Guide to Anguilla



Anguilla, the Caribbean’s undiscovered treasure, isn’t just about sprawling on pristine beaches (although there’s plenty of that too!). This island paradise caters to the active traveller as well. Join WAWW Caribbean expert Elena Leo, the Director of Editorial, as she unlocks your unforgettable active Anguilla adventure. From exhilarating boat races to tranquil hikes, playing tennis, or diving into vibrant coral reefs, she will show you how to stay fit and experience the island’s charm, all while soaking up the Caribbean sunshine.


Boat Racing I Anguilla

What is boat racing in Anguilla? Boat racing in Anguilla is the heartbeat of the island. Anguilla’s boat racing scene shatters the typical sports narrative. During boat races, the island’s azure waves are transformed into racetracks where schooners, powered by sheer will and wind, compete not just for titles but for island pride. This spectacle, unique to the island, turns the sea into a stage, where each race is a story of skill, strategy, and community spirit, cheered on by a sea of fans whose allegiance to boats and crews runs as deep as the waters. There’s no spectacle quite like it, with races as vibrant today as they were over a century ago. 

The history of boat racing in Anguilla begins in the early 1900s, against a backdrop of economic hardship. Anguillians, seeking work in the Dominican Republic, would race their schooners home, battling the elements for the glory of being the first back. This competitive spirit sparked a tradition, highlighted in the 1930s by an epic race that saw entire congregations abandon their church service to cheer on the racers from the shore.

Boat racing events in Anguilla today still honour this rich heritage, with boats hand-built using the WEST technique, a testament to the island’s craftsmanship. The racing calendar, peaking from Easter to August, features classes A to C, with Class A drawing the largest crowds. Spectators, or “landracers,” gather along beaches and hilltops, their enthusiasm matched only by the festive atmosphere of barbecues and music.

Anguilla’s boat racing calendar is densely packed with events that stitch the fabric of its maritime heritage into the present. Starting with the Festival del Mar at Easter, this event not only showcases thrilling races but also celebrates with live music, deep-sea fishing contests, and sumptuous local fare. The sailing spectacle continues with the Anguilla Regatta in mid-May, renowned as one of the Caribbean’s premier sailing competitions, known for its challenging courses and robust wind conditions.

As the season sails forward, several key races mark the calendar. The Easter Monday Race in Sandy Ground is a crowd-puller, closely followed by the Anguilla Day Race on May 30th, which also takes place in Sandy Ground, offering another chance to witness the island’s sailing prowess. June brings the Queen’s Day Race at Crocus Bay, a regal nod within the racing lineup. The crescendo of the racing season reaches its peak with the August Monday Race, a spirited competition held on the first Monday in August at Sandy Ground, and the August Thursday Race in Meads Bay.

The season culminates in the Champion of Champions race, a round-the-island marathon for Class A & B boats. Held in August at the close of Boat Racing Week, it’s a grand finale that showcases the best of Anguilla’s boat racing, embodying the island’s deep-seated love for the sea and sailing legacy.

Each event in Anguilla’s boat racing season offers a dash of saltwater, a sprinkle of competition, and a whole lot of island vibe, making it the perfect cocktail for anyone looking to dip their toes into the vibrant culture of Caribbean sailing—no sailing experience is required, just a willingness to embrace the party.

For planners and the spontaneous alike, the Anguilla Tourist Board ( ) is your go-to for a race calendar and everything else you need to know about catching the racing thrill.

Wondering how to join a boat race in Anguilla? It might sound like a thrilling adventure, but it’s not as easy as just showing up and hopping on board. For starters, navigating a Class A boat requires not just a sailor’s hat but real skills and teamwork. Plus, these coveted spots usually go to locals, seasoned with experience and knitted tightly into the boat racing fabric of the community. There are plenty of other ways to get into the maritime mood:

  • Watching from the Shoreline: Grab a spot on Sandy Ground to watch these sleek vessels set sail. Or, better yet, find a vantage point along the course to catch them in full throttle.
  • Party Boat Patrol: Fancy a floating fiesta? Jump onto a party boat that chases the race around the island, complete with beats and beverages.
  • Festival Fever: Align your visit with the Anguilla Day celebrations or other festive races to enjoy a full spectrum of entertainment, beyond just the race.
  • Sponsoring a racing boat in Anguilla: Thinking of getting even closer to the action? While crewing might be off the table, you could try sponsoring a boat. It’s a great way to dip your toes into the local scene, especially if you’ve got some connections or meet someone in the know.
  • Volunteering at a boat race in Anguilla: If you’re all about that behind-the-scenes life, volunteering at one of the boat race festivals could be your backdoor to the excitement. It’s a win-win: help out, have fun, and maybe even get a closer peek at the racing action.

