The Caribbean Multihull Challenge Rally

What do you do on a boat for days on end if you’re not constantly tweaking the sails to get an inch ahead of the boat next to you? For cruisers and powerboaters, it probably seems like a dumb question, but when I arrived in Sint Maarten for the Caribbean Multihull Challenge Rally in February, I genuinely wasn’t sure. I’d never been cruising—unless you count a single night moored off an island after a race. Judging purely by the number of designated sunbathing spots on some cats, I assumed there’d be a lot of sitting around cultivating skin cancer and not much else.

That’s my secret: As a lifelong racer, cruising never appealed to me much.

Nevertheless, it was hard not to be excited when I arrived at Dream Yacht Charters’ base in Anse Marcel, Saint Martin. Our boat, a Lagoon 45, was parked at the dock in a stunning little basin surrounded by steep, verdant hills that jutted seemingly straight out of the water. It was too beautiful not to appreciate how lucky I was to be there.

The next morning, the boat’s skipper, Hans, met me for the boat briefing. We’d been paired up to sail together in the Caribbean Multihull Challenge (CMC) Rally for the next three days. Though the CMC has existed as a race for several years, this was to be its first edition with a rally fleet as well. Since charter boats aren’t usually insured to race, we were really benefiting from this addition.

So was the CMC. The event jumped from 14 boats the previous year to 29 boats this year, a big part of that being the 12-boat-strong rally fleet. Plus, the rally paired with Balance Catamarans to celebrate the company’s 10th birthday, bringing six Balance 442 and 482s to the fleet. The premise behind the rally, CMC’s volunteer Director of Marketing Steve Burzon told me, was that most cruisers sail with a full boat, which makes for slow going, especially on a multihull. A rally allows them to participate in the event without the pressure of racing.

But to ensure that it remained a rally and not a race, Steve was careful to establish some guidelines, like referring to the start and finish lines as “departure points” and “arrival points.” We all struggled to leave the standard terminology behind, and, “Guys, it’s not a race,” instantly became a running joke within the fleet.

The rally around the bi-country island of Sint Maarten/Saint Martin consisted of three legs, 10-20 miles each, taking us from Simpson Bay to Anse Marcel, then across the channel to Anguilla and back to Simpson Bay. At each stop, there were events planned for the evening and customs officials on hand to help with clearing in and out (technically each of the rally’s three nights landed us in a different country).

Hopping on a boat for a week with a stranger is always a toss-up, but to my relief and delight, Hans was a kind, measured sailor, with plenty of experience delivering cats. We were happily in accord about not needing to fill empty airtime with chatter.

To reach the start in Simpson Bay, we needed to leave Dream’s idyllic little basin, negotiating a meandering cut barely wider than the boat itself. The Dream Yacht staff was more than happy to hop aboard and do the tricky bits for us. I was unable to hold back an audible gasp upon realizing that the trees surrounding the canal were ripe with iguanas, each the size of a fat house cat. My local companions laughed as I scampered along the side deck, trying to get the perfect photo of a creature that’s probably as common as a squirrel to them.

The cut then poured out into a quintessential Caribbean inlet with sea turtles periodically surfacing and water a color that doesn’t exist back home.

We were heading upwind to make the pre-start events in Simpson Bay, so the plan was to motor, somewhat to my chagrin. I wanted to be sailing, not sitting around. Once we got a little ways from shore, though, the dramatic shapes of Saint Martin’s volcanic mountains plummeting into the ocean revealed themselves. It was impossible to be bored or unimpressed, and I watched the shore go by for hours. Occasionally, Hans would point out features of the coastline or clusters of houses belonging to notable people.

Simpson Bay is guarded by a single drawbridge that only opens a few times per day. We arrived well ahead of schedule, so Hans talked me through his preferred anchoring procedure, and we practiced on the soft, sandy bottom.

Still, we had over two hours to wait before the next bridge. Despite my earlier reservations, I managed to stay well occupied by swimming out to check our anchor, taking a thousand photos, and getting started on a biography I’d been meaning to read for years.

Day One

The next day, we were up and out for an 11 a.m. rally start that would have us retracing our steps to Anse Marcel. Despite a sustained breeze of 17 knots and me being a bit of a novice with electric winches, we hoisted the main without drama. The reaching start was meant to begin with the slowest boat in the fleet followed by another boat every minute until the fastest was off the line.

This was … ambitious, largely because most cruisers with their heavy boats and new crew members aren’t exactly set up for the precision of a 60-second start window. But it did make for an excellent opportunity to see each of our fellow ralliers up close and personal as they passed us by. Unlike in a race though, it was done with big smiles and waving hands instead of screams of “Leeward boat, HOLD YOUR COURSE!”

These close encounters added some excitement, as did watching a headsail on the Balance 442 Umoya go slack and then shred itself to ribbons, seemingly unprompted. Hans and I gawked and speculated.

To get to Anse Marcel, we had to beat up the Anguilla Channel. Charter cats aren’t known for their ability to tack close to the wind, and true to expectation, we were struggling to maintain our speed above 60 degrees to the wind. The upside of this was that Hans and I got plenty of tacking practice, and soon I was confidently managing the spaghetti, anticipating which adjustments would be needed next, and which lines to move to which winches ahead of time. We made it to the “arrival point” last, but consoled ourselves that it was only our first day sailing together and we were the only boat with just two sailors.

Onshore during the daily après-sail party, the other sailors asked how we did. When I said DFL, they playfully reminded me that it “wasn’t a race.”

Day Two

On the second day we were met with 20 knots of breeze funneling down the Anguilla Channel. One reef in, we cruised along pretty comfortably, with rolling waves buoying us along at 6-7 knots. Hans and I had spent the previous day primarily in companionable silence, but on day two, Steve’s wife, Nancy, joined us, generally improving quality of life on board with fresh conversation and colorful plates of sliced fruit.

