When I need to get away for some relaxation, I always head to Anguilla. I’ve been there more than 30 times and I’ve never been disappointed in getting the decompression for which I’ve come. Of all the islands in the Caribbean, Anguilla (part of the British West Indies) has the most beautiful beaches. It also has a wide range of hotels and villa rentals—from the humble to palatial—and more importantly, a population of happy, friendly and courteous locals who will make your stay absolutely stressless.
For the quickest and best way to arrive in comfort and price, fly into SXM (Saint Martin) and take the ferry directly from the airport to Anguilla. For a little bit of the French Caribbean, you can take a taxi from SXM to Marigot harbor and take a different ferry from there. This is the French side of the island it holds some great shopping and genuine Parisian pharmacies where you can get sun protection products not available in the US and generally all things French. In the good news-bad news department, the ferry across to Anguilla is not as nice as the ferry from the SXM airport, but it runs every half-hour and is dirt cheap.
When to go
Right now! It’s officially low season and airfares/hotels are low, and there are no Christmas crowds. The weather is always perfect outside of rainy season—August through October—when many places are closed.
Where to eat
The spectrum of island cuisine is as wide as that of accommodation options. From roadside grills serving up chicken and ribs to the most inventive top-tier Japanese creations, the food is always great at any level you choose.
Here are a few of my food recommendations:
1. Blanchard’s Beach Shack
Blanchard’s has had its more formal (and excellent) restaurant on Meads Bay since 1994, it opened the beach shack about five years ago. Both are directly on the beach, and although the shack has a number of outdoor tables shaded by trees, I prefer to take my food directly to the sand and eat at my lounge. The food is truly fantastic; the blackened mahi BLT, street tacos and the burgers are my favorites. The salads are virtually infinite as you choose the lettuce; add-ons like chicken, warm goat cheese and sashimi tuna; and then your dressing. So good—and even better with your toes in the sand and views of the emerald blue sea.
2. Straw Hat
One of my favorites because it’s upscale but still local and not fussy. It’s also on Meads Bay and in fact part of the Frangipani Beach Resort, which is a small but luxurious place with 19 rooms, no two of which are alike. The outdoor patio of the restaurant is where you want to dine and the menu has curried goat sliders (me love), red snapper and NY strip steaks—so everyone will find something to enjoy.
3. Tokyo Bay
Chef Joe is an absolute food genius who invents some of the greatest sushi dishes you’ll ever have. I follow him on Instagram (_chefjoejitsu_) just to marvel at the beautiful new creations he shares with his posts. This is a chef that dives for his ingredients and makes his own caviar for garnishing the plates he prepares. Honestly all the accolades you can imagine still understate the magnificence of what is presented here. If Nobu came to eat here he would commit harakari; that’s how good it is. The best Japanese on Earth served on the best island on earth: a spectacular pairing.
4. Trattoria Tramanto
A great Italian spot with a beautiful beachfront location on the very southern tip of the island. It’s great for lunch, and for après lunch you can swim or take a power snooze on the comfy lounges under the palms. Evenings are wonderful as well, with views across the water to the twinkling lights of Saint Martin. The salads are great, and the pastas and seafood fantastic. Try the veal; it’s the best in the city. Sorry: There’s no veal, but I am compelled to use that Godfather line in all Italian restaurant reviews. Seriously, the panini is the best on the island.
Where to stay
Here are a few of my recommendations regarding where to stay:
1. CuisinArt Golf Resort & Spa
Generally I recommend CuisinArt Golf Resort & Spa to first-timers. It’s large enough to have everything you’ll want including an amazing spa and Tokyo Bay (see above)! The rooms are large, the bathrooms are beautiful and most of the rooms are directly facing the sea. It also has the only golf course on the island and takes great pride in growing on site most of the vegetables served at its restaurants.
