Don’t let Anguilla’s diminutive size deceive you. At just 33 sq miles, the island is home to world-class beaches, a vibrant music scene, and an enchanting blend of luxury and authenticity. It's a haven for honeymooners and romantic escapes but also appeals to families and multigenerational groups seeking something beyond the ordinary.
Ask any of the devout repeat visitors and they’ll wax lyrical about this off-the-beaten-path Caribbean gem. Its location, far enough from neighboring St. Maarten, means Anguilla side steps mass tourism, focusing more on independent and boutique offerings. You won’t find casinos, cruise ships or nightclubs here. Instead, you’ll discover Anguilla’s brand of cool: a destination that practically defines barefoot luxury and celebrates life’s simple pleasures.
Here are the top things to do on a getaway in Anguilla.
Discover Anguilla’s world-famous beaches
For any traveler who doesn't consider themselves a beach lover, Anguilla’s pristine white beaches will convert you. At just 16mi long and 3 mi wide, the island is home to 33 beaches which means you’re never far from a stunning stretch of sand.
For those seeking the ultimate in picturesque destinations, Anguilla’s most celebrated beaches, including Meads Bay, Shoal Bay and Rendezvous Bay, have garnered lots of love for a reason. On each, you’ll find restaurant outposts with beach chairs where you can spend the day slipping between the sun and the sea pre- or post-dining.
For those who want more adventure, grab a rental car and head out to explore. When driving in Anguilla you'll be reminded that this is still a British Overseas Territory – don’t forget to drive left!
The eastern end of the island offers a range of beaches perfect for explorer spirits. Head to Captain’s Bay for a rugged end-of-the-world vibe where you’ll likely be rewarded with a beach all to yourself.
Taste your way through the island
Anguilla’s impressive dining scene takes some visitors by surprise. With chefs from around the globe calling the island home, the biggest challenge is fitting in your dining wish-list into a single visit.
Chef-proprietors run many of the island’s restaurants and take pride in consistently putting out fabulous food. For fine dining, don’t miss Jacala, a French restaurant on Meads Bay that offers a long, drawn-out lunch. Prepare for a bottle of rosé and a multi-course meal that’s bound to be your day’s most important affair.
Ember Restaurant, helmed by chef Marc Alvarez, is a must for dinner. Offering wood-fired cuisine that celebrates local ingredients, you might find specialties like wood-roasted crayfish scampi alongside lavender-braised lamb shank on its seasonally changing menu. Nab a pre-dinner aperitivo at the bar before sliding into an outdoor table and relaxing for the remainder of the night.
For a more casual approach to dining, try Picante, a taqueria with Caribbean influences doling out pitchers of serrano margaritas and specialties like double-decker fish tacos prepared with fresh grilled mahi.
Tap into Anguillian history and culture at the National Trust
The Anguilla National Trust was founded in 1989 with a focus on sustaining the island’s cultural heritage. In addition to research and conservation work, the ANT, located in the former Customs Building in the Valley, offers hikes and opportunities for visitors and locals to engage in conservation projects.
For wildlife enthusiasts, check out opportunities to participate in their Sea Turtle Monitoring Program during nesting season. For lovers of history and heritage, the ANT’s Heritage Tour focuses on Anguilla’s history from the Amerindian era to the island’s colonial past and brings to life to sometimes overlooked buildings and monuments.
The National Trust’s hiking tours take place all around the island and occasionally head to off-island cays like Dog and Scrub Islands.
Explore the island by boat
Just one glimpse of Anguilla’s neon-hued seas and you’ll quickly realize that not all beaches and coastlines are created equal. Anguilla’s crystalline waters are straight out of a postcard and there’s no better way to explore than by boat.
The island’s small size means that you can visit a range of beaches, hidden coves and off-island cays in a single day for a mix of sun, sand and snorkeling. Don’t miss a stop at Little Bay (a very secluded beach) and a quick zip by Anguilla’s arch formation on the island’s West End.
Head to Prickly Pear for lunch on one of Anguilla’s enchanting off-island cays for a BBQ on the beach. Spend the afternoon snorkeling off the shoreline or visiting the oft-overlooked caves en route.
Alternatively, on the main island, enjoy lunch at Falcon’s Nest in Island Harbour, a casual restaurant owned by local fishermen situated within the island’s primary fishing village. Funtime and Calypso both offer private boat charters that generally seat up to 12 passengers.
Cruise to Anguilla’s off-island cays
If you thought Anguilla felt remote before, wait until you experience the islands off of the island. For the ultimate desert island experience, head to one of three primary off-island cays: Scilly Cay, Sandy Island or Prickly Pear.
Each island has its own personality and all three offer dining options to make a day of the experience. Generally open just two days per week, Scilly Cay is known for serving up one of the island's best lobster lunches alongside its famed rum punches.To reach Scilly, take a small shuttle from Island Harbour’s pier on the island’s eastern side.
Sandy Island brings an Instagram-worthy backdrop with its colorful beach hut and photogenic corners. You’ll be spoiled for choice thanks to an extensive menu, but fan favorites include the classic Anguillian go-tos like local crayfish (a regional specialty) or traditional BBQ with chicken and ribs.