The sail was beautiful, and once again, the slow-to-fast starting order had the rest of the fleet parading by us throughout the day.

One benefit of the “it’s not a race” mentality was that we were treated to views of some fun sail configurations, including Umoya’s ripped screecher replacement—an unusual symmetric spinnaker with a slice across the middle of it fitted with a lateral secondary kite. Without a main up, they were closer to our speed, and Nancy and I marveled over the sail for what felt like an hour. Later the skipper told me the strange kite was so low maintenance that while cruising, they once set it and didn’t touch it for a week.

As we rounded Anguilita and headed up the coast, I ducked below to grab my jacket.

“Are you cold?” Hans asked incredulously.

“No, just trying to avoid too much sun.”

“Good,” he nodded. “I’d have to make fun of you if you came all the way from the New England winter just to be cold in 80 degrees and sunshine.”

The joke was on him, though, when 20 minutes later I pointed out a grey blur obscuring the horizon. He ducked below to grab his jacket too.

Sure enough, a squall was bearing down upon us, and the breeze plummeted. We sludged along at 3.5 knots until the driving rain started, huge drops pinging off the boat. Then the wind spiked up to 30 knots. As the rig groaned and we surged along, I found myself thinking that 20 versus 30 knots of breeze didn’t feel all that different with the reef in. It was a solid boat.

We weren’t exactly sure where the “arrival point” was in the little inlet on Anguilla, so we took our sails down with some lead time. Hans and I had been debating how to get the jib in properly all afternoon since the furling line couldn’t run to the boat’s sole electric winch without bisecting the wheel. After manually cranking it in from the side deck via a winch above my eye level the day before, we were convinced there had to be a better way.

This time I tried sitting up on the coachroof for a better angle, but it was immediately clear that this was also the wrong choice, since I only had my knees to hold on with, and squall number two was picking up. Panting, I eventually got it done while Hans cheerfully reminded me that I’d asked for this.

Then it was on to another adventure in the form of climbing the mast steps to claw the main down. The cool rain started to pepper us again, and standing on one foot, head about 15 feet above the trampoline with only one hand to hold on with, I had vague regrets about not going to the gym more often.

While we were fussing with the sails, the Balance 442 Sage, who we’d been toe-to-toe with all afternoon, slipped by unnoticed. At a beach bar that night—while watching the Balance owners gleefully taking on Balance’s CEO Phil Berman in beach volleyball—Kayla from their crew flagged me down.

“I saw you up there grinding that sail in, and was like wow, that girl’s tough! She knows what she’s doing!”

I laughed and explained the confusion about how to run the jib furling line.

“We were all wondering why you’d stopped before the finish. You almost had us.”

“Well,” I joked, “it’s not like it’s a race.”

That night Hans and I were joined on board by Steve and Nancy. It was Steve’s birthday, so we capped off the evening in the cockpit with drinks and admiring the moon, which hung low over a constellation of mooring lights. Personally, despite my jelly arms and rash of mosquito bites, I was feeling pretty good about it all, swinging gently on the hook in our own private Milky Way.

Day Three

The rally concluded the next day with one last leg back to Simpson Bay, comprising a sleigh ride down the coast of Anguilla, hooking a left around Anguilita, and then coming up close hauled to follow Sint Maarten’s coast the rest of the way to the “arrival point.”

Raising the main in 25 knots proved difficult since it was flogging so hard that I needed to time pulses on the electric winch perfectly to thread the sail between the lazyjacks on the way up. One particularly bad snag had me squirreling back up the mast to pull the sail down and start again.

Once it was up, though, we were able to wing out the jib and skate along. The wind had eased to the low 20s, gusting high 20s, and Hans and I cheered on the SOG as it edged closer to 9 knots, eventually hitting the bullseye for a split second.

Bending around the islands and influenced by frequent squalls, the wind was weird all day, and when we hardened up, it made for a rough ride. It was back to just Hans and me on board, which was probably for the best because it’s hard to imagine anyone spending that day in the salon and not getting viciously seasick.

For our part, Hans and I stayed perched up at the helm as usual, save for the one time when a drawer in the galley burst open and sent plates clattering across the floor. I dashed down to tidy up, and fortunately nothing was broken. Still, it was a testament to how much slamming around we were doing, beam to the swell. And we couldn’t ease off because we were making ground on Sage, who we now considered our esteemed rival.

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We had to do one tack over to the finish, which Hans may have overestimated my ability to anticipate. I was mid-shifting the traveler as we came up, meaning none of the jib sheets had their cams set right or were on the right winches. This led to the (newly) windward sheet getting jammed in place. Eventually we got it right, but only after some…strategic floundering. Still, there was no yelling. Coming from Hans, I wasn’t surprised, but it was a welcome relief. Maybe my racing days had gotten me too used to skippers with bad habits.

After our moonlit drinks the previous day, I had lain awake thinking about the jib furling line again. Fortunately, I’d had an a-ha moment just before drifting off. As we approached the finish boat, I explained my plan to use the regular winch as a turning block and run the furling line to the electric winch around it. Hans considered it for a moment and gave me the go-ahead to rig it up. It worked like a charm, cleanly tucking our sail away as we reached the “arrival point”—once again DFL.

When all was said and done, the truth is I was wrong. Somewhere between hanging off the mast steps in a squall and hitting 9 knots surfing in the channel, I had to admit the rally had been an adventure, complete with all of the teamwork, and yes, even some of the competition that made me fall in love with racing. There was nothing boring or idle about it, and in the moments when things did slow down, I appreciated that too.

Consider me a rally convert.

For more on the CMC, visit caribbeanmultihullchallenge.com