2. Carimar Beach Club
If you’re more value-oriented as I indeed am, I’d suggest the Carimar Beach Club located on Meads Bay. It’s humble but clean and inexpensive, and it’s midway between the two most expensive hotels on the island: the very south-Miami-Beach Viceroy Anguilla and the newly refurbished, top-shelf Malliouhana. At Carimar, you can walk the beach and swim in the same crystal-clear water for a fraction of what you’ll pay at those two.
3. Anguilla Great House
On each trip to Anguilla you’ll want to go more local, and Carimar is a good transition, but for the full-on local experience, the Anguilla Great House on Rendevous Bay is the best place you’ve never heard of. I stay here a lot because they’ve got clean, air-conditioned rooms with Wi-Fi and TV at the lowest prices on the island, and besides sleep and breakfast, I‘m off to a different place every day. Nearly all the hotels and restaurants will let you use their beaches if you eat there. I also meet the most interesting people from all over the world that come here, and the staff is just so nice and helpful.
The beaches of Anguilla are the best in the world, and you should spend time at a hotel beach with comfy chaise lounges and umbrellas, full food and drink service, and an excellent watersports facility including Hobie Cats, paddleboards and kayaks. Take daytrips to secluded beaches where you may run into other people who will likely be just strolling by. At some beaches you may see a few horseback-riders splashing through the seaside, and that’s it. In fact, at Seaside Stables you can join a small group of riders and a guide and ride along a beach or through the water, which the horses love.
Here are my thoughts on a few Anguilla beaches:
1. Upper Shoal Bay
The most beautiful beach on the island is Upper Shoal Bay. It has the whitest sand, a sea of the bluest blues with a close-in reef for excellent snorkeling, and a few nice informal places to grab a bite—and no hotels.
2. Meads Bay
Meads Bay is larger and home to more hotels but has no reef.
3. The beach at Cap Jaluca
The beach at the very expensive Cap Jaluca is wonderful, and the secret is you don’t have to stay at the hotel to use the beach. There’s a parking area close to the southern end of the beach where you can park. From there, you can walk right over to the beach, where there’s a place to rent a Hobie or kayak if you want.
4. Rendezvous Bay
Rendezvous Bay is very secluded and a great place to bring your umbrella and watch the pelicans fly over in formation or the terns divebombing for baitfish.
Of course you may feel the need to get physical to justify all the massages and pampering you‘ll get at the spa and Anguilla Watersports has a great program of ocean activities including stand-up paddleboarding, kayaking and windsurfing. I opted for their eight-hour “Zero to Hero” kitesurfing lessons. My instructor Miquel, who I highly recommend, is certified and patient because this is the most difficult sport I have ever tried. The first day was spent on the beach for a three-hour lesson in kite control. It doesn’t require much strength, but rather finesse and understanding of the kite controls that enable you to position the kite precisely where you want it in the sky. The next day was spent in the water being dragged by the kite and learning to control it with one hand, with the other hand free to manage the board. By the afternoon of the second day I had learned to put it all together and was able to take off downwind. The wind conditions and numerous beaches in Anguilla make this an ideal spot to learn. If you’re an experienced kitesurfer, there will always be a great beach with ideal wind.
I never tire of Anguilla. Things are always changing, so there are always new restaurants and hotels. The good news is that new owners take over old sites so that the net growth of properties is modest, and the good-natured local vibe still permeates the island. And one last tip: When you rent a car, be advised that they drive on the British side of the road—but half the rental cars have steering on the right side and half have them on the American, left side. Don’t worry about getting used to it; you’ll quickly adjust and all the roads are slow-speed driving. Your problem will be that when you get home and thinking about what a great time you had in Anguilla, you might just find yourself driving on the left—island-style.
For more on Anguilla, visit ivisitanguilla.com.
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Editorial Note: The editorial content on this page is not provided by any bank, credit card issuer, airlines or hotel chain, and has not been reviewed, approved or otherwise endorsed by any of these entities.