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Updated: Apr 9

Anguilla (pronounced An-gwilla)

Anguilla is a small, mostly flat 35-square-mile island. There are about 16,000 residents here. The island's small population and tight-knit community contribute to its overall safety. It has an extremely low crime rate compared to many other Caribbean destinations.

Like the USVIs and the BVIS, there are plenty of abandoned and damaged buildings from Hurricane Irma in 2017 and the effects of the pandemic travel ban.

However, I just read recently that Anguilla made 32 million dollars last year from its Anguilla ownership of .ai (its assigned domain name like .ca for Canada). Given the surge in companies seeking internet addresses for artificial intelligence (A.I.) — such as Elon Musk's website — Anguilla has experienced a substantial rise in demand for domain names.

Great for them!

Ah....the beaches!


Anguilla is a lot like Ken from the Barbie movie.

Ken: "Yeah, because actually, my job... it's just beach."
Barbie: "And what a great job you do at beach!"

Anguilla does beach (and beach bars and beach bar characters) better than any island we've been to yet!

Road Bay/Sandy Ground

Sandy Ground looking out at Road Bay

We cleared into Anguilla at Road Bay. It is the only bay we are allowed to anchor in for free. Anguilla charges boats, based on length, a cruising permit fee to anchor in other bays. For us, a 40 foot boot, the fee is $86 a day. The high cost isn't even the worst part. There is no overnight anchoring allowed so the boat has to be moved back to Road Bay by 7pm.

Bankie Banx (you'll learn about him later) is quite a pirate and told us to just anchor anyway, permit be damned, they have no boat to enforce it. That's easy for him, a local legend, to say. We're dumb, white Americans and weren't willing to risk the $3000 fine and 6 months in jail.

We opted for the alternative of staying put in Road Bay and renting a car at $35 per day to explore the island at our own pace. Plus Dave got a cool Anguillan driver's license out of the deal. Dave pointed out that it had the wrong year on it and the guy was like. "So what, doesn't matter." OK. Which does sum up the laid back feel of Anguilla.

Sandy Ground at Road Bay is known for its beautiful sandy beach. The beach features soft, powdery sand and clear turquoise waters. This was our home for 2 weeks and we enjoyed it every day.

The atmosphere is often festive, especially when small cruise ships anchor out and during the evenings when there is live entertainment everywhere.. The music lasts until about 3am and then the roosters start crowing at 4am. Good thing we can sleep through anything.

Anguilla is our Happy Place! Ignore my bad boat hair!

There are a variety of beach bars and local eateries offering delicious Caribbean cuisine, Italian food, and refreshing tropical drinks.

We loved the Criss Conch Shack for fresh conch at a reasonable price! It's a real family operation. Dad and the son fish for conch all day and Mom runs the restaurant. We ate here a couple times because it was too good to only have once!

Criss Conch Shack

Dave chatting up the Conch fishermen.

Elvis' Beach Bar

Elvis' beach bar in Sandy Ground holds a special place in our hearts. Prior to heading back to our boat each evening, it became customary for us to drop by for a nightcap with Elvis himself! Soft spoken Elvis is a legend. We happened to be there for his 60th birthday celebration, which was akin to Diddy's white party.

We loved the whole staff-Carlson, Elvis' daughter Tammy, and Charmaine.

Brett and Charmaine

Brett, Elvis' co-owner is also an interesting character. He started off sitting quietly, sipping water each evening on his bar stool. But halfway through our visit, we saw a man dancing on the back of a boat waving his shirt in the air and were shocked to realize it was Brett. After that, we saw a different side of him, much more rambunctious and full of rum! On our last night, Brett loaded us up with lots of Elvis swag! Thank you!

Besides the great staff, we met other such fun people there like Coop and Judy from Niagara, lots of super nice tourists, fellow sailors, a few pilots, Mo and Cindy from Sint Marteen, and bunches of locals including two artists and one certifiably crazy lady. Anguilla is small and we ran into the same people everywhere we went.

