The Merry Wives of the Windwards

A feature story from our November 2006 issue.


There’s nothing like a good paddle to get the wives Paula, Sue, and Peggy smiling again after a long morning of coffee, snacks, and girl talk aboard the boat. Mark Pillsbury

Hey, it wasn’t my idea to hustle rum into the Caribbean. It was the captain’s. And since the captain was the only man in our crew, packing strong medicine ranked right up there with swim trunks and toothbrush.

“There’s all the rum in the world in the islands,” I’d moaned while he madly obeyed the bareboaters’ packing rule. It was just past 5 a.m., our ride to Boston’s Logan Airport was about to arrive, and the captain unpacked, then repacked his clothes into a smaller, carry-on, soft-sided bag for our weeklong Moorings charter aboard a new Beneteau 44.3 out of Canouan, an island in St. Vincent and the Grenadines.

“Why are you bringing rum?” I stubbornly nagged.


“Long airplane ride.”

He had a point: It would be nearly nightfall before we were finally aboard and breathing a collective sigh of travelers’ relief. And I must admit, I was the first to hold out my cup for a drop while waiting for a connecting flight in San Juan, Puerto Rico. Then, less than 24 hours into the charter, anchored off a tropical island of nodding palms and fluffy white beaches, the captain was fresh out. He needed more, fast. But were the women aboard to blame?

If so, “the wives,” as he started calling us, were in no mood to accept blame; we were having way too much fun. And we were getting a kick out of the moniker, which was a play on our entwined relationships. The captain, also known as Mark Pillsbury, is CW’s senior editor and, thus, my co-worker. Crewmate Sue was his only real wife (at least as far as I felt comfortable probing!). The others in the harem were Peggy Fitzgerald, Mark’s sister-in-law, and Paula Devereaux, a friend of Mark and Sue’s from their hometown of Nahant, Massachusetts.


Paula, a successful lawyer, quickly grew tired of being called a wife, proclaimed she was useless in the galley, and went for the complex, alluring, and, yes, moodier title of “mistress.” She also paid for the kayak rental, so we put up with the whims of the Other Woman.

Then there was me. Besides brief reprisals of my former role as crewed-charter cook and mate (the “heads and beds” girl, in charterese), I was along for the ride as boat scribe. Though this was a foray back into the familiar Caribbean waters I’d sailed as a paid hand more than a decade ago, I had yet to explore many of the Grenadines south of St. Vincent. The adventure of actually chartering a bareboat with friends who are equally skilled sailors was as much a first for me as it was for them. Hands-on lessons in boathandling, sailing itinerary, and navigation awaited, and I was eager to brush up on skills that had acquired rust during eight productive years at a desk. I wanted to stand at the bow, eyeball a good anchoring spot, then let out the right amount of chain and attach the snubber. I wanted to know what it felt like to handle a Beneteau of a smaller size than the 50-footers I’d sailed aboard during previous charters.

So it all felt familiar, yet different. To boot, we’d see the islands in the off-season, which meant that the hundreds of boats normally cruising these waters from Christmastime through spring wouldn’t be there, and neither would the swells from winter northers, an inescapable fact of wintertime cruising.


Primed for fun in the sun, we pulled out our wish lists. Sue and Peggy seemed happy enough that the trip had come together willy-nilly to enjoy whatever we encountered. The Mistress fancied a landfall on Mustique, island of the rich and famous. I’d made it to Mustique in the past, but not farther south. Hearsay of winter resident Mick Jagger giving an impromptu performance at Basil’s Beach Bar, one of the island’s two bars, sounded too familiar to me. What danced away in my head were fanciful visions of Jack Sparrow, Disney’s favorite pirate of late.
Let’s head to the Tobago Cays,” I said to Mark. Maybe the Pirates of the Caribbean film crew had left behind a stash of bottles from the scene they’d filmed on Petit Tabac, one of its islets. Maybe they’d never left. Maybe Johnny Depp, or a bead or shell from his girl-boy pirate getup was still there . . .

“Hey, is that Baline Rocks?” asked Paula the navigator. I was daydreaming, but the Mistress was sharp and on the job.

Mark crouched down from behind one of the Beneteau’s twin wheels to scope out the electronic chart plotter. Mounted conveniently at the aft end of the cockpit table, we could see the readout from either helm, though we did have to hunch down to read the chart and the boat’s position.


We also kept the paper chart nearby to compare notes and orient ourselves. These tools, plus the excellent color skyline profiles of the islands’ landscapes in Chris Doyle’s Sailors Guide to the Windward Islands, helped us newcomers navigate fresh territory.

“No, that’s Catholic Island,” he replied.

