Destination GuideTravel


By 10.06.16. No Comments

Let’s be honest here.  Drop us off at any island in the Caribbean, and we would definitely not complain.  Each island shares similar traits: turqoise ocean, abounding sunshine, and a slow pace of life that will calm your nerves and soothe your senses in the most refreshing way.  Not to mention fresh seafood, friendly locals and ever-flowing rum.  But trust us when we say that the tiny island of Anguilla (only sixteen miles long and three miles wide) is a Caribbean gem.  There are no all-inclusive mega-hotels, no chain restaurants, and no casinos, cruise ship harbors or duty-free shops.  What you will find in the place of what would otherwise be paved with commercialization are 33 pristine beaches, boutique properties, dozens of world-class, family owned restaurants and the clearest water you’ve ever seen.  We’ve yet to find anyone who has been and said they wouldn’t go back. Visit this island, and you won’t want to leave.



Cap Juluca
Maundays Bay
Anguilla, BWI

Cap Juluca is a breathtaking resort that has been a fixture on the island since it opened in 1988.  The property features stunning Morrocan architecture and design, with guests staying in rooms, villas and suits that sprawl the span of the entire beach of Maundays Bay, so there isnt’ a tall building in site.  Every single room sits on the beach.  At night, you will fall asleep to the sound of the ocean waves right outside your door.  The property does have a pool, but the beach is the main attraction at this resort.  Guests have their own beach chairs right outside their rooms, with beach attendants who will be at your beckon call throughout the day.  Just drop the flag on your umbrella and they’ll come to you.  In the afternoon, beach attendants will deliver complimentary chilled towels and sorbet.  The staff is extremely friendly and accommodating… you won’t have to lift a finger while staying at Cap Juluca.

Four Seasons Anguilla
Meads Bay
Anguilla, BWI

This sprawling luxury resort is located on the end of Meads Bay, one of the island’s best beaches, and has breathtaking views.  The resort boasts a spa (one of the best on the island), three pools, a sports pavilion, four restaurants and of course, plenty of beach.  The hotel decor was designed and styled by Kelly Wearstler, and features her iconic mix of natural materials like driftwood, marble and animal-skin textiles, covering the property in a blanket of neutral elements.  The only bright caribbean colors you’ll find here are on the caftans sold in the resort’s high-end boutique.  But Wearstler’s neutral pallet compliments the resort’s natural surroundings perfectly.  The standout features of this property are numerous… but our favorites are the views, the spa and the incredibly serene Sunset Pool.

Meads Bay
Anguilla, BWI

Situated on top of a bluff at the end of Meads Bay beach, Malliouhana is a vibrant Caribbean hotel with a Euro-chic atmosphere, spanning 25 acres of lush, impecabally landscaped grounds.  Actually Anguilla’s first luxury hotel property, Malliouhana put Anguilla on the jet-set radar in the early 1980’s when it was opened by an England couple.  But in 2011, the resort closed and remained vacant for several years, until it was bought by Auberge Resorts and renovated and updated into a modern oasis that still preserves the original, retro feel of the hotel. As you arrive onto the property, you’ll instantly be charmed by the facade with its ivy-covered white exterior and  turquoise striped awning.  The main house features a breathtaking view of the Caribbean Sea, as seen in the photo above, and a TWO-TIERED infinity pool with the chicest black and white striped cabanas and orange ruffle umbrellas.  Basically chic AF pool goals.  Guest rooms are bright and cheery just as you imagine Caribbean vibes to be, with four-poster beds, private terraces and impeccable views.  Combine all of that with access to multiple beaches (one being Meads Bay which is one of Anguilla’s best), a spa and a delicous restaurant, and you’ve got a winner in our opinion.

