Island Trails by Bike
A Guided Cycling Trail Tour Through Anguilla’s Hidden Landscapes
Get ready for an adrenaline-fueled ride along the wild, rugged beauty of Anguilla’s more remote areas like Windward Point, Brimigen and the tip of West End! This trail-biking experience isn’t just a workout—it’s a coastal adventure that will leave your heart racing and your senses buzzing. Pedal across red sand and limestone dirt roads, weave through windswept brush, and soak in panoramic views. Feel the thrill as your tires crunch over rocky terrain, with salt spray in the air and seabirds soaring overhead.
Each twist in the trail reveals another breathtaking vista—hidden bays, distant cays, and the untouched side of Anguilla few ever see. Whether you’re a seasoned cyclist or an adventurous beginner, this guided ride takes you through 7 miles of natural wonder.
Or Rent a Quest Bike
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Departure/Return Location
Windward Point (Island Harbour Wharf) | Brimigen (Xtreme Gym, Cedar Village) | West End (Anguilla Art Centre, West End) -
Departure Time
Please arrive by 7:30am -
Return Time
Approximately 10:00am -
Dress Code
Active wear, sneakers -
Included
GuideWater -
Not Included
AccommodationRefreshmentsTransport
From our gallery
Moments from our Cycling Trail Tours
Tour Plan
Cycling Trail Ride - $85/person
- Intensity: Moderate - Difficult
- Included: Trail Bike, Helmet, Gloves and Water
- Minimum: 2 personsSolo bookings are welcome! You’ll either be paired with the nearest available group or may choose to confirm your experience by covering the minimum booking rate for two guests.
- Final confirmation will be provided subsequent to your booking request being sent via the booking calendar.
- A payment link will be sent after final confirmation of your booking request
Tour Location
This experience is available for either of 3 locations: Windward Point, Brimigen or West End
Windward Point
Goat Cave
Tip of West End
Quest Reviews
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Refunds & Cancellations
- 15% (if 72-48 hours before the Experience);
- 30% (if 25-47 hours before the Experience) or
- 100% (less than 24 hours before the Experience).
Matt L.
We had such a great time. The bikes were in perfect condition, the trails were challenging yet fun, the guides were excellent and the views were amazing. We spent a morning away from the relaxing calm of the beaches and took this exhilarating adventure to places on the east end of Anguilla that few tourists ever see. Highly recommended!
Kraemer
We were looking for something to get us out of our beach loungers. This was a homerun for our family of five, active adults. We were concerned about the heat/sun but the constant wind kept us cool as well as the early morning start time. The hybrid bikes were perfect on the mixed riding surfaces. The scenery was spectacular for the entire ride and Clem took us to spots that are hard to find, including a hike to a lighthouse with 360 degree views of the ocean and island! Fun time for all!
Paul M
Anguilla is a magical island. But some of the magic must be found off the beaten path. I did the bike tour to Goat Cave. Wow! This was an incredible experience. Cannot recommend highly enough. Clem is personable, knowledgeable, and well, just fun! One caution though. The trek into the cave involves walking over limestone. My lightweight Sketchers paid the price. Still, well worth it. But wear appropriate footwear. And enjoy the magic of Anguilla. We will return and will do another Quest tour.