Things to Do in Anguilla

The British overseas territory of Anguilla features spectacular Amerindian rock art, multifaceted Afro-Euro-West Indian cuisine, blissful mainland sands, and idyllic offshore cays. There’s much to do, experience and explore here. 

Here at WIMCO, we have been serving and helping our customers plan their vacations in Anguilla for over 35 years. And we decided to share our wealth of knowledge, experience, and insider tips. 

So to help you plan and prepare, we’ve put together the very best things to do in Anguilla. After reading through this WIMCO guide, you’ll be set to get the most out of your visit to this sun-splashed corner of the Lesser Antilles!

Here Is What We Will Cover:

Top 12 Things To Do In Anguilla

Wondering what to do in Anguilla? We’ve got you covered! From snorkeling and surfing to guided excursions, tours, and day trips, here are a dozen of the best Anguilla activities.

1. Go Horseback Riding on the Beach: Saddle Up & Go

Go Horseback Riding on the Beach: Saddle Up & Go

Caption: Horseback riding on the beach in Anguilla

Overview:  Strolling an idyllic Anguillan beach on your own two feet is fine enough. Imagine hoofing it over the sands and even in the water, on the back of a mild-mannered horse! That’s the unforgettable experience offered by Seaside Stables on the southwest coast along Cove Bay. Whether you have any experience on horseback, you’ll be just fine on one of these gentle, well-trained animals as you’re guided out onto the beachfront.

The stable offers several different beach rides, including an especially mesmerizing moonlit option. If you’re so inclined, spring for the ride that includes a horseback dip in the Caribbean!

Duration:  Half-hour to one hour.

Perfect For:  Couples, families.

Why Go:  There’s something magical about horseback riding on a tropical beach, lulled equally by the saddle’s rhythm and the breaking waves.

Insider Tip:  If you do decide to take a swim with your horse, wear loose-fitting clothing for a more comfortable ride back…and don’t forget to wear a hat 

2. Go for a Sail: Experience Anguilla’s Quintessential Pastime

Overview:  From fishing and maritime trade to the more nefarious activities of pirates and smugglers, sailing is firmly rooted in Anguilla’s history. Today it remains an immensely popular activity both from sightseeing and sporting standpoints. For sailboat racing fans, the annual Anguilla Regatta offers quite the spectacle.

It’s a joy to catch the trade winds and smell the salty air on a boat in Anguillan waters. You’re spoiled for choices when it comes to sailing charters, from public cruises to private custom outings. Meanwhile, the Anguilla Sailing Association offers lessons for aspiring sailors at Sandy Ground.

Duration:  Few hours to a full day.

Perfect For:  Couples, families, any mariners (beginner to advanced).

Why Go:  It’s wonderful to enjoy Anguilla’s beachfront from the shore, but getting out on the water in the same manner as centuries of Caribbean seafarers have—well, that’s more magical yet! 

Insider Tip:  Charter sailboats such   as the  Chocolat  and  Tradition  offer sunset sails and layovers on offshore beaches such as the Prickly Pear Cays.

3. Take in a Caribbean Sunset: Evening Sky Pageantry From the Beachfront (or the Water)

Take in a Caribbean Sunset: Evening Sky Pageantry From the Beachfront (or the Water)

Caption: Beautiful sunsets in Anguilla

Overview:  Anguilla’s long west-facing coastline gives you a sublime location from which to view some world-class Caribbean sunsets. Seeing the sun slip below the liquid aqua-colored horizon can be breathtaking. Even though it’s a daily occurrence, an Anguilla sunset never gets old!

Barnes, Meads, Shoal, and Rendezvous bays as well as Sandy Ground are the top beaches for sunset-viewing. As we’ve mentioned, sailing charters and other boat tours usually offer sundown cruises.

Duration:  Half-hour or so.

Perfect For:  Anybody!

Why Go:  Watching the sun go down over the Caribbean Sea is the perfect way to cap off another blissful day in the Leeward Islands. It’s certainly a spectacular time to head for the beach (unless you’ve been there all afternoon!). And from a sailboat or yacht, you find yourself surrounded by Caribbean waters gleaming with the glow from the sunset.