Turtle’s Nest Beach Resort
Meads Bay
Anguilla, BWI

Renting a condo at Turtle’s Nest is a great option if you’re looking for more affordable accommodations.  You can rent anything from a studio to a three bedroom condo, all which are fully furnished and feature a kitchen, ocean-front patio, wi-fi, tv’s and washer and dryers. Daily housekeeping services are provided as well as towels for the beach and pool.  You will have the comforts of a condo with the amenities of a hotel.  Not to mention its location on Meads Bay can’t be beat, sandwiched between Malliouhana and Four Seasons, two of the island’s top resorts.  Walk to Malliouhana for breakfast before spending your day at the beach, and at sunset, walk over to Viceroy for cocktails at their Sunset Lounge.  You’ll also be within a few steps from other Meads Bay restaurants like Straw Hat, Jacala and Blanchards Beach Shack.  


Blanchards Restaurant and Blanchards Beach Shack
Meads Bay, Anguilla
Anguilla, BWI

Bob and Melinda Blanchard ran several successful businesses in Vermont when one day, after they’d raised their son, they sold everything and moved to Anguilla to start a new venture.  They opened Blanchards Restaurant on the beach of Meads Bay in 1994, which quickly became known as one of the best restaurants for dinner in the Caribbean, and it still holds that title today.  Years later, they opened Blanchards Beach Shack, a laid-back place to grab lunch and a cold drink.  It’s located right on Meads Bay beach, so you can walk there if you’re staying at Malliouhana, Viceroy or Turtle’s Nest.  It’s super casual, so wearing nothing but your bathing suit is totally acceptable.  The menu has anything you could want, from sandwiches and salads to burgers and rice bowls. Cool off with the frozen mojito!

Sunset in Anguilla.

Crocus Bay
Anguilla, BWI

da’Vida is a beautiful open-air, fine-dining restaurant located on the beach in Crocus Bay.  The menu has an Asian influence and offers dishes from lamb to scallops to lobster spring rolls.  The atmosphere is relaxed and breezy and the view is incredible.  Go early and have a few cocktails and watch the sun set behind the sailboats before dinner.

Dolce Vita
Sandy Ground Village
Anguilla, BWI

For a delicious Italian meal and some great wine right on the beach, go to Dolce Vita.  Restaurateur Abbi Ibrahim and chef Christopher Bacchiega, the duo behind this charming restaurant, met in Italy while they were both working at a Michelin starred restaurant.  Years later, they are running one of the best restaurants in Anguilla. You can’t go wrong ordering here.  Everything is delicious, from the fish to their homemade pastas.  And if you’re in the mood for something other than seafood, order La Lasagna di Dolce Vita and thank us later.  (Tip: Before dinner, walk down the beach to Elvis’ Beach Bar for a rum punch and meet the famous Elvis.)

West End
Anguilla, BWI
1.264. 498.1616

Picante is the answer to all your Mexican food cravings while you’re in Anguilla. This taqueria is incredibly delicious and has an adorable atmosphere with insanely good guacamole, margaritas and if you only take away one thing from this guide, let it be to ORDER THE PICANTE FISH TACOS.  Owners Chloe and Theron were visiting the island years ago when one night they were craving Mexican food but realized there was no Mexican restaurant on the island. So what did they do? They went home to California, packed all of their belongings, moved to Anguilla and opened Picante. It has been a favorite of visitors and locals ever since. 

Maundays Bay
Anguilla, BWI

Talk about a breathtaking dinner view.  Pimms is a fine dining restaurant located at Cap Juluca resort, and is probably the most serene, romantic restaurant on the island.  Everything from the food and presentation to the service and ambiance is on point.  Feast on a delectable meal while sitting feet away from the ocean.  This is a perfect place to celebrate a special occasion like a birthday or anniversary, or the simple fact that you want to have a great meal in one of the best atmospheres on the island.  

The Restaurant at Malliouhana
Meads Bay
Anguilla, BWI

Malliouhana’s restaurant is an excellent place for breakfast or dinner.  Their breakfast is one of the best on the island with a selection of healthy options like fresh green juice and egg-white omelets and more indulgent options like toasted coconut pancakes.  Dinner here is also an excellent option.  You can’t beat the view from on top of the bluff at Malliouhana.  Go early enough to watch the sunset and enjoy.

