The Incomparable Lesser Antilles

It’s as though God and Walt Disney got together and said, ‘Let’s make a cruising paradise for yachtsmen.’
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If you’re passing from St. Maarten to St. Barts, take a break at Île Fourchue for a swim. An empty mooring may be waiting. Cap’n Fattty Goodlander

Fifty-six years of offshore cruising, spread out over more than 100,000 nautical miles, has convinced me that the Lesser Antilles are, in my humble opinion, the best place to charter on this planet.

Frankly, nowhere else even comes close.

Sure, Tahiti is nice, we love Tonga, and it’s great to see the charter fleets expanding in Thailand, Mexico and Greece. But none of these destinations holds a candle to the Eastern Caribbean.


Why? Diversity and conditions.

The winds, seas and harbors in the Lesser Antilles are nearly ideal 99 percent of the time, and landfalls are perfectly spaced. In many of the most popular chartering waters, destinations are 30 to 40 miles apart — or less. This means you can get up at a reasonable hour, have a thrilling sail, and still manage to clear customs (if need be) by happy hour. And sprinkled among these rousing passages are locations where you can harbor-hop and laze about to your heart’s content. It’s as though God and Walt Disney got together and said, “Let’s make a cruising paradise for yachtsmen.” Sailingwise, stretching from the Virgins all the way south to Trinidad and Tobago, the Lesser Antilles win easily. Nowhere are the breezes better, the sands whiter, or the harbors wider and with better holding. Even if you never step foot ashore, charter in the Eastern Caribbean at least once in your lifetime.

But really, you should stop and step ashore — as often as you can — because it’s the dynamic cultural diversity that really sets these lovely isles apart. Laid-back Culebra, in the Spanish Virgins, dances to a salsa beat that’s totally different from bustling St. Thomas, in the nearby U.S. Virgins, with its nine-cruise-ships-a-day commercial tempo. The British Virgin Islands’ Tortola has a proper English accent, true, but isn’t quite as Anglicized as Anguilla, which actually welcomed its English invaders ashore with Earl Grey tea and crumpets.


In Culebra, my wife, Carolyn’s, and my favorite anchorages are in Ensenada Honda, due east of Dewey, or in Ensenada Dakity Bay, just west of the reef entrance. Our top spots in the U.S. Virgins are Long Bay, on St. Thomas; Flamingo Bay, on Water Island; St. John’s Round Bay; and the north side of Lovango Cay, between it and Congo Cay.

We like every anchorage on Jost Van Dyke, in the British Virgin Islands, and ditto for the waters around Great Camanoe, north of Tortola. Eustatia Sound, at Virgin Gorda, has lured us back repeatedly as well.

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When you visit Antigua, climb or take a taxi to Shirley Heights, where the view of English Harbour and Falmouth Harbour beyond it are simply spectacular. Cap’n Fattty Goodlander

Heading down-island, in Anguilla we hang in the main anchorage of Road Bay, off Johnno’s, a local hangout, with Mead, Barnes and Cove bays as alternates.


Across the Anguilla Channel lies Sint Maarten/Saint Martin, an island so bipolar it can’t even agree on its French or Dutch name. Looking for pastries? Marigot is the spot. Marine supplies? That would be the Simpson Bay area, where all the stores, boatyards and marine services have complimentary dinghy docks (and free propane drop-off and pickup, too!).

We love to tuck behind the reef at Orient Bay — the only problem being disrobing if we want to go ashore. (This is the nudist haven of the Caribbean.) The good news: If Philipsburg on the south shore is rolly, Marigot on the west side is flat, and vice versa.

We call nearby Gustavia, on St. Barts, “Star Harbor” because one drunken night in the local watering hole, Le Select, with half of Hollywood half-naked on the dance floor (Treat Williams, Harrison Ford, Elliot Gould and Raquel Welch — not to drop names), I slurred to the sloshed woman next to me, “Wow, it looks like we’re the only two nonstars here!” to which she replied haughtily, “I’m Elizabeth Ashley, the actress.”



