A Windy Leeward Islands Charter

It was definitely blowy, but on a bareboat charter from St. Maarten to Anguilla to St. Barts, the gusty, switched-on trades were just part of the adventure.

August 11, 2015

Nearly every New Englander who sets forth for sunny climes in the dead of winter has an obligatory Terrible Travel Tale (TTT), and here’s mine. It was 4 in the morning on Sunday, March 8 at Boston’s Logan Airport in the terminal for the airline known derisively — and deservedly — as “U.S. Scareways.” Spring break had started the day before, so roughly 4 zillion college kids in something resembling riot mode were trying to escape what was literally the worst local winter in recorded history. As daylight saving time had commenced two hours earlier, springing the clocks forward, nearly everybody was functioning on the dangerous combo platter of a long night in the bars, zero sleep and max caffeine. And infinitely wise U.S. Scareways, naturally, had maybe four people on duty, one of whom was wandering through the multitudes trying to induce order from chaos.

Sadly, he was laboring under a serious wardrobe malfunction, which I tried to point out as gingerly, if directly, as ­possible. “Mate,” I said, “your fly is down.” With a quick, silent nod and a stealthy, quicker zip, he was gone. But the karma gods, thankfully, had noticed.

For when 30 minutes of going nowhere fast morphed into more than an hour, and it started to become terrifyingly clear that the odds on making my gate were getting long, suddenly my sartorially challenged acquaintance appeared behind a ticket counter and gave me a subtle high sign.


I weaseled my way around a pack of catatonic dudes mesmerized by smartphones, with the collective aroma of a half-empty bottle of stale Bud Light, all wearing Hawaiian shirts, cargo shorts and flip-flops (it was 12 degrees outside). Before I knew it, magically, I was boarding my flight to St. Maarten with, oh, eight minutes to spare. It appeared I would catch up with my girlfriend, Annie Lannigan, and her family for a bareboat cruise in the Leeward Islands after all.

So my TTT actually had a QHE (quite happy ending). And there’s a lesson there, fellow sailors and travelers. When flying, if you see a man flying low, go ahead and state the obvious. You just may be rewarded.

Several hours later, my jet banked hard for the famous runway into St. Maarten’s Princess Juliana ­International Airport — revelers on Sunset Beach can practically reach up and touch the plane’s landing gear — and the view of the yachts finishing the last race of the island’s annual Heineken Regatta was exquisite. After the slush and snow of Beantown, and the dank, dark winter, the sight of countless white sails casting shadows over wavy turquoise water was a visual treat.


Annie had arrived on a different flight a half-hour earlier, and together we grabbed a cab for the quick ride from the Dutch side of the isle to the Dream Yacht Charter base on the French side in Marigot. This was once a long, boring drive through bumper-to-bumper traffic in Philipsburg, but now takes minutes flat thanks to a new bridge that spans the Simpson Bay Lagoon. After checking in and stashing our gear, we found a nice seaside cafe, ordered drinks and waited for the rest of our crew to arrive: Annie’s brother Bobby and his wife, Christine; daughter Meagan and her fiancé, Jay; and niece Julia and her boyfriend, Chris. Once everyone was assembled, we walked downtown from Marina Port La Royale and had dinner at a delightful open-air seafood place. Marigot was blissfully, strangely quiet, as almost everyone in St. Maarten had ventured to Philipsburg for the regatta’s final, massive prize-giving blowout and concert.

We were in the islands. It was warm and mellow. Winter was someone else’s problem. Yay.

We also had places to go and things to see. The next morning we fanned out and got to it. Bobby gathered most of the gang and headed for the convenient supermarket within walking distance of Dream’s base, and seeing we were now more or less in France Lite, they returned with a veritable bounty of fresh baguettes and lots of cheap, delicious French wine and cheeses, among other delicacies. We had several good cooks aboard, and clearly they’d have plenty to work with.


Meanwhile, Annie and I got familiar with our ride for the week, a Jeanneau Sun Odyssey 509 called Fermi, which we could only surmise was named after Enrico Fermi, the late Italian physicist. Fermi’s famous “paradox” is the seeming contradiction between “the high probability that extraterrestrial civilizations exist and the lack of contact with such civilizations.” Coincidentally, I too have a personal, contradictory paradox: I sail over waters where many fish definitely exist, but lack the ability to catch them. Yes, the universe abounds with mystery. Yet I digress.

Besides, in the moment, we had other, more pressing earthly concerns: The easterly trade winds were honking, blowing the proverbial dogs off their chains. And bigger breeze was forecast. As we sat down for our chart briefing, the base manager, an affable Frenchman named Christian, glanced out his office window at the flapping awnings and slapping halyards, and said, “It is windy, no?” And it was supposed to get windier, he added, with sustained gusts well over 30 knots forecast for the middle of the week.