Smokey’s at the Cove
Cove Bay
Anguilla, BWI

Smokey’s is the place to go for a casual lunch or dinner.  The fish sandwiches are delicious and some say their rum punch is the best on the island.  It’s located right on the beach and offers beach chairs and umbrellas if you want to relax after your meal, or play a game of corn-hole in the sand.

Sandy Ground
Anguilla, BWI

This restaurant may not have an ocean view, but have you ever eaten a five-star dinner in a tree house?  Located in Sandy Ground on the side of a hill, Veya is tucked away in the middle of lush, Caribbean jungle.  Chef Carrie Bogar and her husband Jerry, both originally from Pennsylvania, moved to Anguilla and opened Veya in 2007 (seeing a trend here?) and it has earned rave reviews ever since.  It’s an upscale spot that should definitely be on your list for a nice dinner out on the island.  


Elvis’ Beach Bar
Sandy Ground Village
Anguilla, B.W.I

Located on the beach in Sandy Ground, this boat-turned-beach bar is a fun, one of a kind place that you need to visit while you’re on the island.  Elvis himself is usually behind the bar and will make you a mean rum punch. Elvis’ also offers corn hole, beach volleyball, a giant screen TV and hammocks to relax in.  It’s a perfect place to stop by for a rum punch before you have dinner at one of the restaurants on Sandy Ground. 

Dune Preserve
Rendezvous Bay
Anguilla, British West Indies

If you’re a fan of reggae music, you should definitely hit up the Dune Preserve on Rendezvous Bay, owned by Caribbean reggae star Bankie Banx.  The bar is an open-air wooden structure right on the beach, with a super chill, Rastafarian vibe.  If you’re lucky, Bankie himself might be playing. 

The Pumphouse
Sandy Ground,
Anguilla, BWI

The Pumphouse is the place to go on Thursday nights for live music and dancing. It’s a favorite of visitors (even celebs!) and locals alike, and never fails to be a good time.  It’s located in Sandy Ground, so make a night of it and start at Elvis’ Beach bar for a rum punch, then walk down the beach to dinner at Dolce Vita, then head to The Pumphouse and dance off all that pasta. 

Sunset Lounge at the Four Seasons
Meads Bay
Anguilla, BWI

The Sunset Lounge at the Four Seasons is one of the best spots on the island to watch the sunset.  Its located next to one of the resort’s infinity pools with an amazing view of the ocean. Go a little before sunset, get a cozy seat, and order cocktails and some sushi or small plates before you head off to dinner.  This also makes a fun place to stop by after dinner for live music and a nightcap. 


The Boutique at Four Seasons

Your best shopping on the island will be found at the resorts. The Boutique at Four Seasons carries everything from colorful Missoni caftans and swimsuits to Edie Parker clutches and Jimmy Choo shoes.  It’s a great excuse to treat yourself if you “forgot” to bring something you need for the trip. 😉 

The Boutique at Malliouhana

The Boutique at Malliouhana carries a great selection of swimwear, beach bags, jewelry and resort wear, in addition to sundries lest you forget any items you may need.   


Natural Beauty of the Island
Anguilla is definitely an island where you can (and should!) venture off of your hotel property and do some exploring.  You can find breathtaking landscapes and views all over the island.  All of the island’s 33 beaches are public, and they’re worth checking out.  Our favorites are Meads Bay, Maundays Bay, Shoal Bay East and Little Bay.

Sunrises and Sunsets
While we always advocate for catching a sky show or two (they just never get old), Anguilla sunsets (and rises for you early birds) shouldn’t be missed.  There are countless places to watch a sunset on the island, but The Hollyday favs are the Sunset Lounge at Four Seasons, the the Sunset Bar at Malliouhana, da’Vida on Crocus Bay, and Sandy Ground.  Download the app Magic Hour, which tells you exactly when sunrise and sunset will be wherever you are.


Horseback riding through the ocean in Anguilla, BWI.

Kayak or Paddle Board to Little Bay

Little Bay is a small beach on the island that is best accessed by water from Crocus Bay.  Rent kayaks or paddle boards at da’Vida Bayside Grill in Crocus Bay, and paddle around the right side of Crocus Bay and you will come upon Little Bay (pictured above).  There is a small beach where you can park your kayak or paddle board and do some exploring. Little Bay is also said to have some of the best snorkeling.  Pro tip: pack a small cooler filled with cold drinks and take it with you on your kayak or paddle board so that you can spend a few hours relaxing on Little Bay.

