Our writer recalls his favorite moments from 18 Figawi races across Nantucket Sound

Photo by Blake Jackson

“We are gonna hit that boat!” The man yelling those words over the wind, out in the middle of Nantucket Sound, was my first Figawi captain.

Boats at sea are not democracies. The captain’s rule is law. But we had a little parliamentary problem on board. This captain was brilliant. He was—quite literally—a rocket scientist. In fact, let’s call him Rocket Man. Genius? Yes. Decisive? Not so much.

The first mate and most of the crew were screaming at the helmsman to, “Round up, round up!” But the captain was yelling, “Fall off, fall off!” Either maneuver would have saved us. Rounding up would point the bow into the wind, slowing her. Falling off would further fill the sails with wind and speed us up.

But we did neither. We started to tack, but then didn’t. Now, flapping sails added thrashing, taut-snapping sounds to the noise of confusion on deck. I was caught mid-tack, in no man’s land halfway across the cabin top, when the captain started screaming about the imminent collision. I grabbed a deck rail and braced for impact.

Photo by Blake Jackson

There sits on the wall at Baxter’s Boathouse a modest little jug. Few notice it in the corner of the venerable Hyannis Harbor restaurant. The jug was the first Figawi trophy in 1972, now under the same roof where the famous race had its beginnings as a simple bar bet. The particulars are lost to the rum-scented mists of history and the accretion of legend, but the crux of the conversation reportedly went like this:

“I can sail to Nantucket faster than you.”
“Oh yeah? Care to make it interesting?”

Three boats sailed that Memorial Day weekend. Bob “Red” Luby raced first to the island, with brothers Bob and Joe Horan nipping at his heels. The next year they drew 15 boats. Now, hundreds of boats, thousands of racers and many thousands more spectators follow the festivities. The little jug at Baxter’s is immemorial, and now winners in the various classes are presented with gleaming silver platters and torso-sized trophies.

Most sailboat races, from the Olympics to the America’s Cup, are buoy races—sailors follow a fixed course around floats. But the Figawi joins the ranks of the Newport-Bermuda and the Sydney-Hobart as races that actually go someplace.

It’s a timelessly enchanting notion, to pack a bag and sail for unseen shores.

I chanced into the 1994 Figawi on a negligible invitation. A friend kindly lied about my sailing credentials, and suddenly I was crewman on a boat that would take a fourth-place trophy. My rampant under-qualifications were mostly hidden by my assigned job, that of “rail meat,” which is what they call the guys they stick up on the windward rail whose main job is counterbalancing the boat on upwind legs. You basically get soaked with cold sea water for five hours.

Between the thrills of racing and the social scene we found once we hit the docks, one Figawi was all it took. Excepting my own college commencement, I haven’t missed one since. I’ve crewed on five different craft. I’ve gone on boats that won silver platters, and I’ve been on boats that nearly sank. It’s never dull.

After that memorable first race, my buddy Slick—he now makes a living on boats and does not wish to be identified here—thought we could make our own run at glory on a Helms 24-footer that sat for years on stands in his backyard. It was full of water, which turned to ice and sagged the belly. It looked about as sleek as a jelly doughnut.

We mustered a crew. Slick would be captain. With one Figawi under my belt, I was de facto first mate. Two others had only been on motorboats, and my college roommate had never been on a boat of any kind—including ferries. The boat we spent the spring refurbishing was named Bulletproof. But it wasn’t even waterproof. It leaked. I’ve been in drier Jacuzzis.

Race day arrived with a misty morning. We sailed in circles toward the starting line, doubling back every time we fumbled another piece of equipment overboard. There went the winch handle, then the jib bag. Then some battens flew out of the sail. The 30-packs of Budweiser remained safely stowed below, like ballast.

On the way to Nantucket, there wasn’t enough wind—one guy got out briefly and swam—but on the way back, it blew like stink. Slick struggled with the helm in big seas. All these years later, I can still hear the groaning, creaking noises from the old wooden tiller, which steers the boat and for which we carried no replacement.

After that, Slick and I went back with Rocket Man, who won several trophies over the years. After Rocket Man moved to Hawaii, I hitched a ride on a stinkpot, as sailors derisively term motorboats. It was a friend’s Hatteras—big and broad and comfortable with beds instead of berths, a refrigerator instead of coolers, even a shower.

It was a new level of unearned luxury for me, but I soon learned that even swell motorboats present opportunity for public humiliation.

Eager to demonstrate my veteran seamanship, as we eased into the Boat Basin in Nantucket Harbor, I grabbed a stern line and hopped up, balancing on the narrow transom, ready to assist the docking procedure. But then the captain bumped the throttles at the worst moment and I fell in. Splash! Hat over teakettle.

As I climbed the slimy ladder to the pier, what seemed like thousands of people laughed and cheered from Nantucket’s dockside bars and restaurants.

Photo by Blake Jackson

The boat safely docked, I joined the celebration erupting all around us. This might be my favorite time of the whole weekend. The people-watching is nonpareil.

The rest of Saturday and all of Sunday is an open-air festival that is equal parts boat show, Mardi Gras and rock concert. Crews party on the decks of the boats, beer flows—from cans, because only an amateur brings glass bottles or bananas on boats, or whistles once aboard—and the afternoon becomes a pastel-clad, glad-handing procession of genial wanderings. Invitations on board become as casual as the wave of an arm.

By sundown, things are getting loud, funky and fun, and then they open the big party tent. Soon the drink lines are 10 deep, the band is rocking, and it’s a life-in-your-hands adventure out on the drink-slick dance floor.

There’s no racing on Sunday, when they present first a joke-telling session, the awards ceremony, and then a big clambake in the tent.

Like the Figawi itself, the joke session started informally when one race legend, the late Jeffrey Foster, ran aground in Nantucket Harbor. It became part of the weekend, moved into the tent and has been hosted for years now by a goodtime prankster troupe who call themselves the Band of Angels. They bill the event as a “champagne brunch, you bring the brunch.” It is a raucous and decidedly off-color event—50 shades of inappropriate.

After they sweep out the lobster and clam shells, the tent reopens for another bacchanal, traditionally topped at the end of the night as the band breaks into “God Bless America” and everyone sings along in full throat.

Then it’s back to the boats and berths, where sleep is fitful and the sea awaits the morrow.

Photo by Blake Jackson

Rocket Man narrowly avoided that collision, but there were other close scrapes. One time he got cut off and began to shout abuse at the other boat, unperturbed that it was, the Mya, helmed by the late senator Edward M. Kennedy. Bulletproof got sold and would later sink—while tied to a dock!

Slick got a dream job, ultimately living on the same beautiful boat in Nantucket Harbor aboard which he met his future wife (also beautiful).

As for me, I haven’t been on a boat that won anything in years.

But I’ll always go. To see friends you only see on that weekend, for the pastel promenade on Straight Wharf, for watching people in pink whale hats attempt to dance with two drinks in each hand, for the rolling motion of the sea, for the salt and the wind and boozy bonhomie on the docks, for the music and the dancing. I’ll go as long as there’s an open berth.