EDITOR’S NOTE: This is the third installment of a three-part series chronicling the history of Block Island Race Week. Part 3 looks at the last ten editions of Block Island Race Week from 2005 through 2023. 

2023 marks the 30th edition of Block Island Race Week. It’s a momentous milestone, one that will be commemorated by one of the largest turnouts in recent years. A total of 177 boats in 18 classes on three racing circles will compete in Block Island Race Week 2023, presented by Margaritaville. Organizers with Storm Trysail Club have worked hard to build the numbers back up and regatta chairman Andrew Weiss is pleased with the results. “This will be the largest Block Island Race Week in more than 10 years,” Weiss said proudly. “We’ve been working hard on this year’s regatta ever since the 2021 event ended and are very pleased to see the sailors respond in such a positive fashion.” 

One initiative aimed at increasing participation involves the creation of a Performance Cruising Division. It has been hugely successful, evidenced by the fact there will be 57 boats in four Performance Cruising classes. 

A big attraction of the Performance Cruising Division is the fact those classes are all limited to one race per day. It reduces the stress on the water and provides more time ashore for enjoying historic Block Island. 

“That Performance Cruising area has proven very popular and has doubled in the last few editions,” Weiss said. “We are trying really hard to be inclusive. We have a lot of teams coming for the first time in 2023.” 

This edition of Block Island Race Week marks the debut of limitations on the number of professional sailors allowed to compete in some classes. Performance Cruising entries are allowed just one Group 3 on the crew with the number increasing depending on various metrics. There is an open class with no limits on pro sailors as well. 

For instance, a 40-footer with a crew of 10 can have two pros with other categories allowing for three or four. Specifics about the new rules involving professionals were spelled out in the Notice of Race. 

“We’re trying to make Race Week fun for families and not necessarily a fully pro event,” said Weiss, who serves as Race Chair and Vice Commodore of Storm Trysail Club per tradition. “We wanted to level the playing field so the family team had a chance to win the regatta.” 

Weiss noted that every decision he’s made as Regatta Chair has come from the point of view of a sailor. That makes sense since the Mamaroneck, New York resident has been coming to Block Island Race Week since 1975. 

Back then, Weiss crewed aboard Christopher Dragon, an Erickson 39 skippered by his father. Stephen Weiss had a passion for Block Island Race Week and it was passed down to his two sons. 

“I was 14 years old the first time I went to Block Island. It was my father, my brother and my father’s friends on the boat,” Andrew Weiss said. “It’s always been a family tradition to go to Block Island Race Week. Our crew has always been friends and family and it is a very close-knit group.” 

Stephen Weiss passed away in 2002 and Andrew took over the Christopher Dragon program two years later. He has competed at every Block Island Race Week except one since 2005 and done quite well whether racing a J/130, J/122, Sydney 43 or Ker 40. 

There have been a total of 12 different Christopher Dragon designs and Weiss said the latest, an Italia 11.98, may be his favorite. “I’ve told everyone that this is my last race boat. It has been so much fun to sail,” he said.

Linda Weiss will skipper Christopher Dragon in the 13-boat ORC 3 class this year so her husband can focus on regatta management. 

Christopher Dragon has captured class honors at Block Island Race Week five times over the years and Weiss will never forget the 2015 edition when the Sydney 43 finished first or second in all 11 races on the way to topping IRC 2. 

Planning for the 2021 edition of Block Island Race Week was extremely difficult due to the pandemic. Weiss said Storm Trysail Club wasn’t even sure it would hold the regatta before pulling it together in a short period of time. 

Planning and preparation for this year’s regatta has been far more extensive with Weiss, executive director Whitney Simon and other Storm Trysail Club officials making multiple trips to Block Island. 

The Oar served as Race Week headquarters for decades and was a gracious host but when Champlin’s Marina was sold in 2021, it was a better alignment for all the needs of the entities to move back to where it all began. TPG Marinas was enthusiastic about the idea and Champlin’s agreed to berth boats competing in Block Island Race Week at a reduced rate. As a result, a whopping 110 boats will dock at the marina. 