But Christian was a smart sailor, and when he heard our proposed itinerary, which included the islands of ­Anguilla, St. Barts and tiny, uninhabited Île Fourche, he proposed a ­clockwise ­circuit of all three that would give us a favorable slant on the trades with power reaches to each destination, including the final leg back to St. Maarten. Then, basically, he told us to get lost. “The last bridge opening into Marigot Bay is at 2:30,” he said, glancing at his watch. “You don’t want to miss it.”


Precisely on time, in the company of a small armada ­exiting the lagoon, Fermi coasted through the swing bridge to Marigot Bay and into clear, open water. The abrupt change of scenery, from the busy concrete quay to the bright, breezy ­Caribbean, felt like the moment in The Wizard of Oz when the movie screen switches from black-and-white to Technicolor. Christian had suggested we make a dash for customs, clear out of St. Maarten and rocket right over to low-lying Anguilla, but instead we dropped the hook, had a refreshing swim, mixed some cocktails and decided to stay precisely where we were for the evening. Ah. Sip. Exhale. Smile. Repeat.

As predicted, we awoke the next morning to a small gale, with a solid 25 to 30 knots of blast-furnace breeze. Luckily, it was coming from the east and we were headed west, so once the officialdom was addressed, we got underway.

It was the sort of day no mainsail was required, so we unfurled the jib and had a cracking great sail across the Anguilla Channel, which was flecked with whitecaps and, as we ripped onward, a roiling seaway with 4- to 6-foot swells. Yeehaw! Fermi handled it with aplomb, clipping along at a good 7.5 knots with occasional bursts into the 9s.

We scooted past ominous Blowing Rock and skirted the southwestern tip of Anguilla, then sheeted the jib home and slid along the isle’s northern shores, finally dropping the hook in Road Bay off the appropriately named Sandy Ground Village.

While everyone else hopped aboard the dinghy and headed in, Annie and I tidied up the boat and then split in opposite directions: She napped, I swam.

I washed up ashore in front of a beachfront watering hole helpfully called Le Bar, where the Fermi crew was assembled. Before I’d drip-dried, Julia handed me an icy bottle of Carib lager with a fresh lime popping out of its neck.

Life was exceedingly good.

A fabulous “home-cooked” dinner aboard followed, after which everyone dropped like flies. It felt like 3 a.m., but in fact was 9:30. It had definitely been a big one.

The next day was the squalliest of the week, which provided the convenient excuse to stay put. Anguilla is renowned for endless, world-class beaches, and a little wind and rain wasn’t going to deter the younger half of our team from inspecting them. So while they hailed a taxi and moved out, the rest of us hiked up the hill overlooking the bay to check out the view and grab some chow.

We ended up at a restaurant called E’s Oven, recommended by some locals, and enjoyed a spectacular lunch: lobster and bacon paninis, curried chicken wraps and lightly grilled fresh fish, all perfectly prepared. On the way back to the boat, we cleared customs so we could get an early start the next morning for our next, highly anticipated port of call: St. Barts.

At our chart session, Christian had recommended we round the northeastern end of Anguilla, through the Scrub Island Channel, before bearing away for St. Barts, which proved to be excellent advice. With a triple-reefed main and full jib, once clear of the island we settled into an absolutely perfect beam reach. Man, you can’t beat sailing, right?

Midway through the 20-odd-mile passage, after four days of howling winds that had built up seriously impressive seas of 8 to 10 feet (thankfully from abeam), it occurred to me, suddenly, that this was easily the wildest sail I’d ever experienced in more than a dozen bareboat charters. Sure, it gets windy in the BVI and other places, but not with the attendant open-ocean conditions. I reckon if you chartered in St. Maarten during a similar heavy-air week, and you didn’t feel up for the Big Sail, you could hang around the island, visit a different anchorage every night and have a swell time. But if you skipped the run south, you’d also miss the grand opportunity to have one helluva ride.

You’d also forgo the French West Indie isle of St. Barthélemy, aka St. Barts, perhaps the Caribbean’s greatest nautical theme park. St. Barts was just like Anguilla, but exactly the opposite. Sure, on the one hand, it was a Caribe isle surrounded by water. But Anguilla is funky, in the best sense of the word. St. Barts is a lot of things, but funky is not one of  them.

Once we’d arrived and dropped the hook off the bustling town of Gustavia, in the very first hour or so ashore, we witnessed:

1) A daredevil on a motorbike popping a wheelie the length of a long, crowded street, scattering the masses.