Insider Tip:  West-facing beaches or boats off Anguilla provide an excellent vantage for spotting the elusive “green flash” around sunset. This optical phenomenon, caused by atmospheric refraction, is an emerald streak occasionally seen above the sun as it’s sinking below the horizon. Extremely flat skylines such as Anguilla’s Caribbean backdrop offer the best chances of seeing the green flash.

4. Go Snorkeling & Diving: Anguilla’s Underwater Amazements

Go Snorkeling & Diving: Anguilla’s Underwater Amazements

Caption: Snorkeling in Anguilla

Overview:  Anguilla offers top-notch snorkeling and it’s one of the Caribbean’s most underrated diving destinations. Among the stellar snorkeling spots are Little Bay and Barnes Bay, and of course, the Prickly Pear Cays and Sandy Island.

Scuba lovers, meanwhile, can go deeper at sites such as Shoal Bay and Angel Reef, plus Oysterdeep Wreck, the 232-foot-long  Sarah , and various other shipwrecks. Farflung Dog Island to the west of the Prickly Pear Cays is a fascinating place to dive. WIMCO’s concierge team will be happy to arrange a private or group diving trip if you’d like!

Duration:  Few hours to half a day.

Perfect For:  Families (snorkeling), divers, ecotourists, photographers.

Why Go:  From coral reefs and seagrass beds to shipwrecks, Anguilla’s marine zone offers productive habitat for sea life. Snorkelers and divers often see spiny lobsters, stingrays, spotted eagle rays, sea turtles, and dolphins. 

The underwater walls of Dog Island are known for their big fish, including tarpon and sharks. You might even glimpse the mighty tiger shark—king of the Caribbean—in the deeper waters around wrecks.

Insider Tip:  If you’re not up for snorkeling or diving, consider going on a glass-bottom boat tour—the next best thing!

5. Go Surfing or Stand-up Paddleboarding: Ride the Waves

Overview:  Anguilla is an under-the-radar sort of surfing destination. While not offering quite the caliber or variety of the Caribbean’s best-known surf spots, the island can be a very rewarding place to ride the waves. That’s partly due to Anguilla’s position up at the top of the Leewards, receiving the full force of northerly swells. 

Prime spots include the reef break at Savannah Bay and the shore break and point break at Meads Bay. Options for stand-up paddleboarding (SUP) are all the richer, with the many tranquil bays and coves perfectly set up for this easygoing sport.

Duration:  Few hours.

Perfect For:  Watersports enthusiasts, couples.

Why Go:  The uncrowded aspect of Anguilla’s surf breaks is a major draw. Another way to enjoy the water is Paddleboarding, a sport accessible to anybody.

Insider Tip:  In Island Harbour, Surf AXA offers surfboard rentals, lessons, and surf tours. The company is a great resource for anyone interested in Anguillan board-riding.

6. Beach-Hopping in Anguilla: Pitch-Perfect Caribbean Sands

Beach-Hopping in Anguilla: Pitch-Perfect Caribbean Sands

Caption: Rendezvous Bay, Anguilla

Overview:  Anguilla boasts more than 30 beaches, adding up to more than a dozen miles of sandy shoreline. Among them are some of the top-ranked beaches in the Caribbean. Indeed, Anguilla’s Shoals Bay East often lands on lists of the best beaches in th e world . Other beloved beachfront include Cove-, Meads-, Barnes-, and Rendezvous bays.

Many beaches offer beach-gear and watersports rentals, plus easy-to-access restaurants, bars, and other services. Sheltered bayfront sands aren’t only fine for sunning and beachcombing: Many also provide excellent snorkeling opportunities. 

Whether you’re more into kicking back in the sand (or at a beachfront bar), or you’re feeling active enough for paddleboarding or kitesurfing, Anguilla’s sands are universally appealing.

Duration:  Few hours to a full day.

Best For:  Anyone seeking premium Caribbean R&R.

Why Go:  It’s easy to see the appeal of a day spent lounging on glossy, sun-warmed sands alongside turquoise Caribbean waters. Anguilla’s abundance of beaches ensures there’s the perfect spot for your wants, whether a resort-lined party beach or an out-of-the-way, lightly developed strand. 

