Anguilla’s Sandy Island is an ideal lunch spot.

Sharon Mathews-Stevens

Back onboard we headed for bed right away because tomorrow was Anguilla, one of the week’s longest passages.

From a distance Anguilla seemed relatively uninteresting, but once we rounded Anguillita, a tiny cay off Anguilla’s west end, we glided past gorgeous cliffs of red rock, a smattering of luxury resorts populating irresistible ivory beaches just demanding further investigation. 

Our passage from Grand Case was nothing short of delightful. Think a lovely beam reach through following seas with three or four jibes before rounding Anguillita and hardening sails for an exhilarating close reach up to Road Bay. It was the first real romp of the trip with flat water and 20 knots true.  Shaun and his wife Cait had the helm, calling out updates in excitement.

Shaun called the boat speed “Eight knots! Eight-and-a-half.”

Marigot bustles night and day.

Sharon Mathews-Stevens

Cait joined in. “Nine! Nine point six!”

Anguilla does levy a fairly heavy fee for a cruising permit and it’s required if you want to explore some of that island’s smaller cays but those gorgeous waypoints Prickly Pear Cays and Sandy Island do make it worth the cost and you don’t have to pay for the permit if you want to anchor at Road Bay or Crocus Bay.

I wanted to introduce my crew to Sandy Island, a wave-swept oasis roughly a nautical mile out from the Road Bay anchorage, so opted for a one-day permit. Once at Sandy Island, we anchored just outside a coral reef and took the dinghy over to a beach we shared with almost no one, soaking up sun and dining on grilled lobster. 

We began our second Anguilla day with a short sail to check out perfect Anguilla beaches like Meads Bay (“We’re sailing ‘out here’” I yelled to my crew at one point), before coming back and dropping the hook closer to one of my favorite Caribbean beach bars, a watering hole called Elvis, and going ashore for a lazy afternoon. Over lunch at Elvis I briefed my crew on the appeals of Anguilla.

This island is known as a getaway for the rich and famous for plenty of reasons. One reason is Shoal Bay to the east, a beach rated among the Caribbean’s most beautiful (and it’s not even my favorite Anguillian beach). Another reason is Dune Preserve, boasting great views of St. Martin’s voluptuous skyline from Rendezvous Bay, an establishment CNN Travel once rated world’s best beach bar.

I suggested they grab a taxi in the parking lot right beside the dinghy dock and go exploring, though I was going to stay put. This was the perfect setting with fishing boats bobbing in the gentle surf, rugged cliffs towering above to our west, cliffs surmounted by villas sporting colorful roofs, decorated by great stands of cactus.

My crew opted to stay put, though some strolled down the beach, discovering an attractive boutique and Bernbaum Art Gallery. I did join them after sunset as we dined at an elegant restaurant called Sandbar, just one of several great dinner spots a short stroll from the dinghy dock.

Given Anguilla’s allure I found it tough to weigh anchor next morning but conditions were right for a passage and I wanted to finish up at Orient Bay back on St. Martin.

“Get strong east winds and big surf and you shouldn’t try to get into Orient,” The Moorings’ staffer Alcid Belgrave had warned me back at the chart briefing. The marine forecast seemed to be cooperating, so we got an early start and rode west on a broad reach before coming around to beat up Anguilla Channel, retracing our earlier course, though once clear of St. Martin’s eastern headland we bore off to a beam reach before painlessly achieving Orient.

Orient is famous in the Caribbean (or maybe that should be infamous, since it hosts a well-known nude beach) and it is spectacular. Two spots are acceptable anchorages, Ile Pinel and in the lee of Green Cay. Belgrave had counseled against anchoring at Pinel but it was known for good snorkeling and was home to a hopping beach bar so I wanted to at least check it out. After struggling to set the anchor, I finally motored over to Green Cay.

We were all happy with the choice. We dropped the hook in 8 feet of water and made the quick trip by dinghy to an arcing beach roughly two nautical miles long, a go-to spot boasting a wealth of beach bars
and restaurants.