The ALIR through my lens

by: Josh Reisberg (member, Sea Cliff YC / Storm Trysail Club)

As a sailor based in the Western Long Island Sound, two races are on my calendar year after year.  First is Bermuda—in even years, it’s Newport-Bermuda on OPBs (other people’s boats).  In odd years, it’s the Bermuda 1-2, a two-legged race where I race my 40-foot J/120, Abilyn, singlehanded from Newport to Bermuda and doublehanded back.  But second on my list is something much closer to home—a regatta that offers adventure, the longest ocean racing leg among local distance races, and the type of camaraderie and competition that I am accustomed to experiencing during major ocean racing and international events, of which I’ve sailed in many.  That regatta—known as the Around Long Island Regatta or ALIR—should be a staple on the schedule of any sailor in the Mid-Atlantic region or Tri-State area who wants a race that combines inshore and offshore legs in a physically and mentally demanding package.

Sea Cliff Yacht Club on Long Island’s North Shore founded the ALIR in 1977, based on a brief to create an accessible ocean race that would attract sailors of all levels, allowing those who want to accumulate ocean miles the opportunity to do so and allowing those who want challenge and adventure to get their fix.

Originally starting offshore south of Rockaway Point in the Queens borough of New York City, in 2017 the start line moved into NY Harbor, adding a new component to the race.  The new starting location allowed spectators a unique stadium-style vantage of the starting area with the lower Manhattan skyline as the backdrop, while offering competitors the opportunity to race passed arguably the most iconically American monument in the United States, the Statue of Liberty. 

Over the years, the race has attracted weekend cruisers, family boats, and tried-and-tested bluewater racers to challenge the 207-mile course and vie for the coveted ALIR trophy for the best performing boat overall.  In 2010, George David’s Reichel-Pugh-designed 90-foot monohull, Rambler 90 (only 10 feet shorter than Comanche), set the current race record of 15 hours, 42 minutes, 4 seconds.  For the remainder of the fleet, the race can take anywhere from 27 hours to 50+ hours, requiring focus, resolve, determination, and, in some years, unrelenting patience, to complete the course, which can serve up big breeze in one moment but require that you drop anchor in another so that you don’t lose forward progress.  If you’re not ready for anything when you compete in your first ALIR, you’re most certainly prepared the second time. 

THE ADVENTURE

For me, sailboat racing has always been a vehicle for adventure.  My ALIR adventure begins in the weeks leading up to the race and doesn’t end until I’ve crossed the finish line.  At least two weeks out from the race start, I’ll begin preparing my boat and monitoring weather patterns across the Sound and south of Long Island.  I like to race my J/120 light.  Anything that my PHRF rating will allow me to remove, such as the boat’s cushions and saloon table, I remove.  I keep only what I need to race fast and stay safe.  That includes my Winslow 4-man ultralight liferaft (although a life raft is not a required safety item), two tool rolls, ditch bag, basic spare parts, and a case of assorted damage control items that allow me to address any number of foreseeable contingencies on my own.

Analytics: I approach the ALIR as I approach any other ocean race because the ALIR is an ocean race, and one that traverses an actual named ocean.  Although half of the race takes place inside the Long Island Sound, the other half is indisputably offshore.  And even in July, the North Atlantic Ocean can serve up big conditions.  In 2023, for example, the fleet saw 10-foot swells and 30 knots of southwesterly breeze along the south shore, creating for a fast, wet ride passed Fire Island all the way out to Montauk Light.  But even in lighter conditions, I use the ALIR as practice for bigger, offshore races such as the Bermuda 1-2 because I understand that the routines and seamanship necessary to traverse oceans are first developed close to shore.  Any opportunity to be offshore, no matter how far, is an opportunity to test those practices and ensure that seamanship become second nature.

Closer to the race start, I’ll run various routing scenarios using my preferred software, Expedition, which will give me a sense of what an optimal course looks like.  Invariably, however, it’s the sailor with the most experience on these waters that knows Neptune’s secrets.  To succeed in the ALIR, you need to sail it.  And sail it again.  And again.  Only then will you develop the discipline to not let yourself sail a longer course by heading too far offshore, and at the same not be too timid to get close to the breakers off Amagansett in an effort to take advantage of south shore land effects and sail the shortest distance to Montauk Point.

Pure Beauty: But even for those who don’t take such an analytical approach to ocean racing, or regattas in general, the beauty of the landscape over the ALIR course is undeniable and should be experienced by all.  The Thursday start is nothing short of epic.  Between the lower Manhattan skyline, the Statue of Liberty, and the cheers of spectators on the Manhattan Sailing Club’s floating bar, the Willy Wall, competitors are treated to something truly unique, and unlike any local distance sailing event.  After navigating NY Harbor and rounding the SW corner of Queens to begin the offshore leg, sailors pass Coney Island, and, later during daylight hours, Jones Beach, where a concert may welcome the sunset.  At nightfall, the breeze in the ocean consistently drives sailors farther east, with multiple lighthouses guiding their way.  Faster boats will enjoy sunrise on the east end, with some boats rounding Montauk Point (“The End”) in the early hours of Friday morning.  In lighter conditions, for boats sailing closest to rhumb line, the sound of breaking waves is oddly just as peaceful as it is terrifying.

The ride home is no less beautiful.  The openness of Gardiners Bay and the Long Island Sound between Plum Gut and Stratford Shoal is a stark contrast to the confines of our daily lives and offers a welcome opportunity to disconnect and reflect.  And for those like me who are privileged enough to have spent so much time on the waters of the Western Long Island Sound, The Stacks of Northport Power Station, although not necessarily pleasing to the eye, always seem to warm my core, signifying that I’m close to home despite not being able to pass The Stacks for what feels like a half day.  Despite this trickery, the Long Island Sound plays no games with its sunsets.  In clear conditions, I always make sure I’m on watch to experience them as even from 25 miles away, they backlight the Manhattan skyline, bringing the race full circle.