Just remember, whether you’re on a boat, by the beach, or volunteering, Anguilla’s boat racing scene is about soaking up the vibe, the view, and maybe a bit of sea spray.


Cycling in Anguilla

The unique geography of the Caribbean’s Anguilla asserts this quiet destination as a paradise for cyclists. It is, hands down, one of the most beautiful places in the Caribbean. Anguilla boasts 33 breathtaking beaches—that’s practically two per mile—along with vibrant neighbourhoods and picturesque spots ideal for catching the sunset. The ultimate way to truly immerse yourself in the splendours of Anguilla? Jump on a bike and start pedalling.

Wondering where to go cycling in Anguilla? The answer is everywhere, depending on your abilities! The north offers tougher routes and rewarding views of Shoal Bay—a perfect pit stop for some beachside chill. Swing to the west side for the island’s smooth operators: paved roads that make up 90% of your ride. This side’s where you’ll zip past the glitzy oceanfront hotels and dive into the retail heart of Anguilla. It’s essentially the luxury lane of biking, offering a plush ride with a view. Perfect for those who like their scenic pedal with a side of window shopping. Head east for the best views and the least traffic—it’s where the wild side of Anguilla shines.

 And if you’re worried about getting lost or tangling with traffic, fear not. The roads are mostly smooth sailing, but keep an eye out for the odd pothole. In Anguilla, Caribbean laid-back vibes meet pedal power in a cyclist’s tropical fever dream. With a terrain that toggles between lazy hills and flat stretches by the beach, it’s your call whether you’re in for a leisurely ride or an adrenaline fix.

Group cycling in Anguilla is a thing! Cycling is big on this dot in the Caribbean, thanks to the Anguilla Cycling Association. They’re the folks behind the scene, turning the island into a biking hub with races that draw the community together. Keen to join? They kick off group rides at dawn, covering 15 to 25 miles that cater to everyone from newbies to peloton pros. ACA’s the heart of it all, and they’re easy to find online for the latest on early rides and races.  You can find ACA on Strava ( ) and Facebook (

The cycling calendar in Anguilla culminates with the John T. Memorial Cycling Race every July is a tribute to local legend John Thomas. It’s not just a race; it’s an 80-mile marathon that puts stamina to the test, drawing cyclists from across the Caribbean. 

Renting a bike in Anguilla is a breeze! Shop around for wheels at local bike hubs, where $25 gets you a sleek road bike. For reputable rental shops, search online for :

  • At Bryans Car Rentals, you can snag a professional road bicycle for your island escapades. With choices like Trek, Origin8, and Giant, all for $25 a day, it’s like the VIP lounge of bike rentals. Ronnie Bryan is Anguilla’s bicycle guru with Commonwealth Games cred;
  • Anchor Miniature Golf and Boo’s Cars & Cycle Rentals also offer wheels for $20 to $25 a day;
  • Premier Mountain Bike Rentals have a good reputation;
  • Freedom Rentals has ATV quad bikes that promise a wilder ride. Whether you’re looking for a leisurely cycle or an adrenaline-pumping adventure, Anguilla has got you covered, pedal to metal.

In Anguilla, cycling is a great way to soak up the island in all its glory. Whether you’re crossing it end-to-end or just cruising for the perfect beach spot, it’s an exhilarating adventure on two wheels.



Ready for a golfing adventure in Anguilla? The Aurora Anguilla Resort & Golf Club is where you’ll find your happy place, especially if that place involves swinging clubs and chasing little white balls across breathtaking landscapes.

Where is the best golf course in Anguilla located? It fits snugly in Rendezvous Bay, and offers not one but two courses designed by golf legend Greg Norman. The International Course is like the VIP of golf courses—18 holes with views so stunning, you might forget to keep score. It’s recently been crowned the #2 Best Caribbean Course, so expect to be playing among golf royalty. Then there’s Avalon Links, a quirky little 9-holer that mixes short sprints with a marathon 300-yard hole, ensuring both seasoned players and newbies find their groove.

Wait, you want to learn golf in Anguilla? The Golf Academy at Aurora is packed with Trackman gadgets and gurus to shave strokes off your game. Whether you’re a lone wolf on the green or bringing the whole pack, they’ve got membership options to fit (Individual or Family, International or Full), so you can feel like the king or queen of the course.