Savannah Bay is a great choice for a more pristine-feeling beachfront. And, as we’ve mentioned, the west-facing beaches of Anguilla offer fabulous sunset views!

Insider Tip:  Don’t forget the straight-out-of-paradise beaches found on Anguilla’s easily reachable offshore islets such as the Prickly Pear Cays and Sandy Island.

7. Play a Round of Golf: The Joys of Anguilla Greens & Fairways

Golfing in Anguilla

Caption: Golfing in Anguilla

Overview:  What could be better than teeing off with views out over the Caribbean Sea? That’s the sheer pleasure of a round or two of golf on Anguilla. A Greg Norman-designed course, The Anguilla International Golf Club holds its own weight with any in the West Indies.

This 7,093-acre, 18-hole golf course, set on Rendezvous Bay, also includes a nine-hole beginner-friendly Greg Norman Signature Short Course.

Duration:  Couple of hours (plus).

Perfect For:  Golfers (naturally).

Why Go:  The Anguilla International Golf Club is frequently ranked among the best golf courses in the Caribbean. Hit up the greens here, and you’ll quickly see why! The scenery here includes stunning views of mountainous Saint Martin.

Insider Tip:  If you’re a truly golfing enthusiast, tack on a day trip out to the Four Seasons Resort on Nevis. Its nice course is only a short flight away via Trans Anguilla Airways.

8. Swim With Dolphins: Make Some New Finned Friends

Overview:  While you have a chance of seeing wild dolphins in the waters around Anguilla, there’s also a surefire way not only to see them but play with them. Visit Dolphin Discovery along the Blowing Point beachfront on the island’s south shore.

This park offers several different swimming-with-dolphins experiences, including games, dolphin hugs and kisses, belly rides, and more. Playing outright in the Caribbean, these interactive bottlenose encounters easily rank among the top family-friendly Anguilla activities.

Duration:  Half-hour to 40 minutes.

Perfect For:  Families.

Why Go:  For more than a few folks, swimming with dolphins is a genuine bucket-list item. Dolphin Discovery can make it happen during your Anguilla getaway. The “Royal Swim” is the deluxe experience, including the foot-push. That’s where the park’s resident dolphins power you through the water with their snouts: an exhilarating sensation!

9. Visit the Old Factory: Pay Your Respects to an Anguillan Landmark

Overview:  Situated at Government Corner along The Valley Road, the Old Factory is a handsome but unassuming building with rich history. This structure was built in the early 1900s to serve as a general store and trading center adjacent to Anguilla’s cotton gin. Anguilla cotton was highly coveted around the world at the time.

Now housing a real-estate office and art gallery, the Old Factory is part of the self-guided Anguilla Heritage Trail. (Stops along it come marked by signs with an “H” encircled by dolphins.) The building was damaged but not destroyed in Hurricane Irma, and has been nicely restored.

Duration:  Half-hour.

Perfect For:  History buffs, art lovers.

Why Go:  Besides its historical significance, the Old Factory is worth checking out for its Stone Cellar Gallery. Here you’ll find paintings by the noted French-Caribbean  plein-air  artist Sir Roland Richardson. Furthermore, the Old Factory is just a stone's throw from one of Anguilla’s other best-known historical landmarks, the Wallblake House.

Insider Tip:  The Old Factory at Government Corner is not to be confused with the Old  Salt  Factory & Pumphouse in Sandy Ground. But, now that we’re mentioning it, that’s another of the premier Anguilla attractions for students of history.

10. Explore the Heritage Collection Museum: A Fascinating Treasure Trove of Anguillan History

Overview:  Established in 1996, the Heritage Collection Museum in East End Village is Anguilla’s very own top-notch history museum. We can thank historian Colville Petty O.B.E., its founder and dedicated curator for the diversity of its collections and clarity of interpretive materials.

The museum displays a wide range of artifacts: from pottery and dishware to cannons and fishing boats. And it covers a great sweep of time, from the deep past of the Taino and Arawak peoples through colonial agriculture and slavery, up to the present day. 

A wealth of newspaper clippings, photos, and other documents tell the story of the 1969 Anguillan Revolution and the resulting British military invasion.

