Just 16 miles long and three miles wide, the Caribbean island of Anguilla packs a serious punch. The northernmost Leeward Island features 33 stunning beaches (two for every mile), lively neighborhoods and cozy beach bars to watch the sun set.
There’s only one true way to get up close and personal with all Anguilla has to offer – hop on a bike.
Anguilla’s roads can be swerving and narrow, so a guide is highly recommended for your first time around the island. The road quality is good, but look out for the occasional pothole. There are also no designated bike paths.
The east side of the island is much less populated and trafficked. So other than the occasional goat looking for munchies outside its homestead, you won’t encounter quite the number of obstacles or congestion as on the more developed westside areas.
In the northeast, you’ll find higher road elevations and the stunning Shoal Bay East – a nearly two-mile stretch of white stand accented by sea grape and coconut trees. This beach is a great spot to park your bike, sip a cocktail or stop for lunch.
Over the past three years, Shoal Bay East has experienced a burst of luxury hotel activity. Leading the way are ultra-contemporary Zemi Beach House and the truly luxe Manoah Boutique Hotel. Beach-bar lovers can groove to the island feel at Uncle Ernie’s or Tropical Sunset.
By comparison, the west side of the island is where bikers will find paved roadways, along with the bulk of the island’s retail establishments and oceanfront hotels. Expect about 90% of these roads to provide a smooth ride.
The nearly two-mile long Rendezvous Beach offers a handful of bike entrance points, breathtaking views and glimpses into Anguilla’s hospitality history. On the east end of town, you’ll find Rendezvous Bay Hotel. The boutique hotel dates from 1962, when it opened with just five rooms. The resort now boasts 44 rooms, including four beachfront villas.
Pedal further west of town and you’ll discover one of Anguilla’s most luxurious hotels – CuisinArt Golf Resort and Spa, The Reef Resort and CuisinArt Golf Club. These Anguillian hospitality landmarks are positioned on a perfect strip of sand that delivers awesome views of the neighboring island of St-Martin.
Beach-bar lovers will find Rendezvous’ best beach access at the Dune Preserve sign. Bike on a somewhat bumpy road until you see an open parking area. Hop off and turn right on the beach for a cold one at the Sunshine Shack or the Dune Preserve, where in the evenings you’ll often hear music courtesy of owner Bankie Banx or his son Omari.
Over the past decade, Meads Bay Beach has gained a reputation beyond breathtaking views. The northwest locale has slowly become known as a foodie paradise.
Bikers can access the area via the paved road entrances leading to several hotels and restaurants hugging the beach. By day, Straw Hat restaurant and Blanchard’s Beach Shack are always hopping with a menu filled with fresh food.
Expect easy beach walking on fine white sand and plenty of gawking opportunities at the yachts frequenting Meads Bay. If you're lucky, you might catch the show that local dolphins occasionally put on for the lunch crowd.
One mile north of Meads Bay is a decadent expanse of beach called Barnes Bay. Feel your feet sink into the softest sand you’ve ever experienced. The best place to access Barnes Bay is at the sign marking the former Oliver’s Restaurant. Cruise down a paved road to the base of a hill, then park your bike and explore this mile-long secluded beach. Another access option is the paved entrance to Mango’s Seaside Grill restaurant.
Barnes Bay is a haven for mega-villas, and it’s also home to the Four Seasons Resort’s Half Shell Beach Bar. It’s at least 50-50 that your only companion on Barnes Bay Beach will be solitude. A beachside rock formation resembling a giant iguana is a great photo opportunity. Barnes Bay’s western exposure also makes the beach a great vantage point for sunsets.
Curling under Anguilla’s southern tip is Maundays Bay, a glorious beach consisting of two crescent-shaped coves. This beach is home to Belmond Cap Juluca Resort, a long-time luxury resort that is a favorite of the rich and famous.
A stone’s throw from Maundays Bay is Sheriva Boutique Villa Hotel. The bridge crossing from Sheriva’s salt pond is the best option for accessing Maundays Bay Beach by bike. The salt frothing from the ground resembles a bubble bath.
Beaches aren’t the only destination to head to in Anguilla – there's always art too. The Devonish Art Gallery, located less than a mile northwest from Maundays Beach, houses a collection of handcrafted wood carving, stone sculptures, beaded jewelry and antique maps.
One of Anguilla’s main bicycle ambassadors is car rental entrepreneur Ronnie Bryan. Bryans Car Rentals is among a handful of places in the country for professional road bicycle rentals. The former Commonwealth Games racer offers Trek, Origin8 and Giant bikes for $25 per day.
Early morning group rides are available for intermediate and elite-level cyclists. Bikes, along with pedals, helmets and seats can be delivered directly to your hotel.
Group riding options are available with routes ranging between 15 and 25 miles. One popular route begins in Anguilla’s fashionable West End and arches toward Sandy Ground, a crowd favorite that features plenty of beach bars and restaurants.
For those staying near the white-sand beaches of Shoal Bay East on Anguilla’s northwest end, Bryan offers a back-roads route toward the airport, North Hill and the Sandy Ground roundabout. The route also includes a cliffside perch with dramatic views of the island.
Other bike-rental outlets include Anchor Miniature Golf and Boo’s Cars & Cycle Rentals. Cost of a rental ranges between $20 and $25 USD per day. For something with a little more horsepower, Freedom Rentals rents ATV quad bikes.
If you go
The annual John T. Memorial Cycling Race is held in July and honors the memory of Anguilla cycling pioneer John Thomas. The race is held in The Valley with last year’s event drawing 90 participants. The elite category race is 80 miles and it’s 65 miles for juniors.