Non-members, fear not. You can still swing by for a round by parting with some green (fees, that is). The club’s dining scene promises to ace your post-game analysis, serving up anything from victory burgers to consolation cocktails.

And what if you need to rent golf gear? For tennis lovers who are about to rock those fairways, Aurora has your back with rental gear that could make a pro blush. They’re talking about the TaylorMade Stealth series—because if you’re going to miss that fairway, at least do it in style. 

So, whether you’re aiming to conquer the International Course, flirt with Avalon Links, or just want to hit balls farther than you can see, Aurora’s got the greens, the views, and even the brews. Just remember to book ahead, as spots fill up faster than a sand trap at high tide. For the nitty-gritty on green fees and tee times, reaching out directly to Aurora is your best shot.



Anguilla’s tennis scene is a vibrant mix of local talent and international acclaim, anchored by the remarkable efforts of the Anguilla Tennis Academy (ATA). Since its inception in 1996 by local tennis star and entrepreneur Mitch Lake, the ATA has been pivotal in shaping the island’s tennis culture. This non-profit grassroots programme is committed to leveraging tennis for social transformation, offering opportunities for young Anguillians to shine both on and off the court.

Tennis in Anguilla has long been a favourite pastime, attracting enthusiasts from around the globe. But beyond its appeal among the island’s visitors, the sport has played a significant role in community development. The ATA, with its inclusive programmes, summer camps, and scholarship opportunities, has made tennis accessible to over 4,000 kids aged 5 to 17. This initiative not only nurtures athletic talent but also opens doors for educational advancement, mirroring Lake’s own journey through tennis.

The Anguilla Tennis Academy, or ATA, is synonimous with tennis excellence in the Caribbean. With state-of-the-art facilities, including six illuminated courts and a comprehensive training regimen, the academy has gained international recognition. The achievements of ATA graduates, many of whom have secured athletic scholarships in the U.S., are a testament to the academy’s impact. The state-of-the-art tennis facility now hosts the island’s premier tennis event, the Anguilla Cup, offering locals and visitors alike the opportunity to enjoy a week of world-class tennis.

Wondering where to play tennis in Anguilla? For tennis aficionados visiting Anguilla, the island offers prime facilities to enjoy the game:

  • Anguilla Tennis Academy (Blowing Point): This premier facility not only serves as a training ground for young athletes but also welcomes visitors for court rentals, lessons, and equipment hire.
  • Carimar Beach Club (West End): Guests at Twin Palms Villas enjoy complimentary access to championship courts at Carimar Beach Club, with potential availability for public rentals.
  • The Four Seasons Resort and Residences (Meads Bay) is a match made in heaven for those seeking a touch of luxury. This upscale resort not only features three tennis courts for guests to enjoy but also complements the experience with a fully equipped fitness centre and a range of water sports activities available through their Aqua Centre. 

Tennis lessons in Anguilla are available, as is equipment rental. Tennis lessons on the island are facilitated by the availability of lessons and equipment rentals through the ATA. They offer a range of options to suit individual and family needs. For those travelling without their gear, the academy provides equipment rentals, ensuring everyone can enjoy the sport.


Hiking in Anguilla

Anguilla’s coastal hikes offer a stunning alternative to the beach scene. Imagine turquoise water lapping against dramatic cliffs, with hidden coves waiting to be explored.  Anguilla might not shout about its hiking trails from the rooftops, but that’s exactly what makes venturing off the beaten path here so special. It’s the island’s best-kept secret, offering serene escapes with mesmerising views, minus the crowds. 

The best season for hiking in Anguilla is the dry season, between mid-December and mid-April. The weather’s on your side—think clear, sunny days with just the right amount of breeze to keep you cool. Perfect for avoiding sweaty treks and maximising those ocean vistas.

Anguilla’s hiking trails are not well-known world-wide, but if you’re willing to explore, you’re in for a treat. It’s like finding your own private slice of paradise, with the bonus of heart-pumping trails and eye-popping views. Grab a map, rent a moke, and head west to discover spots like the Arch—a photographer’s dream perched on a narrow stretch of land amidst the ocean.Here are some routes where the journey is just as good as the destination:

  • Rendezvous Bay to Maundays Bay: A leisurely stroll or a brisk walk, this trail serves up beach vibes and bird-watching opportunities. Plus, ending at Maundays Bay isn’t too shabby.
  • Little Harbour Trail: Ideal for families or anyone after a chill vibe, this path has scenic stops perfect for dipping your toes in the water or just soaking in the tranquility.
  • Shoal Bay to Gwen’s Bay: Linking two of Anguilla’s beach jewels, this trail offers the best of sandy shores and secluded spots for a mid-hike break.
  • Viceroy’s Residencies Beach to Meads Bay: Short, sweet, and straight to the point of beach bliss. This trail is a quick hit of coastal beauty.
  • Cove Bay to Captain’s Bay: Brace yourself for a moderate challenge and rewards in the form of stunning cliffs and two very different beach atmospheres.