Dave kept bugging Elvis about where he got his cool scarf. On the last night, Elvis took it off and threw it at him to keep. I guess just like the real Elvis used to do.

Our time there was filled with laughter and fun conversations. We also engaged in some friendly competition playing Elvis' beach games such as giant Jenga, giant Connect Four, Cornhole, and the Hook and Ring game. Which Elvis can make every time, even blindfolded! We witnessed it.

Elvis' is famous for its Goatchos (nachos with local goat meat). We enjoyed the very delicious shrimp tacos and their generous helpings of french fries.

The cold beers, stunning sunset views, and great conversations at the One Love Boat Bar (the bar is a boat) made for unforgettable moments.

Watch this video to get a feel for the place.

Shoal Bay East

Shoal Bay East

Picture-perfect doesn't even begin to describe Shoal Bay East. With its powdery white sand stretching for miles and waters so clear you can count the grains beneath your toes, it's like stepping into a postcard. Snorkeling here is good if the conditions are right. The waves get pretty big here and can rake you over the coral if you're not careful.

We watched a couple get taken down by two huge waves. The poor husband lost his sunglasses. His attempts to retrieve them were unsuccessful. I did feel bad for them but watching those waves knock them over was pretty funny.

Ray painted his umbrellas which is kind of weird .

Ray of Ray Da Man Beach Chairs will be the first to greet you in the parking lot. He wants to supply you with chairs and an umbrella for $15. Come later in the day (around 2) and the price drops to $10. You need the umbrella too because there is not much shade on this gorgeous beach.

There are a bunch of great beach bars here. We enjoyed cocktails at Olas Tacos a few times while we were sitting on our beach chairs. They have insanely strong Rum Punches.

We spent a lazy Saturday at Madeariman enjoying some great live music. We got a real treat when Elvis showed up and the band invited him up to sing some Bob Marley.

Shoal Bay is about a 2 mile long beach. We walked it several times and at the very far end of it, we were rewarded with a cold beer at Gwen's Reggae Grill.

Maundays Bay

Maundays Bay

Maundays Bay has a crescent-shaped beach, adorned with soft, white sand and fringed by swaying palm trees. The brilliant blue waters provide an ideal setting for a relaxed swim or a romantic walk.

Maundays Bay lies within the grounds of the luxurious Belmond Cap Jaluca Hotel. While it may seem exclusive, all beaches in Anguilla are public.

The guard at the gate warmly welcomed us and guided us to parking. As we arrived, we were offered a tour of the property and its three restaurants via golf cart.

Belmond Cap Jaluca Hotel

For a mere $3000 a night, you can rent a one bedroom suite with your own private plunge pool.

There are "bar" stations every 100 feet on the beach so the wait staff doesn't have far to walk to deliver a rum punch to a sunbather.

Dave and I leisurely strolled along the shoreline to reach the Cap Shack beach bar, where we indulged in the island's priciest bottles of Carib beer at $15 a pop! We don't recommend you patron this establishment unless you are one of the people burning three grand a night on a hotel room!

Cap Shack Beach Bar

Anguilla Arch

On the way to Maundays Bay, we took a slight detour to explore the Anguilla Arch. The shoreline with the cliffs and the color of the water all play together to make this scenic stop worth it! You can come by boat and snorkel around the arch too.

Dave is King of the Arch

We did not have any trouble finding The Arch. The bumpy, dirt road is well marked with these signs.

Meads Bay

With its vibrant turquoise waters and a lively atmosphere, Meads Bay is the place to see and be seen. The beach is dotted with upscale beach bars, hotels, and restaurants.. It has a sports area where you can rent a Hobie Cat, SUPs, and those crazy bicycle pontoon boat things.

Meads Bay

We loved the view and the comfy outdoor couches at Leon's.

There is no shortage of dining options along Mead Bay, and one of our memorable experiences was dining at Blanchard's. This charming establishment came highly recommended by a delightful Canadian couple whom we encountered repeatedly during our time on the island. Regrettably, their names escape us now (If you happen to read this, reach out!)