While they sorted it out, Sue, Peggy, and I studied charts, read, and took in our surroundings of cerulean sky and emerald waters. It was all a bit numbing: The compression of activity in the previous two days, the hustle of getting from Boston to the southern Caribbean, then total immersion in boat operations, and a thorough chart briefing with Scott Cundy, The Moorings base technical manager, left our little crew a bit jet lagged, sleep deprived, and occasionally overwhelmed by the summertime heat, though the cooling trade winds never disappointed, whether we were under sail or at anchor.

There was also another reason for sleepless jitters: a heartfelt and stern warning came from The Moorings that a trio of armed break-ins and thefts aboard charter boats in the spring of 2006 meant we needed to lock up and look around. “The Moorings wants you to be aware and keep you fully informed,” Scott told us at our chart briefing. According to a report by guide author Chris Doyle in the June issue of the Caribbean Compass, the sailors’ newspaper published from Bequia, the company threatened to broaden the travel advisory issued to its Grenadines charter clients to a general warning against piracy in the region, but it wasn’t necessary; by May, The Royal St. Vincent & the Grenadines Police Force had arrested one suspect and put out a public search for the other. By July, the country’s coast guard had also stepped up patrols in the southern islands.

Detailed security measures Scott suggested included avoiding anchorages where we were the sole overnight visitors; locking the dinghy to the boat nightly; locking the dinghy wherever we docked or anchored; and always informing each other if we ventured in opposite directions. Given my lazy years in the Virgins, the advice I found hardest to accept, then follow, was to lock up the companionway at night and lock ourselves below. I was glad I packed super silicone earplugs; some of my mates weren’t as easily consoled, and through the first couple nights of our trip, any crunch, pop, or groan, any slapping of a halyard against a mast or rigging, kept them from sleep, as did the wind shifts at anchor.

As the week wore on, we sought out and gained perspective on the security concern from sailors who frequented these waters and from locals. By trip’s end, our crew was satisfied that, yes, bad things can happen anywhere (and they did while I cruised the Caribbean for six years in the 1990s, I reminded myself), but a healthy dose of street smarts applied to the water never hurts. It certainly didn’t keep us from exploring these lush islands or from staying at the anchorages we’d wanted to see.

With all this in mind, we created and then loosely followed an itinerary that revolved around our energy, the weather, and our wishes, among them my romantic preoccupation with a dandy of a pirate whose very nature was spawned by an amusement-park ride. As far as I was concerned, if we plopped down at the Tobago Cays the whole week, I’d feel like I’d died and gone to heaven.

Reason prevailed, and upon leaving Canouan, we navigated as much by sight as by compass to Mayreau’s Salt Whistle Bay. Here we kayaked, got acquainted with the galley, and some of us held a dawn yoga workout on the vast, crescent-shaped beach.

Yippee!-Tobago Cays was next. Then we figured we’d sail north, a little better than 20 miles, to Bequia, explore the island by taxi, then lazily run back downwind the 20-plus miles to Mopion, returning to Union Island, the west side of Mayreau, and, yes, make one more stop at the Cays (hooray!) before returning to the base.
This route meant we’d see the biggest of the southern Grenadine islands (Bequia), the smallest (Mayreau), the prettiest and oddest (Mopion) and the most protected (Tobago Cays) in the area. Good sailing distances and easy gunkholing among islands that seemed even closer to each other than those in the Virgin Islands filled the bill.
Departing Mayreau and threading shallow waters, we motored by Baline Rocks, keeping their hull-munching edges well to port of Galasminda, which flew the French flag of its owner, John Pierre Rennaud. What had appeared before us as one low-lying island gradually gave way to two, and among shores heaped with fishermen’s discarded conch shells, we slid silently between Petit Rameau and Petit Bateau.

The Tobago Cays is a tucked-in kind of place, a hideaway that privateers and troublemakers relish, an emerald gem of Mother Nature’s lush Caribbean riches. Recent rains had washed the water an even more glowing shade of green. Traditionally rigged passenger schooners kept their sails pulled tight over centerline to steady their hulls in the ever-blowing trade wind. Much as I thought I’d jump in on anchoring duties, I was so dazed by the glistening surroundings that I just stared out over the horizon. Before I knew it, Mark had picked a spot behind Horseshoe Reef, safely spaced among a couple dozen or so of the assembled mixed fleet, and Sue and Paula had dropped the anchor with the help of Galasminda’s electric windlass. We were there.

But instead of Jack Sparrow, before us stood, afloat in a skiff, one of the Grenadines’ quintessential, real-life characters: a boat boy. Elroy greeted us cheerfully, politely doled out advice, and, for we tropical shoppers, spread out a kaleidoscopic array of sarongs across the thwarts of his sturdy little boat.