Duration:  At least an hour or two.

Perfect For:  History buffs, anyone looking to more deeply understand Anguilla.

Why Go:  A visit to the Heritage Collection Museum can add immeasurable depth and context to your Anguilla getaway. Mr. Petty does a fine job introducing visitors to the museum, providing overviews on Anguilla’s history, and fielding questions. Along with assorted souvenirs, you can also buy some of the books Petty’s penned in the museum shop.

Insider Tip:  The building’s exterior, painted in the colors of the Anguillan flag, makes a nice photo op.

11. Go Shopping: Pick Up Arts, Crafts, Souvenirs, and More

Overview:  Anguilla isn’t among the Caribbean’s best-known shopping destinations, but you will find a nice range of wares here—from locally made crafts to stylish beachwear. There are quite a few boutiques, souvenir shops, galleries, and even a large discount store on the island.

Irie Life is among the standout shops to visit, known for its array of clothing, giftable, and trinkets. The Anguilla Arts & Crafts Center features local artists and makers, while Cheddie’s Carving Studio sells one-of-a-kind driftwood and coral sculptures.

Duration:  Few hours to a full day.

Perfect For:  Souvenir shopping, outfitting yourself in Caribbean fashion.

Why Go:  If you forgot beachwear or other essentials, Anguilla’s shops have your back. And you’ll have abundant opportunities to find the perfect souvenirs and exotic gifts for folks back home.

Insider Tip:  An easy ferry ride from Anguilla will take you to the famed duty-free shopping hotspot of Saint Martin.

12. Go Kiteboarding: Catch the Wind

Kiteboarding in Anguilla

Caption: Kiteboarding in Anguilla

Overview:  The steady trade winds that provide a pleasant, moderating breeze on Anguilla also make for top-shelf kiteboarding conditions year-round! Whether you’re a complete newbie or a veteran kitesurfer, the island’s a great place to indulge in this adrenaline-pumping watersport.

There are plenty of good kitesurfing spots, from mainland locations such as Blowing Point and Meads bay to offshore cays. Anguilla Watersports offers the island’s only kiteboarding academy, with lessons for all experience levels.

Duration:  Few hours.

Perfect For:  Watersports enthusiasts, thrill-seekers.

Why Go:  You can catch some major air off postcard-perfect beaches by Harnessing Anguilla's coastal wind. Kitesurfing is a nice workout, too, though you’ll be having too much fun to notice.

Top Excursions In Anguilla

With an Anguilla luxury villa or hotel suite, you’ve got a well-appointed launchpad for some fabulous Lesser Antillean excursions. Those include offshore adventures to neighboring islands: from tiny nearby cays to other high-profile Caribbean nations. Here are some of the top Anguilla excursions and day trips!

Sandy Island

From the beach at Sandy Ground, a pleasant boat ride west-northwest takes you to irresistible Sandy Island. This smudge of sand on the Anguilla Bank can fulfill your ideal of a secluded tropical island paradise. Have a delish meal (and a rum punch) at the restaurant—Sandy Island’s only structure—and enjoy ace snorkeling on the nearshore reefs.

Prickly Pear Cays

Prickly Pear Cays

Caption: A visit to Prickly Pear Cays in Anguilla ©

The two Prickly Pear Cays draw day-trippers west of Anguilla. Common stops on charter boat tours, the Prickly Pear Cays are fantastic for both R&R and ecotourism. Besides their eateries, the islets have lovely beaches, rich birdwatching, and exceptional Anguilla snorkeling and diving.

Scilly Cay

Easily accessible from Island Harbour, the private islet of Scilly Cay will have you swooning. Its beautiful tropical vegetation and sandy beach set the right mood. Then there’s the Scilly Cay restaurant, acclaimed for its mouthwatering grilled lobster. You can even rent the cay out for special events!

St. Barths

Travelling to St. Barths from Anguilla ©

Caption: Travelling to St. Barths from Anguilla ©

Take a ferry, charter boat, or plane to the beloved French West Indies getaway of St. Barths, only 27 miles to the south. Here you can take in the lush, rugged scenery—strikingly different from Anguilla’s—and enjoy impeccable beaches, fine restaurants, and great shopping.