The Anguilla National Trust ( focuses on preserving the island’s natural environment and cultural heritage. While they don’t maintain hiking trails themselves, hiking trips can be booked via them.


Diving and Snorkeling in Anguilla

Anguilla’s calling card? Breath-taking turquoise waters. But this beauty isn’t just for sunbathers. The consistent 27°C (80°F) water temperature makes every day a potential dive or snorkel day. Plus, Anguilla takes marine conservation seriously. Dive operators are not just guides but also environmental champions actively involved in local programs. Some even run educational sessions for youngsters, fostering a future generation of ocean protectors.

The best time for diving and snorkelling in Anguilla is generally considered to be the dry season, which runs from mid-December to mid-April. During this period, you’ll experience sunny skies, calm seas, and excellent underwater visibility. Water temperatures also tend to be warmer during this time, making for a more comfortable snorkelling and diving experience.

Snorkelling in Anguilla’s marine parks is a technicolour dream. Teeming with marine life, these protected areas are perfect for divers of all levels, even those who prefer to keep their hair mostly dry.

Want a guided adventure? Hop on a boat trip to explore hidden underwater worlds. Feeling more “beach bum”? No worries; many coves and bays offer stunning snorkelling right off the shore. For the adventurous, private charters with dive shops like Scuba Shack whisk you to secret spots and iconic landmarks. Take the plunge from Jumping Rock in Little Bay (nicknamed LeBron Rock after a certain basketball star’s daring leap!) or explore the vibrant reefs of Pelican Bay.

Best Locations for Snorkelling in Anguilla:

  • Shoal Bay East: This calm bay boasts a beautiful reef teeming with fish, making it a great spot for all ages and swimming abilities. The reef starts around 150 feet offshore and is easily accessible by swimming.
  • Little Bay: This secluded beach offers clear waters and a healthy reef system with colourful fish and coral formations. Getting to Little Bay requires climbing down a rope ladder or using a water taxi, but the snorkelling rewards are worth the effort.
  • Sandy Island: This tiny island is a popular spot for snorkelling trips. The calm waters surrounding the island offer opportunities to see colourful fish, coral reefs, and stingrays.
  • Maho Bay: This protected bay is a great choice for families with young children. The calm and shallow waters provide a safe environment to explore the underwater world, spotting colourful fish and coral formations.
  • Captain’s Bay: This picturesque beach boasts a fringing reef with an abundance of marine life. Snorkelers can expect to see colourful fish, turtles, and even the occasional eagle ray.

Wreck diving in Anguilla offers a unique opportunity for scuba enthusiasts. In the late 1980s, a collaborative effort between the Anguillian government and a local dive shop led to the discovery and repurposing of multiple shipwrecks. These wrecks were meticulously raised and strategically placed to create seven distinct dive sites, transforming them into vibrant artificial reefs. This innovative approach to shipwreck management not only extended the lives of these vessels but also enriched Anguilla’s underwater environment.

The Best Locations for Diving in Anguilla:

  • Dog Island: West Cay and Devil’s Wall are two of the best dives in Anguilla, located off Dog Island. Both sites are accessible to all diving levels and descend about 80 feet to the sea floor. Divers can encounter stingrays, sharks, and a variety of colourful reef fish. 
  • Lighthouse Reef: This vibrant reef teeming with marine life is perfect for divers of all experience levels. Located near Sandy Island, it features coral formations, caves, and swim-throughs. Look out for colourful fish, lobsters, turtles, and even nurse sharks. 
  • Shoal Bay Reef: This underwater paradise boasts coral bommies, swim-throughs, and a variety of marine life. Divers of all levels can enjoy exploring this reef, encountering colourful fish, turtles, rays, and octopus.
  • Mimi’s Reef: This fascinating site features a shipwreck and an abundance of marine life. Intermediate to advanced divers can explore the wreck and surrounding reef, spotting colourful fish, lobsters, turtles, and eagle rays.
  • Sandy Island: This small island offers great wall dives along its eastern and western sides. Suitable for advanced divers, these walls teem with fish, sharks, and crustaceans.

