The Wanderlust Effect’s Guide to 24 Hours in Anguilla

By Shannon Kircher on 2nd June, 2017

Anguilla is the epitome of barefoot luxury, with its offering of laid-back fine dining, horseback island explorations and quite possibly the world’s best beaches.  Travel blogger Shannon Kircher, AKA The Wanderlust Effect shares her 24 guide of what to see, do and eat on this enchanting island.


Anguilla is a rather extraordinary island in that it manages to capture all things enchanting about the Caribbean while flying under the radar. For people that do know of it, it’s just that: a secret gem for those in the know. Unlike neighboring St. Barths that often evokes images of glamorous celeb-worthy beach escapes, a mention of forthcoming trip to Anguilla will often be met with, “where?” or, better yet, an assumption that you’ve butchered the pronunciation of Antigua.

16 miles long and 3 miles wide at its widest point, Anguilla’s shape resembles an eel, which is how it earned its moniker (‘Anguilla’ means ‘eel’ in Spanish and Italian). Good things come in small packages, or so the old adage goes, and this is undoubtedly true on this island in the British West Indies. Many hotel and restaurant owners on the island would describe Anguilla similarly; an island of barefoot luxury. It’s one of the Caribbean’s most exclusive islands, yet manages to balance luxe offerings with an unpretentious air.

I’m a bit biased since I get to call this island home, but I’ll shoot it to you straight: there’s a reason that Anguilla sees an astounding number of repeat visitors. Once you’ve discovered the island, you’ll be hard pressed to look for a vacay elsewhere (even day trippers fall into this camp, so don’t be surprised if 24 hours is enough to fall in love). Anguilla offers an impressive medley: spectacular beaches, a lively beach bar scene, and world-class dining complemented by exceptional musical talent. Thinking you can’t possibly experience it all in just 24 hours? I’ve got you covered for the ultimate island taster, with a few options depending on your travel style.

Morning | Island Exploration or a Seaside Ride


If you’re an early riser, take the time to explore the island before the sun is out in full force. If you’re arriving by boat from St. Martin, try to take one of the earliest public ferries over to maximize your time on Anguilla (public ferries depart every 45 minutes from Marigot on St. Martin’s French side). For the explorers in the bunch, Anguilla is relatively easy to see in a couple of hours. You’ll want to scope out some of the island’s most iconic beaches: Rendezvous Bay, Meads Bay and Shoal Bay. If you’re a history buff and want a quick primer on the island, head to Anguilla’s Heritage Museum, headed by Mr. Colville Petty, a historian who has curated the museum’s collection. If you’re the independent type, look at renting a car to explore at leisure (Gumbsie and Highway Rental Car are great locally operated agencies). For about $45/day + a temporary license fee, you’ll have wheels to get you around so you can go at your own pace. If driving on the left isn’t your cup of tea, taxi drivers on the island will be happy to set you up with an island tour and a healthy dose of island knowledge for those wanting cultural insights.

If island exploration isn’t a priority for you, opt for a memorable horseback riding experience on the beach. Tania at Seaside Stables offers morning beach rides before the sun is in full swing, for an incredible way to kick start your day. Enjoy a morning jaunt along Cove Bay for one of the island’s most romantic offerings.

Feeling peckish? Grab a morning bite and a cup of coffee at Geraud’s Bakery, the go-to bakery for locals, expats, and tourists alike.

Daytime | Lunch on the Beach


If Anguilla is famous for a single thing, it’s the beach scene. By late morning you’ll likely want yourself firmly planted on a sandy stretch somewhere taking in the island’s blissful beach vibes. Pick your lunch strategically so you can enjoy a stunning beach scene and a fabulous lunch. My two favorite beaches for lunch? Meads Bay or Rendezvous Bay; both long, beautiful crescents great for walking with serene waters for an afternoon dip.

Meads Bay is home to some of the island’s most exclusive hotels and restaurants, and makes a great place to set up for the day. Try Straw Hat Restaurant for a great menu, beach chairs, and wonderful beachside service. Their spicy fish sandwich is a favorite, and their bartenders are putting out wonderfully refreshing concoctions all day long. If you’re looking for something with a more European flair, head to Jacala on Meads Bay, where co-owners Jacques and Alain serve up fabulous French food that deserves to be celebrated with an afternoon bottle of rosé. Chairs are available for diners so you can easily move from lunch to beach for a relaxed afternoon.

If you want gorgeous views of St. Martin while basking, head to Rendezvous Bay where the picturesque shore provides views of mountainous St. Martin across the channel. The Sunshine Shack, smack dab in the middle of Rendezvous Bay, is a wonderful place to post up for a sunny afternoon. Garvey, the proprietor, serves up his famous ribs, chicken and fish in a toes-in-the-sand setting. Don’t forget to sign your name on the bar as proof that you spent the day there.