Best Things To Do In Anguilla For Families

Anguilla can be a wonderful place to bring your kids. After all, white-sand beaches and Caribbean surf have a way of minting lifelong family memories. Here are some of the best things to do in Anguilla with the entire crew!

Water Activities

From playing in the shallow calm waters to swimming to stand-up paddleboarding to kitesurfing, Anguilla offers a slew of family-friendly activities and recreation. The options, of course, include the mentioned Dolphin Discovery experiences. And it’s not just about that stellar seashore: Anguilla’s Aqua Park is the Caribbean’s biggest inflatable waterpark and a surefire kid-pleaser.

Best Anguilla Beaches for Smaller Kids

Kids enjoying the beach in Anguilla

Caption: Kids enjoying the beach in Anguilla

Anguilla’s wealth of sheltered beaches make many of its sandy seashores ideal for the younger crowd. Among the best beaches in Anguilla for smaller kids are those along Savannah Bay, Cove Bay, and Shoal Bay.

Anguilla Tours for Families

From surfside horseback rides to sailing cruises and guided snorkeling trips, many Anguilla tours are ideal for families. These can be fun-filled ways to explore the island and its waters all together.

Look for Wildlife

Young and old alike tend to get excited about spotting animals in the wild. Anguilla’s wildlife ranges from anole lizards and Antillean crested hummingbirds to tropical fish, dolphins, sea turtles, and sharks. Good destinations include the Prickly Pear Cays, host to raucous seabird colonies and abundant reef life.

Play Mini Golf

Ah, miniature golf: right up there among the truly classic family-vacation activities. Anguilla’s Anchor Miniature Golf in Island Harbour is a solid option.

Most Romantic Activities In Anguilla For Couples

The laidback vibe, uncrowded shores, and swoony Caribbean scenery make Anguilla ideal for romantic getaways. Here are our picks for the top couple's activities on the island!

Secluded Beaches

World-class (but often quiet) beaches with a sizzling Caribbean swash: What more could you ask for in the romance department? More secluded-feeling Anguilla beaches ideal for lovebirds include Barnes Bay Beach, Rendezvous Bay, and Little Bay Beach.

Spa & Wellness

Side-by-side couples massage, anyone? Romantic Anguilla wellness experiences could take the form of spa services in your private villa, or a visit to any of the resort or day spas.


Dining Out

Dining out at Pimms, Hotel Belmond Cap Juluca, Anguilla

Caption: Dining out at Pimms, Hotel Belmond Cap Juluca, Anguilla

Romantic meals in unforgettable settings that are also delicious is easy to come by on Anguilla. From internationally acclaimed Blanchard’s and Cap Juluca’s seductive Pimms to Trattoria Tromonto’s beachfront Italian meals, you’re spoiled for choices.

Sunset Cruise

Enjoy a sunset cruise in Anguilla

Caption: Enjoy a sunset cruise in Anguilla

Flawless beaches and sublime sunsets are Anguilla’s two most potent romantic attributes. Besides combining them with day’s-end beach-going, take advantage of one of the many sunset cruises tour companies and charters offer.

Uniquely Anguilla Experiences

Certain Anguilla activities seem to sum up the magic of this island. And certain destinations here are absolutely one-of-a-kind. Here are a few examples of these signature Anguilla attractions and experiences.

Little Bay Beach

Among the loveliest and most secluded Anguillan beaches, Little Bay’s bluff-backed sands in the northwest can only be reached by boat. It’s worth the effort, for sure!

Fountain Cavern National Park

Among the Caribbean’s most significant archaeological sites, Anguilla’s Fountain Cavern includes a subterranean pool long used by Amerindians for freshwater. Its limestone exposures also come patterned with enigmatic indigenous petroglyphs. 

Visitors to Fountain Cavern National Park can learn more about this precious piece of Anguilla’s heritage via interpretive exhibits.

Heritage Collection Museum

The Heritage Collection Museum adds color and dimension to anybody’s visit to Anguilla. If you want to go beyond sand and surf in understanding the island, Colville Petty’s curation is just the ticket.

Old Factory

Tap into Anguillan history at the Old Factory—and admire some fine Caribbean art as you do!

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