Prickly Pear is more difficult to reach – you’ll generally need to go by private boat – but you’ll be rewarded with one of the island’s most beautiful beaches, hidden caves and family-style lunches for groups.
Uncover the beauty of Little Bay
Little Bay, situated on the island’s north shore, is accessible only by water – unless you count the rock-mounted rope that allows you to rappel down to its beach.
With stunning, rugged rock formations and a picture-perfect crescent-shaped cove, Little Bay is a truly unique landscape on the island. For the active adventure-seeking bunch, climb your way to the top of the rock at Little Bay to take the plunge, a rite of passage for many visitors to this picturesque enclave.
You can travel by boat to reach Little Bay as part of a bigger boat trip or rent a paddleboard from nearby Da ‘Vida in neighboring Crocus Bay to reach the cove by your own power.
Go horseback riding on Cove Bay
For more than 25 years, Tonia of Anguilla’s Seaside Stables has operated a private ranch in Anguilla. Set on Cove Bay on the island’s western side, nine horses call Seaside Stables home. Visitors, including families with children, can sign up for beach rides to explore the shoreline or dip into the sea. Rides can be catered to all levels so novices are as welcome as expert riders. For a serious wow, take a private ride at sunset.
Try your hand at watersports
Anguilla provides a perfect backdrop for active travelers who prefer to take their workout to the sea. Try stand-up paddleboarding or kitesurfing. For newbies, Anguilla’s conditions make it a perfect destination to learn how to kitesurf and Anguilla Watersports’ Kiteboarding Academy will get you on the sea with a pro.
For something a little smoother, try their paddleboard tour from Crocus Bay to Little Bay and end your tour at one of the island’s most-beloved marine preserves.
Get pampered at the spa
At its core, Anguilla is about downshifting and celebrating a slower pace of life. If you’re a traveler that needs some help with unwinding, spa services may do the trick. Many of the island’s five-star resorts offer a bevy of spa services, but none is more captivating than Zemi Beach’s Thai House Spa.
Housed in a 300-year-old Thai house, the spa is home to the island’s only hammam (steam bath) with a classic hammam package that offers a cleanse, clay body mask and massage. Book your treatments early so you can reap the benefits of your newfound relaxation.
Scope out Anguilla’s best beach bars
One of Anguilla’s most captivating truths is that it blends casual and glamorous seamlessly. You’re likely to have breakfast at your hotel, lunch at a beach shack, dinner at an upscale restaurant, and then head to a no-frills beach bar.
It’s that very essence that has captivated visitors to the island and made it a go-to for a broad range of travelers. So, where exactly are the best beach bars in Anguilla?
In the evening, visit Sandy Ground, the country’s main harbor and the closest thing the island has to a nightlife hub. Here you’ll find Elvis’ Beach Bar, a long-time favorite on the island. You’ll find a range of cocktails at the boat-turned-bar but you can’t go wrong with one of Elvis’ margaritas or a classic rum punch.
For a daytime beach bar, don’t miss the beloved Sunshine Shack on Rendezvous Bay where owner, Garvey, is slow cooking ribs, chicken, and fish on the beach. Embrace island time here and spend the day lazing in the sea with a cold Carib while lunch gets cooked up.
Take in live music at The Dune Preserve
Music lovers will fawn over Anguilla’s music scene. With a population of merely 14,000, the amount of musical talent on the island is astonishing, with a host of bands and solo artists playing at restaurants, beach bars and hotels across the island. The Dune Preserve, founded by island music legend Bankie Banx, offers live music in a setting that’s unlike any other.
Using remnants of washed-up driftwood and pieces from old boats, “The Dune” was started in 1994 and has maintained its draw, with scheduled music nights during the week. If you visit Anguilla in the spring, you can attend Moonsplash, a multi-day music festival under the full moon.
Sample local BBQ at Ken’s Pork
Driving through the island’s capital, you’ll see a primary school with hand-painted images of the island’s national symbols which include Anguilla’s national dish: rice and peas. There’s no better way to enjoy this combo than served with classic Anguillian BBQ at a local outpost, the way it’s been done for decades.
Head to Ken’s Pork in the Valley for a taste of island favorites: ribs, chicken or a combo served up with your choice of rice and peas, johnnycakes (cornmeal flatbread) and other island accouterments.
Sail at sunset on a traditional West Indian sloop
Tradition Sailing Charters swiftly became one of Anguilla’s most treasured experiences after its island debut, bringing an authentic Caribbean sailing experience to Anguilla's shores. A classic West Indian sloop, Tradition was handcrafted in Carriacou in the late 1970s and was built for sail trading through the Caribbean, running cargo through the region.
She lives a more peaceful life now, cutting through the sea in Anguilla with stunning excursions that capture a bygone era. Enjoy a morning mimosa while sailing out on a lobster lunch excursion or sip a handcrafted rum punch while watching the sun go down over the Caribbean.
Anguilla is on our 2022 Best of Travel list. For more stories from some of the world’s most exciting destinations click here.
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