2) A fight between two idiotic crews in adjacent catamarans parked stern-to on the waterfront, the culmination of which was an inebriated sailor falling hard off the transom of his boat.

3) A group of weathered musicians in a small, open seaside home playing what I can only describe as sensational French zydeco. And …

4) The drinks menu of a sidewalk cafe with linen tablecloths, where cocktails cost 25 euros apiece unless you opted for a “bowl,” a 150-euro special serving six to eight. I stuck with a Carib, thanks, then bolted for Le Select, the bar Jimmy Buffett made famous, just to say I had.

If going from Marigot’s inner harbor to its lovely bay, as we had at the outset of our trip, was like visiting your neighborhood multiplex, traveling from Anguilla to St. Barts was akin to walking into the biggest, clearest Imax screen ever constructed. We rented vehicles — the kids opted for four-wheel-drive ATVs, the rest of us settled for your standard automobile — and rambled all over. The peaks, crannies and long vistas; the impeccable roads and precise stonework; the glorious, empty beaches and pure, inviting waters; the exquisite homes and wonderful restaurants were all utterly magnificent. So, yeah, St. Barts. Somehow, I’d never been there. But now I totally get it.

Of course, a lot of flash goes a long way, and after a couple of days in St. Barts, before we wrapped things up, we all needed a bit of time and space to decompress. We found the perfect place to do just that.

Before our charter, I’d swapped emails with my old friend Danny Greene, one of the original CW editors and a longtime Caribbean cruiser. He recalled that one of his favorite islands in the whole chain was little Île Fourche, a privately owned nature preserve where the only residents are goats, just north of St. Barts. Danny said to be sure not to miss it. Of course we had to have a look.

We sailed into the wide but protected anchorage and picked up one of the empty free moorings. The silky water was crystal clear, perfect for a snorkel among the fissures and caves along the steep shore.

At the head of the cove, we landed the dinghy on the sandy beach and several of us scrambled up the adjacent 400-foot pinnacle, which afforded broad views through the hazy sky of every place we’d visited. Sure, I’d bought a T-shirt or two, but the photos we snapped overlooking Île Fourche are my favorite souvenirs of the entire escapade. Too soon, we were hoisting sails once again, but the 25-mile sail back to Marigot, a lovely broad reach ultimately coursing past St. Maarten’s beautiful southern shoreline, was a terrific way to close out the proceedings.

The next day, back in the airport waiting for my northbound plane, I actually recognized some of the same ­familiar faces from the nightmare scene in the wee hours in Boston the week before. Gone were the baggy eyes, the pasty complexions and the general sense that the world was about to end. Everyone looked tanned, relaxed and very happy. Then again, even though everything had happened way too fast, so was I.

Herb McCormick is CW’s executive editor.

2012 Golden Rock Regatta

With St. Maarten in the distance, another bareboat slides past ominous Blowing Rock in the Anguilla Channel, off the southwestern tip of the island of the same name. Little did we know, our charter would take place during one of the winter’s windier weeks. © Bob Grieser/OUTSIDEIMAGES.COM
Once anchored in Road Bay on the north shore of Anguilla, there was lots to do and see, including this pretty little cruising boat short-tacking through the anchorage. unknown

spring commissioning

There are plenty of world-class beaches in Anguilla, and even the one fronting Road Bay is pretty good. © Bob Grieser/
On the breezy sail to St. Barts, Rhode Island waterman Jay Teeden proved to be a skillful helmsman. unknown
There were plenty of great cooks aboard the good ship Fermi, including Bobby Boyaval (left) and his wife, Christine (right). unknown
Skipper Annie Lannigan, pictured with daughter Meagan, assembled the crew for our charter adventure. unknown
Julia Boyaval, with boyfriend Chris Halliday, rounded out the team. unknown
Once in St. Barts, we dropped the hook off the town of Gustavia in company with dozens of other like-minded sailors. ©Bob Grieser/OUTSIDEIMAGES.COM
The bustling island of St. Barts just may be the Caribbean’s greatest nautical theme park, chock-full of beautiful boats, homes and people. It certainly attracts more than its fair share of superyachts, lit up stern-to along Gustavia’s quay. ©Bob Grieser/OUTSIDEIMAGES.COM
For those with more modest bank accounts, you can always grab a beer at Le Select, where Jimmy Buffett once plied his trade. ©Bob Grieser/OUTSIDEIMAGES.COM
Our Jeanneau Sun Odyssey 509, Fermi, handled the shrieking winds and big seas with aplomb. After the hubbub of St. Barts, we sailed north to tiny Île Fourche to decompress. unknown
The view from the island’s small peak was worth the scramble to its summit.

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