“Don’t stand on the coral,” he advised. “Just give me a call and I’ll be at your service 24/7.”‘

Relations between sailors and boat boys, who are as much a staple of the southern Caribbean as sun and spray, always make for lively discussion. While some view their assertive and frequent approaches to boats as a nuisance, the fact remains that boat boys are an integral part of capitalistic island society, and sooner or later, if you cruise the islands, you’re likely to find yourself in need of their goods or services. This includes buying ice and supplies, though we declined their offer.

So a golden rule to follow, furnished by base manager Scott and by other sailors we met, is this: Always be polite. Be clear-yes or no. Agree on your price before service is rendered.

On our own, finally, in the cays, we spent our day snorkeling and marveling over the greens, oranges, and purples of the very healthy reef, its coral, and its crazy-shaped and- colored fishes, which Sue dubbed the “happy fish with smiles.”

After dinner, we stared up into the night sky awash in stars, and the captain proclaimed he’d met a lifelong goal to see both the North Star and the Southern Cross, though I never got around to verifying the identity of the white orbs of our stargazing session with an astronomer. But the captain was happy in the belief that he’d struck something from his life list, and we were now officially out of rum, so I wasn’t going to push it.

Bequia was our next destination, and we set out on this rollicking jaunt north early in the morning. This was the most adventurous gallop of our charter, reaching in 25-plus knots of winds that occasionally gusted to 30 or more, demanding that we pay attention to well-published advice to steer east, or windward, of the rhumb line to a northbound Grenadines destination, because the current runs west-northwest at about one and a half knots. We also followed the rule to secure the 9.6 horsepower outboard to a bracket on the pushpit, a daily workout that made the women crew grateful that our captain is a strapping fellow.

As grateful as I was for that, I cringed at his critique of my helming. He compared my time at the wheel of Galasminda to “an attempt to inscribe my name in the Caribbean Sea.” Oh, well. Oversteering has always been a flaw until I get acquainted with a boat, and this modern-underbody Beneteau was a long way from the heavy-displacement, full-keeled boats that I was used to. I still enjoyed the challenge at the wheel, but I was soon ready to give it back to Mark.

Flying fish dive-bombing into crests of waves entertained us; seasick crewmember Peggy worried us; but by the time we caught a mooring in Admiralty Bay, Bequia, and after the captain insisted-brutally, I thought-on a few more tacks into the harbor, Peggy was as good as new and game for exploration on land.

Bequia, at only seven square miles, is the largest of the Grenadines; compared to the Cays, it’s a bustling metropolis. Port Elizabeth’s downtown has banks, restaurants, an excellent bookstore, an open-air market, sail lofts, chandleries, and, yes, beverages. No need to plan a voyage seven miles farther north to St. Vincent, which locals call “the mainland.”

We liked Bequia (and its beverages) so much that we stayed two days. We visited the public library and chatted with Ann the librarian (the library welcomes donations of books; send them to Bequia Library, Port Elizabeth, Bequia, St. Vincent & the Grenadines). We strolled the quaint beachfront and gave ourselves a break from galley duty with dinner at the Gingerbread House. We took an island-taxi tour, and I got to visit all the spots I’d never had time to see while I was on charter a decade ago.

Among them are the Bequia Maritime Museum, where model boats are constructed; the Bequia Whaling and Maritime Museum, where Harold Corea showed us the harpoons his uncle, Athneal Ollivierre, used to spear humpback whales; and the Oldhegg Turtle Sanctuary at Park Beach, where fisherman Orton G. “Brother” King singlehandedly feeds and rehabilitates baby hawksbill and green turtles until they’re strong enough to survive on their own.

In 11 years, King says he’s released 800 turtles back to the sea. “It’s not just giving them food,” he told us. “It’s a lot more than that. You have to love it and have a deep interest in it and want to learn. Somebody got to do it. No better person than me.”

From each of these places we saw proof of the community persevering, against increasing odds, to hold on to aspects of its maritime heritage. Whaling, boatbuilding, and fishing still exist today on Bequia, though these activities are a shadow of what they were a century ago, and it now favors the more recent and increasing shift toward tourism, boat chartering, and related services.

And ever the publishing junkies, Mark and I also squeezed in a visit to the tiny offices of the Caribbean Compass, now in its 11th year. Our visit with the staff of Sally Erdle, her husband, Tom Hopman, and production editor and designer Wilfred Dederer left me reassured that in this cyber era there still exist paper publishers with a mission. “The idea from the very beginning was to be an ‘open source’ of information to cruisers,” Sally said. “The original concept was a little newsletter every other month of eight to 16 pages. The second issue was 32 pages. Now, if the Compass is one week late, the phone starts ringing off the hook. Cruisers still like to have something they can hold in their hands.”

