
While it’s not the Caribbean, this special adventure deserves to be included. Following an abandoned railbed, the Bermuda Railway Trail is a bike trail that runs approximately 18 miles and is split into nine sections, allowing riders to start and end wherever they’d like. The trail offers challenges like bridges and steeper slopes, but it’s also fit for beginners who simply want to see the island’s pink-sand beaches and historic landmarks at a leisurely pace.