An Afternoon at Scilly Cay

Scilly Cay is a small island in the bay of Island Harbour.  A local Anguillan family has turned the island into a daytime restaurant experience, complete with a delicious, fresh-off-the-grill entree, flowing rum punch, a bar and music (live on Sundays).  Walk out to the end of the dock at Island Harbour and wave… a boat will come get you and take you the short distance to Scilly Cay.

Horseback Ride on the Beach

Remember this post? Well, you can get the experience for yourself.  Have your hotel concierge call Anguillan local Zambezi for a horseback ride on Maundays Bay, or arrange a ride with Seaside Stables.

Charter a Sailboat

Chartering a sailboat for a day is a great way to see the whole island. Have the boat take you on a day trip to Sandy Island or Prickly Pear, or charter a sunset cruise. Chocolat is a great option, which you can read more about here.


How to Get There

Getting to this little island is half the fun.  You will fly from the U.S. into St. Maarten (SXM). From there, you will take a short boat ride to Anguilla. Your hotel, condo or villa owner will gladly help you make the arrangements, but you basically have 2 options: either go on a chartered sea shuttle or take the public ferry. The fee for a shared sea shuttle is about $70/person, one way. (We recommend Funtime Charters or Calypso Charters.) Your boat captain will meet you in the arrivals area of the St. Maarten airport, help you with your luggage and take you to the pier where you will board your boat. You’ll be in Anguilla in about 20 minutes, and they serve complimentary beers, rum punch and soft drinks on the ride over. (Booking a spot on a chartered sea shuttle should be done in advance.)  The other option is taking the ferry, which will depart from Marigot in St. Martin.  It’s cheaper (around $30/person) and runs every 45 minutes, but you’ll have to take about a $20 cab ride from the airport to the port.  Whichever way you choose, plan some extra time in between your arrival in St. Maarten and your boat departure, and make a pit stop at the Sunset Bar and Grill, right next to the St. Maarten airport.  This world-famous spot is located right between the airport runway and the ocean. Have a fish sandwich and a cold drink (much needed after a long flight) and watch the planes fly in and out right over the water. This is a great way to start off your trip, and will be an experience you won’t forget.  

When to Go

High-season on the island is from December until March.  While this is a popular time to go (cooler temps and holiday travelers) and often an exciting time on the island, it’s also the most crowded and expensive.  Making the trip during the low-season, which lasts from April until the end of August, means fewer crowds and lower prices.  Off-season (a.k.a. hurricane season) runs from the end of August until November, and many of the restaurants close for this period.  Minus hurricane weather, really any time on the island is paradise.  We recommend going anytime between December and August. 

How to Get Around

Once you’re on the island, most of the resorts will provide transportation for their guests or will arrange for a taxi to pick you up and take you to your destination. Some visitors prefer renting a car, which is not difficult to do.  The island is easy to navigate and having your own car makes exploring easier.  Tell your hotel concierge you would like to rent a car and they will line it up for you.  You can read more about renting a car in Anguilla here navigating the island here

Zika Virus

Local transmission of the Zika virus has been reported in Anguilla, meaning mosquitos carrying the virus are present on the island. Women who are pregnant or planning to become pregnant should not travel to Anguilla. Zika can also be transferred sexually. Click here to read the CDC guidelines on how long you should wait to become pregnant after traveling to Anguilla. For general information on the Zika virus in Anguilla, click here.

Departure Tax

When leaving the island, all tourists must pay a $28 departure tax (per person) in cash, which you will pay before going through customs at the boat dock in Blowing Point.

Nori Evoy is a local and an expert on all things Anguilla, and writes all about the island on her website,  It’s a great resource for any questions you might have or to get more information when planning your visit.  Sign up for her monthly newsletter here to stay up-to-date on all the hotels, restaurants and things to do.