After so much contact with civilization, it was time to return to some serious off-season quiet. Our remaining charter time was on the wane, so we lazily reached south in conditions that were kinder to our motion-sensitive crewmates. We put in briefly at Canouan to top off the water tanks, then scoped out and took a pass on Petit Martinique and Petit St. Vincent as blustery weather rolled in. (For the record, Grenada, Carriacou, and Petit Martinique, situated south of St. Vincent and the Grenadines, are a separate country; sailboats must clear in and out between the two countries, although many choose to chance it and visit Petit Martinique without attending to formalities.) We then managed a brief snorkeling outing, amid the showers of a light tropical wave, at Mopion, a dab of sand about the size of a helicopter landing circle but with a thatched umbrella all its own. This spot rivals the Cays in the health and color of its reef and fish life, but I advise serious caution when it comes to finding the coral-free path to shore. In other words, anchor the boat close by, then take the kayak or row the dinghy with the outboard up.

We overnighted at Union Island’s Clifton Harbour and were nearly the only breakfast patrons at Lambi’s, a huge waterfront restaurant, market, and inn. The food was plentiful and excellent, and some of it, like the homemade bread and jam, and a fruit plate and coffee, were served family style.

We walked off breakfast with a stroll through town, then climbed as high as we could up the stairs of Castello’s, a cornucopia of boutique, marine chandlery, art gallery, and brasserie on several levels. The reward was an excellent perspective of Clifton Harbour, and calories expended.

Back aboard, we motored around to the west side of Union for a lunch stop at Chatham Bay, probably the greenest, lushest, and quietest place I’ve ever experienced in the Caribbean. From the boat, we could see cattle lazily strolling the beach.

We chose to spend the last night of our charter at Saline Bay, on Mayreau. So we sailed the short distance from Union, anchored off the beach, and climbed the hill to call at Dennis’ Hideaway. A place known for good food and drink, set at the top of the island’s tiny fishing village, it was started 18 years ago by Dennis Forde, a Mayreau-born charter skipper. While we watched the sun set and took in the view, we were treated to a visit from the man himself. He urged us to pass along details that he’s putting the finishing touches on a swimming pool onsite, has air-conditioned rooms to rent at his inn next door, and will expand cruisers and charterers amenities to include a market, an internet cafe and water at the dock for visiting boats. Reach Dennis through his e-mail address (denhide@

OK. We’d had plenty of adventure, sailing, anchoring practice, and dinghy workouts. We chose, for the last few hours before returning to the base, to make absolutely certain that we missed no opportunity to find a pirate or his rum in the Tobago Cays. So to my favorite anchorage we returned. This time I helped drop the hook. We snorkeled. We dinghied over to Jamesby and were transfixed by the birds, crabs, and iguanas of this nearly untouched spot, and Peggy did her part for the environment by removing rubber flip-flops that had washed ashore. Still, conditions weren’t right to head out to the other side of the reef, to Petit Tabac. No Johnny Depp for me. But once again, a boat boy came to the rescue.

“Are you ladies enjoying your time in the Grenadines?”

“Oh, yes,” we assured Walter Bob.

“I hope you win the lottery and come back and give me some of the money,” he said to us, steadying himself aboard his skiff, Free Spirit II. “Now, make sure you get home in one piece so that you all can come back.”
No problem, Walter Bob. No problem at all. And next time, instead of relying on some Hollywood phantom, we’ll let you get the rum.

Charter Choices from St. Vincent to Grenada

Bareboat charter savings in the off-season range from 20 to 50 percent off high-season rates, according to several companies with bases in the region. In Blue Lagoon, at St. Vincent, charter options include Barefoot Yacht Charters (784-456-9526, Footloose Sailing Charters (800-814-7245,, Sunsail (800-327-2276,, and TMM (800-633-0155, In Canouan, choices include The Moorings (800-535-7289, In Grenada, charter boats are available from Horizon Yacht Charters (877-494-8787,

The Boat Boys Organize

Given the growth of tourism in the region, and the rise of security concerns, some boat boys have formalized the livelihood that puts food on the table at home. Their group, The Southern Grenadines Water Taxi Association, is registered with the St. Vincent government.

“Our duty is to protect and to preserve our coastal resources, and to bring all water taxis under our umbrella so that we can provide better service to our visitors,” board member and boat boy Sydney Dallas told me in an e-mail after our charter. Every taxi will be numbered and every operator will hold a license, he added. For more details, contact Sydney (socon

Elaine Lembo is CW’s managing editor.