Yes, St. Barts is trendy, and I’ve slithered through its gutters with many a French sailor, stoned Rasta and even Timothy Leary’s trippy wife. And the harbor is certainly not devoid of musicians. I’ve seen Jimmy Buffett and Mishka and Heather Nova Frith playing on the deck of the doubled-ended gaffer Moon until the wee hours of the morn.

We usually use Île Fourchue as a lunch stop and anchor off Anse du Corossol (just out of the power-plant exhaust) for Gustavia. Baie St. Jean has a fine view of Île Coco (Cock Rock — you’ll know it when you see it). And yes, that’s a Swedish accent you hear mixed with the West Indian patois on Barts. The island of Saba has a treacherous anchorage that regularly eats unattended sailboats, but it’s perhaps the most charming isle in the Caribbean, and the only place elderly Dutch ladies shyly hustle you to buy their handmade lace. Anchor by Ladder Bay off the Steps and be prepared to roll your guts out.

Just to leeward of St. Barts is Statia, more formally known as St. Eustatius, where the police department used to have a weathered sign on its door that instructed you to fill out the nature of your emergency on the paper pad provided. It then instructed you to return home and be assured an officer would follow up in due course. The last time I was there, I partied with some local layabouts who were pissed off at a guy named Rodney (as in British admiral George Rodney), who did a drive-by on the island in 1781 and swiped it from the Dutch, only to lose it again a short time later. On the plus side, they’re still proud of being the first nation to salute the American flag, on the transom of the brig Andrew Doria in 1776. We anchor in Oranje Baai just off the town, north of the jetty.

St. Christopher, better known as St. Kitts, is still almost untouched by time. The big harbor is at Basseterre, but I prefer Shitten Bay and Ballast Bay to the south because Basseterre is often too loud and the anchorage too rolly.

Nevis, the sister isle to St. Kitts, is still celebrating its favorite son, Alexander Hamilton. When we last visited, we found it as laid-back and quaint as ever. Check out the estate where Horatio Nelson married his wife, Fanny. Anchor just to starboard of Charlestown and to port of the three-masted Herreshoff schooner Star. When you do, shout ahoy to Steve and Irene Macek for me. (And while ashore, don’t miss the natural steam bath; ditto the hermitage.)

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On Sundays, that’s where the party will be. Shops, restaurants and small ­resorts crowd the main street in Marigot, on the French side of St. Maarten, or St. Martin, as it’s called. Cap’n Fattty Goodlander

Next stop to the south, there was once upon a time a lovely little town called Plymouth on the Emerald Isle named Montserrat. Here was a bar called Agouti Brothers, where Elton John, Paul McCartney, Sting, Stevie Wonder or Mick Jagger might be nonchalantly sitting in with the local lads while chilling out from recording at nearby Air Studios, owned and operated by the fifth Beatle, George Martin. (Yes, Jimmy Buffett, with amazing precognition, recorded his Volcano album here long before the island blew its cork and smothered the entire capital of Plymouth under many meters of ash.) Nowadays, yachties frequent Little Bay, just south of Rendezvous Bluff, where they find a customs office at the base of the pier.

Redonda, just northwest of Montserrat, can be an OK lunch stop in settled weather, but don’t attempt to climb King Juan Peak. We once had a cruising race from Antigua that used Redonda as a mark, and required the (usually inebriated) skipper to climb to its summit as part of the competition. Alas, with a number of out-of-breath, overweight and intelligence-challenged skippers on the slippery slope, there was a slide. It might have killed the participants if they hadn’t had their bones so well lubed up with local rum.

Antigua can be utter magic; it’s an isle of amazing contrasts. The pizza joint between English Harbour and Falmouth Bay used to have a pool table beneath a blackboard where a guitar-picker named Eric would write his name to await his turn. (Clapton was establishing Crossroads, perhaps the trendiest rehab house in the world.)