Rendezvous Bay

Rendezvous Bay

In our view, Rendezvous Bay stands out as the premier beach on the island. If you relish leisurely strolls by the shore, Rendezvous Bay is the place to be. Extending over two miles, this vast expanse of sand offers ample room to unwind and bask in the sunlight.

This bay is a favorite anchorage for mega yachts. We observed the crew of one such yacht setting up a dedicated sunbathing area for their affluent passengers, complete with a private bar and bartender (whose name tag subtly reminded us of her role as hired staff, in case there was any confusion).

Hard to see the rich people's set up here. I didn't want to be too obvious snapping their picture.

The Dunes Preserve

The Dunes is mulit-tiered with lots of cool spaces.

What makes Rendezvous Bay so special is a beach bar called The Dunes Preserve owned by quite a character, Bankie Banx.

Bankie is a renowned musician from Anguilla, Born as Clement Ashley Banks, he adopted the stage name "Bankie Banx" for his musical career. Bankie is primarily known for his contributions to reggae music, although his style encompasses elements of various genres, including calypso and folk.

Banx gained international recognition for his unique sound and soulful performances.

Throughout his career, Bankie has released numerous albums and singles, earning a dedicated fanbase and critical acclaim for his authentic and heartfelt music. He remains an influential figure in Caribbean music, continuing to perform and inspire audiences worldwide.

The Dunes Preserve originally began as a beach bar established by Bankie's parents. Upon his return, he took the reins and expanded its scope. Following its devastation by Hurricane Irma in 2017, he undertook the task of rebuilding it from the ground up.

The Dune Preserve is not just a typical beach bar; it's a rustic and charming establishment built from salvaged materials, driftwood, and other found objects. The bar has a unique, eclectic vibe that reflects Bankie Banx's artistic sensibilities and love for the natural beauty of Anguilla.

On our first visit, we were lucky enough to meet Bankie and his nephew Lateef, the bartender. They were busy putting finishing touches on the place for the upcoming festival, Moonsplash.

The Dune Preserve is not only a popular spot for locals and tourists to unwind and enjoy tropical drinks but also a hub for live music. Sunday School on Sundays at 4 is the place to be when Bankie and friends take the stage.

We were only planning to stay on Anguilla for a week but when we found out that Bankie's Reggae Festival Moonsplash was the following weekend, we added on an extra week so we could attend.

Moonsplash 2024

Bankie played all three days in different bands.

Moonsplash is a must-attend event for music enthusiasts. This vibrant festival lasting 2 nights and one afternoon, is held annually. It brings together local and international artists to celebrate Caribbean culture through music, dance, and festivities. Both Jimmy Buffet and Bob Dylan have been regular performers at it.

No money is used. We had to preload our Bankie Dune Bucks card.

We had a fantastic time at the weekend events, reconnecting with many familiar faces from the island and making plenty of new acquaintances as well.

The music was incredible. We especially liked Protege. He put on a great show. Bankie's son Olaide Banks was great too. The tribute band to Jimmy Buffet The Smoky Reefers, featuring Bankie was very fun. All the acts were great and thanks to the band Drak Shakespeare I have had their Chocolate and Vanilla song stuck in my head for the past two weeks!

Wasting Away Again in Margartville

During our time in Anguilla, Dave and I became the living embodiment of Jimmy Buffett's iconic song "Margaritaville". We found ourselves in a perpetual state of island bliss, relaxing and indulging.

Strangers became friends over shared stories and salt-rimmed glasses. We enjoyed the island music and all Anguilla's lovely people- locals and visitors alike.

We are heading to St. Martin/Sint Maarten next, where we aim to enjoy ourselves responsibly and perhaps engage in healthier activities like hiking!

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David Althoff
David Althoff
Apr 04

Great post! As I am sitting here watching the pouring rain/sleet in Syracuse, seeing you two chillaxing gives me hope and I feel a little better. Keep the posts coming!

Diane Rhodes
Diane Rhodes
Apr 04
Replying to

Oh no. I do not miss the gray, rainy days of Upstate NY springs! You guys need to get your butts down here too!! Thanks for reading! :-) Miss you.

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