For more lunchtime dining, check out this full post on where to spend a perfect afternoon with equal parts delicious dining and gorgeous beach scene.

Early Evening for the Food Lover | Pre-Dinner Cocktails


Sunset Lounge at the Four Seasons

Generally speaking, Anguilla is an island slanted towards casual elegance, and many establishments embrace that philosophy (e.g. there’s no place on the island that you would ever have to wear a sport coat…. Or even closed-toed shoes for that matter). That being said, there are a few places to enjoy a more lavish side of the island, perfect for a more glamorous night on island after a beach-filled day.

If you’re ready in time for sunset, head to the Sunset Lounge at Four Seasons for a cocktail with a view. Formerly the Viceroy, Four Seasons has kept the beloved Sunset Lounge in place with an Asian-fusion menu plus great cocktails and live entertainment select nights of the week.

If you’d rather keep the shorts and flip flops scene going with a beautifully casual vibe, head down to Sandbar in Sandy Ground where you can sip on one of their signature Sandbar cocktails – essentially a frozen rum punch with a floater (how can you go wrong?) – while watching the sun set on the island’s main harbor.

Early Evening for the Sea Lover | Set Sail Aboard Tradition


{Phot credit: Vineyard Vines}

For those that prefer not to part with the ever-present draw of the Caribbean Sea, enjoy an alternative sunset experience aboard Tradition Sailing. Head down to Sandy Ground and you can’t miss the candy apple red West Indian sloop majestically resting in the harbor. Helmed by Captain Laurie Gumbs, Tradition offers a range of sailing excursions throughout the day, but their pièce de résistance is their sunset tapas cruise that allows guests to experience a serene evening at sea while the sun sets and stars begin to light up the night sky. Complete with a mouth-watering selection of tapas, a sparkling dose of bubbly and a selection of rums, it’s an idyllic evening enjoying a quintessentially Caribbean experience.

Evening | Dinner or an Appetizer Crawl


I recently shared a post on 24 hours in St. Barths where I discussed my affinity for self-guided appetizer crawls, and I would argue that a similar approach works beautifully in Anguilla. Anguilla’s dining scene is famed within the Caribbean, with a gastronomic tradition that belies its tiny size and rustic feel. Choosing just one restaurant can seem like an impossible task, so if you’re in the mood to bounce your way around the island scoping out a few restaurants and resorts, plus enjoying an app and a cocktail at each, here’s a rundown that will allow you to hotel and restaurant hop along gorgeous Meads Bay:

First off, if you followed my early evening advice above, you may have begun your night at the Sunset Lounge at the Four Seasons, which is the perfect place to kick start a foodie evening, and the most western point of this crawl. Split a sushi roll and enjoy a handcrafted cocktail while taking in the evening vibes. From there, head just slightly east on Meads Bay to Straw Hat Restaurant at Frangipani Beach Resort, where their tuna flatbread has earned a spot as my favorite appetizer on the island (bold statement, but accurate). Pair with a classic Caribbean cocktail, and enjoy the beachfront bar scene. If you want a dose of glam, head to Malliouhana on the eastern point of Meads Bay, where the highly Instagrammable lobby will draw you in for a few moments. Their bar brings some old world charm, and I generally find their appetizers to be the star of their offerings.

Still on the move and hungry for more?

Hop in a cab and head from Meads Bay to Sandy Ground (about a 15-minute drive), where you can pop into a number of fabulous restaurants right along the beachfront, followed by a visit to some of the island’s most popular beach bars.

Late Night | Beach Bar Hopping in Sandy Ground


Elvis’ Beach Bar

Anguilla may not be known as the nightlife capital of the Caribbean, but Sandy Ground provides the perfect late night bar crawl opportunity after dinner, complete with live music on select nights. Elvis’ Beach Bar and The Pumphouse are go-to spots for a post-dinner cocktail, and it’s worth experiencing both for two different scenes. Thursdays are a great night to be out in Sandy Ground, where you can dance to live tunes by the Musical Brothers beginning at around 9PM, but a visit to Sandy Ground any night of the week will provide the perfect beachy finale to your day on the island.

Success! If you’ve actually made it through that jam-packed day, you’ve experienced a solid dose of the charm that draws visitors to Anguilla year after year. For those that have been to the island, what’s your perfect day in Anguilla?


Shannon Kircher is the Founder + Editor of The Wanderlust Effect, a travel blog focused on experiential travel and cultural experiences around the globe. Born and raised in California, she now lives on the Caribbean island of Anguilla where she and her husband operate Frangipani Beach Resort, and dedicates around two months a year to international jet-setting.  You can follow her adventures on Instagram at @lavidashannon