But the oddest things happen on Antigua. My buddy Miles Stair, of St. John, was passing by a little beach rum shop when the elderly West Indian owner accosted him and asked him to help drag out an unconscious customer. Miles was in a hurry and did not appreciate being delayed. So he was none too gentle with the drunk, bouncing his lolling head over the doorsill in his haste. Hurried as he was, it seemed to him that the guy was wearing a vaguely familiar skull ring, so Miles rushed back, shook the stoner semiawake, and said, “Keith?” (The only thing he knew for sure was that Mr. Richards wasn’t in Antigua for Crossroads!)

Then there was the night at St. James Resort with Great Lakes racer Don Wildman and the crew of the Charlie Morgan-designed 12-Meter Heritage. I was the navi-guesser aboard, and that evening I swooned in the arms of Michelle Phillips of the Mamas and Papas — probably a story better left for another time. Ditto wiping the keel off that Baltic 49 with Timothy Stearns. (Oh, the shame!)

Actually, the more I remember about Antigua’s English Harbour, the more I realize how much I have sensibly repressed. Besides, these days, we usually anchor in Falmouth, although Five Islands, Dickerson’s Bay, Parham, Green Island and Nonsuch are all fun.

Guadeloupe, the Butterfly Island, feels like an exotic port of call. When we visit, I start off by anchoring in Deshaies and going ashore to find one of those well-proportioned mamas selling homemade coconut ice cream from a sweating wooden bucket. It’s out of this world in richness. Pointe-a-Pitre is worth a visit, but it is the nearby Les Saintes that remind me of the Society Islands in French Polynesia.

Dominica still has a voodoo vibe, with the waterfall in Portsmouth well worth the trip. (Yes, hire the local guide, and make sure you agree on price beforehand.) If we plan on visiting Roseau, we drop the hook off the Anchorage Hotel, just to the south.

French Martinique is one of my favorite stops. Check out the Volcano Museum in St. Pierre, where it is sometimes possible to get out of the roll by anchoring close in, just south of the dock. There were only two survivors of the 1902 eruption of Mount Pelée, deemed the worst volcanic tragedy of the 20th century. One was a badly burned convict named Louis-Auguste Cyparis, who was found in a dungeon. When he discovered his jailers were all dead, he glibly claimed to be detained for a parking violation or something equally innocent. The only other survivor was a shoemaker named Leon Leandre. All of the remaining 29,933 residents died.

I always anchor off Fort-de-France to clear customs, then move to Pointe du Bout or Grande Anse. Don’t attempt to go ashore at HMS Diamond Rock. My buddy Jol Byerley tried it one crazy night, and ashore he drunkenly hoisted the Union Jack and created (literally) an international incident. The hangover was epic.

Farther south lie the Windward Islands, each as beautiful as the next.

Bequia and the Grenadines retain much of their charm. We used to send our daughter, Roma Orion, to school in Hamilton while anchored in Admiralty Bay, Bequia. She was the only non-West Indian in the school. I sent her class picture home to Carolyn’s Italian relatives in Chicago, along with a note that read, “Roma is the one in the yellow shoes.”

Sally Erdle, a fellow circumnavigator and marine journalist, still lives in Bequia, where she edits the Caribbean Compass. We’ve had a mutual admiration society going for over three decades now; Sally is a literal and literary delight. Cruising guide author Chris Doyle still occasionally short-tacks up the bay as well.

If you charter out of St. Lucia and sail south, or north from Grenada, an absolute must-stop is the Tobago Cays. The archipelago reminds Carolyn and me of both Beveridge and Minerva reefs, in the Pacific. But wherever you drop the hook, the truth is, the Lesser Antilles have an embarrassment of riches for the cruising sailor or charterer on holiday. It is easy to thoroughly blow through a week or two on a vacation sail — or even a decade or two, as we did while cruising on Carlotta, Wild Card and Ganesh.

Cap’n Fatty and Carolyn Goodlander, aboard Ganesh, are currently wrapping up a number of literary projects before heading northward to haul out in Langkawi, Thailand.