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car-anguilla-largeI didn't see much on my first cruise through Anguilla Passage in the Leeward chain of the Caribbean Sea. I was crewing for Steve Fossett on a one-hundred-twenty-five-foot catamaran called "Playstation" and we were chasing the Heineken Regatta's round-Sint-Maarten record.

This time it's different. We pull out of Oyster Pond on "Notos", a Gibbsea 43' we've chartered from Sunsail, we fly up the east coast of Sint Maarten pounded by a procession of angry beam waves and we turn west. The wind chases our stern on a broad reach and our boat romps like a filly on an April afternoon.

Off our port beam the mountains on the French side of the twin-nation island fade into the distance, fronted by the kaleidoscope roofs of Marigot, dominated by a seventeenth-century fort squatting atop one hill. The gently sloping silhouette of Anguilla luxuriates lasciviously off our starboard beam.

This time we are in no hurry, rounding the cactus-studded islet called Anguillita – little Anguilla – for Road Bay on Anguilla proper. Today is a day to be savoured. Today we are sailing for the stars.

It is no idle quest. While we encounter first some cumulus clouds, followed by a platoon of line squalls and a promissory rainbow, once ashore on the eel-shaped island (that's what Anguilla means in Spanish) we are star-struck.

"Uma Thurman is here," says the waitress at Barrel Stay just down from the dinghy dock at Road Bay. On a tiny island called Scilly Cay, a restaurant perches seaside. The proprietor, a gentleman known as 'Gorgeous,' gives us the tour. He points out a helipad where the haute-monde make their entrance.

"But if I reveal our guest list," he says with a grin, "I'd have to kill you." We have it on good information J-Lo has eaten here, Robin Williams, DeNiro. And, one day that week, we join this star-studded cast.

On our first day out, beating up the north coast, we share the waters with mega-yachts galore. The resorts on shore, some squatting atop pumpkin-coloured cliffs, some snugged down beside secret beaches, wouldn't be out of place in St. Tropez. Winds are great but the island's orientation, sort of a diagonal across the lat-long, keeps the waters flat.

"Anguilla isn't for everyone," says Sebastian, the Sunsail representative, at the morning chart briefing. "Cruising fees are expensive. But you have some great little passages and a whole bunch of amazing restaurants." He pauses. "And a couple of great anchorages."

In his Cruising Guide to the Leeward Islands, Chris Doyle calls Road Bay "one of the most pleasant anchorages in the northern Leewards." Early one morning I sip coffee in the cockpit and watch pelicans soar overhead, plummeting to the water with great splashes. Cliffs surmounted by mansions rise up over a brown sugar sand beach where a little bar called Johnno's, famous for its nightly live reggae, lazes like a liquored-up sun-worshipper.

Ashore I meet a distinguished gentleman pruning roses outside his period plantation house – and later discover that he was once chief minister of the island.

Sir Emile Gumbs squints seaward with a wistful expression. "Which boat are you on?" he asks, then pauses. "I'd rather be sailing."

His attitude – that love of the sea – is both widespread and appealing. It's an attitude that makes you want to spend time ashore. But be forewarned – you'll be in no hurry to weigh anchor.

We, however, find the ideal compromise. We leave the boat on the hook for a day, touring Anguilla itself, then we sail off to a regular Robinson Crusoe pair of islands called the Prickly Pears roughly fifteen nautical miles northwest. Then we come back and anchor at Crocus Bay, snorkeling and dinghying to a secret beach snugged down at the base of a fifty-metre cliff.

Today we move slowly – dining at the Pumphouse at Sandy Ground, sipping a blended rum at the Pyrat Rum Factory ($180 U.S. for a 750-ml bottle), grabbing a cab and doing the sunset at Barnes Bay.

Tomorrow we'll race down the coast on a broad reach, hardening the sheets and crossing Anguilla Passage for the casinos and nude beaches of Sint Maarten.

But yesterday we meshed with the rhythm of this place, setting out on a leisurely passage to Prickly Pears.

There we discovered a little bay fringed by striated rock and prickly pear cacti punctuated by the occasional palm tree.

We dropped anchor and negotiated a tricky little channel between the two islands in the dinghy, pulling up to an alabaster strip of sand. Four other boats – shallow draft power cruisers – were anchored here but we snorkeled the reef here undisturbed and stretched out on a beach we had completely to ourselves.

Back on "Notos", Claire Gorman had scullery duties. Her and husband Gerry, seasoned sailors, helped up run the boat – and did their part in depleting the rum rations.

The boat swung lazily at anchor, showing off the gently sloping indigo silhouette of Anguilla, the rounded hills of St. Martin floating above the horizon like a Caribbean mirage.

Claire poured the wine and brought out pre-lunch hors d'ouvres. Jerry hunkered down in the cockpit seat. He shook his head as if in disbelief and smiled. "Worse places to sail."

It was a while before I responded – staring out at the impossibly green waters, the purple hump-backed horizon.

"Five stars," I say desultorily. "I give it five stars."