What sea life can you see in Anguilla? The waters around Anguilla boast a rich and diverse marine life, making it a snorkeler’s and diver’s paradise. Here’s a glimpse of what you might encounter:

  • Colourful Reef Fish: Anguilla’s reefs are home to a stunning variety of colourful fish, including angelfish, butterflyfish, parrotfish, damselfish, and wrasses.
  • Turtles: Hawksbill and green sea turtles are frequent visitors to Anguilla’s waters. Spotting one of these majestic creatures while snorkelling or diving is a truly unforgettable experience. 
  • Stingrays: Southern stingrays are commonly encountered in the sandy areas around Anguilla’s reefs. These gentle giants are a fascinating sight to see while underwater.
  • Sharks: Several species of sharks, such as nurse sharks and reef sharks, can be seen while diving in Anguilla. These sharks are typically not aggressive towards humans and are an important part of a healthy marine ecosystem.
  • Lobsters and Spiny Lobsters: Keep an eye out for lobsters and spiny lobsters hiding amongst the coral crevices.
  • Octopus: The curious octopus is another resident of Anguilla’s reefs.

Choosing your dive guide in Anguilla is crucial for a safe and enjoyable underwater experience. Here are some top choices to consider:

  • Scuba Shack (Shoal Bay): A PADI-certified dive centre located in Sandy Ground. They offer courses for all levels, from beginner Discover Scuba Diving to advanced certifications. They also provide equipment rentals and guided dives to Anguilla’s most popular sites.
  • Shoal Bay Scuba (Shoal Bay): Anguilla’s only full-service PADI Dive Resort. They offer a comprehensive selection of courses, from beginner to professional levels. Their well-equipped dive shop has rental gear and guided dives for all experience levels.
  • Vigilante Divers (Sandy Ground): Ideal for experienced divers seeking a personalised experience. They offer private charters and guided dives to Anguilla’s best dive sites.


Island Hopping in Anguilla

Anguilla’s charm extends beyond its main island. Every visitor should try and explore the diverse offerings of its six offshore islands, each catering to a different adventure:

  • Dog Island: Birdwatcher’s Paradise. This island boasts a symphony of feathered friends, from sooty terns to brown boobies. Experienced divers can explore its underwater wonders.
  • Sombrero Island: Wildlife Watching & Diving. Sombrero Island, a haven for nesting seabirds designated as an important bird area, is also a feeding ground for Hawksbill turtles. 
  • Prickly Pear Cays: Snorkel & Dine. Pristine snorkelling spots and two delightful beachfront restaurants serving fresh seafood and tropical cocktails await you on Prickly Pear.
  • Scrub Island: Unwind & Explore. Escape the crowds on uninhabited Scrub Island. Observe wildlife, snorkel with stingrays, and discover hidden lagoons.
  • Sandy Island: Relax & Refuel. This laid-back island offers a perfect afternoon getaway. Grab a bite at the island’s restaurant, chill on the beach, or explore the calm waters for a relaxed snorkelling experience.
  • Anguillita: Snorkel & Dive. Anguillita, the southernmost island, is a haven for snorkelers and divers seeking a remote adventure. Completely uninhabited, it provides a true “end of the earth” feel.

How can you go island-hopping in Anguilla? Island-hopping tours are readily available in Anguilla. Many resorts and tour operators offer day trips to these stunning islands.

Reputable tour operators in Anguilla include:

  • Anguilla Offshore Adventures offers a variety of island-hopping tours catering to different interests.
  • Tranquility Boat Tours: Known for their relaxed atmosphere and scenic journeys.
  • Shoal Bay Scuba specialises in diving expeditions and eco-friendly tours focused on marine conservation.
  • Calypso Charters specialises in wildlife viewing tours, including trips to Sombrero Island.
  • Funtime Charters offers morning or afternoon excursions to nearby islands like Sandy Island.
  • Tranquillity Boat Tours (Private Charters): Craft a personalised island-hopping itinerary for a unique experience.

Can you rent your own boat in Anguilla? Absolutely! Several companies offer boat rentals with or without a captain. However, navigating unfamiliar waters and reefs requires experience. Consider a guided tour for a stress-free adventure. Boat rental companies that have a good reputation on the island are Island Time Boat Rentals and Sandy Ground Provision. 

by Elena Leo, WAWW Direcotr of Editorial

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