The camaraderie of challenge: But even before I began anticipating the course, I look forward to day before the race when most of the fleet converges on Liberty Landing Marina in New Jersey.  Some come from parts south, such as Atlantic Highlands, NJ, and even Annapolis, MD.  Others come from up the Hudson River.  I come from the western Long Island Sound, which requires that I time my passage to arrive at Hell Gate to catch the southbound current down the East River towards New York Harbor.  No matter how many times I do it, I marvel at the cityscape and appreciate my spot on the water as I watch the northbound traffic on the FDR from less than a 100 yards from the asphalt.  Later during the passage, I text my mom, who lives in Dumbo, Brooklyn, telling her to come down to the waterfront and watch me pass under the Brooklyn Bridge, as ships have been doing for over 140 years (passing under the Brooklyn Bridge, not texting).

Arriving later that day at Liberty Landing Marina, I can immediately feel the energy of the regatta.  Competitors from all over are walking the docks, making their way to the registration desk or the chandlery for last minute supplies, or relaxing with their crews.  After saying hello to more than few familiar faces, I’ll continue with my preparations, double-checking my instruments and rigging the boat.  Then, later that evening, I’ll walk over with my crew to the Captain’s Party, where the Principal Race Officer, Doug Wefer, will give a briefing on the race, and where crews will unwind, talk shop, and experience the camaraderie that binds those about to share in a challenge.    

THE CHALLENGE

The traditional ALIR course takes sailors 207 miles across no less than five different phases of racing.  

The first phase is the harbor race.  After the gun, competitors must dodge commercial traffic and decide which side of the harbor offers the best balance of breeze and current.  The biggest decision comes whether to sail to windward of a moored barge or in its lee while attempting to fetch the Verrazano Narrows Bridge.

The second phase is the ocean phase, where the key strategic question is how far to go offshore.  In lighter, more thermal conditions, being slightly farther offshore can—but doesn’t always—provide more consistent breeze.  In 2024, despite the lighter westerly, the winning tactic was to gybe close to shore and stay as close to rhumb line as possible.  As night and fatigue set in, sailors must fight the urge to “wait another 5 minutes” before gybing back towards shore.  In 2022, I mistakenly took a flyer, failing to gybe on the lifts.  I paid the price by sailing a much longer distance.

The third phase is Gardiners Bay, with Montauk Point serving as its gatekeeper.  Depending on when sailors reach The End of Long Island, sailors can see upwards of 3.5 knots of current. Time and conditions will dictate where sailors must position themselves when entering Gardiners Bay to ensure they don’t get slammed by the steep waves that can stack up when, for example, they’re fighting an adverse, southern-flowing current in a strong southerly breeze.

The fourth phase is Sound re-entry.  When firmly in Gardiners Bay, the key strategic decision is whether to enter the Sound through Plum Gut or the Race.  Plum Gut is the most preferred waypoint because it’s the shortest course from Montauk Point.  But in a northerly breeze, getting to the Connecticut side as fast as possible through the Race could prove to be a winning play.  And of course, there are multiple entry points between the Gut and the Race, with differing levels of gains and losses to be had depending on timing and breeze.  For me, the navigational complexity of the ALIR is, in large part, what makes the race such a rewarding, annual endeavor.

The fifth phase is the Long Island Sound phase.  After passing the tidal barrier marking the entrance to the Sound, competitors must carefully analyze whether to take the Long Island side or the Connecticut side of the race course.  Faster boats will spend most of the day Friday inside the Sound with the fastest boats finishing around sunset.  In 2024, I was the third boat in the fleet to finish, behind only Avalanche, a grand prix Soto 40, and Max, a Pogo 50.  Avalanche finished in daylight with significant thermally-induced breeze still prevalent across the race course, over which no gradient flow existed due to the presence of a high-pressure system overtop the region.  As day became night and land temperature dropped, the thermal breeze dissipated, leaving nothing but illusive zephyrs to connect in order to make forward progress.  Although we were successful at connecting the dots, sailing 3 miles still required 8 hours.  At the start of the second night, the race had transitioned from a test of sail trim and navigational strategy to one of mental fortitude.  Fortunately, my boat is a light-air, upwind weapon, sailing faster than the breeze in sub-5 knot conditions.  We played the game well enough to ghost over the finish line at 0329 Saturday morning and correct over our nearest competitor, a well-sailed J/99 named Thin Man, who was not too far behind.  We celebrated with pizza and a burger at the yacht club.

Boats behind us had similar luck in the pre-dawn hours of Saturday morning, with some giving into their inner demons, choosing to engage the “iron genny” rather than sticking it out (I’ve been in that proverbial boat).  But for those who remained patient, the breeze reemerged during daylight hours, propelling most of the remaining fleet home for a Saturday finish, well in time for the awards barbecue Sunday afternoon on the beach at Sea Cliff Yacht Club.

Although every race is different, what remains consistent are the people—both the racers who are excited to be out there doing what they love and the volunteers at Sea Cliff YC who believe in the race and its continued longevity as something that is synonymous with summer sailing on Long Island Sound.

And then there’s me, who is excited for the Around the Islands (Long and Block) long-course option in 2025. In fact, I’m looking forward to all the new changes that the ALIR committee is implementing—YB trackers, the trophy/prize for best onboard photo, and yes, the long-course option. We all sail for different reasons. And the changes the ALIR committee is making will make the 2025 ALIR worth your time.

See you out on the water.

Josh
josh@abilynsailing.com