Champlin’s has a permanent tent with an astroturf and stage that fits a few hundred people, which is perfect for post-race parties. Storm Trysail Club has rented two cottages on the property for Race Headquarters. There will be multiple vendors located along the pedestrian walkway as sailors come off the dock and many of the regatta sponsors such as Team One Newport, Helly Hansen, North Sails and New England Ropes will have booths. 

“We have the entire resort, including the swimming pool and recreation areas from Saturday to Saturday. It makes for more of a race village atmosphere, which is what we wanted,” Weiss said. 

Champlin’s served as Block Island Race Week headquarters from the inaugural event in 1965 well into the 1980s and Weiss is glad to see the regatta return to its roots. He was grateful to the many loyal sponsors who have kept the regatta going strong for 30 editions. Sponsors range in business size and support.

“This is one of the last true race weeks still remaining in the United States,” Weiss said. “We think the competition at Block Island Race Week is the best on the East Coast every two years. The Round the Island Race is iconic, which is why we make sure it is held in the best wind conditions of the week.” 

Weiss joined the Storm Trysail Club Board of Governors in 2018 when Commodore Ed Cesare announced during the annual meeting that Rolex would not renew its title sponsorship agreement with Block Island Race Week. 

Weiss is a principal Flintlock Construction Services and AC Developers, which at the time was building a Margaritaville in Times Square. He and others with Storm Trysail Club felt it was time to bring back the fun factor to Race Week and what better way to do so than by partnering with Margaritaville. 

Weiss met with John Cohlan, CEO of Margaritaville Holdings. Jimmy Buffett and has been a longtime sailing enthusiast, loved the idea of sponsoring such a renowned, historic sailing regatta. 

“Jimmy’s interest in sailing made Margaritaville interested in Block Island Race Week. We struck an agreement and Margaritaville came aboard in 2019 and has really been an incredible partner. They know how to bring a fun atmosphere and happening affair with Land Shark beer, games and music.” 

Impetuous is synonymous with Block 

Paul Zabetakis grew up in Pittsburgh and started sailing when he was in his twenties. He was a post-graduate fellow at Yale and spotted a notice on a campus bulletin board: If you want to learn how to sail, come down to the Yale Sailing Center. 

“We went out on the water in a 420 and learned all the basics. How to tack and gybe, how to right the boat after a capsize and so on,” he said. 

Dr. Zabetakis began racing on Long Island Sound aboard a J/24 and also raced an Ensign out of Larchmont Yacht Club. He eventually decided it was time to buy a racer and found a Frers 33 at the Stamford Boat Show. 

That was the first Impetuous and Zabetakis brought it to Block Island Race Week in 1987. He’s been coming back ever since and has also campaigned a Mumm 36, Farr 40 and Swan 42. 

“I’ve been sailing with the same crew for 35 years. When I first bought the Frers 33 we were all starting our careers. We worked on the boat together and learned to sail together,” said Dr. Zabetakis, a nephrologist who operated a dialysis unit at Lenox Hill Hospital in New York City from 1977 to 2000. He was a senior executive with Fresenius Medical Care from 2000 to 2018. 

This year, Zabetakis will be doing Block Island Race Week with Bill Rusconi, Eric Johnson, Cathy Cotell, Sean Cahill, Rob Brodsky and Bill Hajko, all of whom have been crewing aboard Impetuous for more than three decades. Doyle pro-Alex Clegg has been the jib trimmer since 2012, while Casey Brown joined the crew in 2015. 

“I’ve been immensely fortunate to have such really good people sailing with me,” said Zabetakis, current commodore of New York Yacht Club. “It is a true team effort and everyone pitches in to help prepare for Block Island Race Week.” 

The Impetuous team picked up its first class victory in 1999 with the Mumm 36 with Rusconi calling tactics and “we were all ecstatic,” said Zabetakis, who keeps a team photo from that year on his desk. 

Impetuous topped the Swan 42 one-design class in 2015, posting a podium finish in 10 of 11 races. “We have learned an awful lot about racing on Block Island Sound over the years. We have taken meticulous notes about the currents and other unique conditions,” Zabetakis said. 

“We learned one key factor about the Round the Island Race. After you come around 1BI, as soon as you see the dump it’s time to tack and get into inshore.”

Zabetakis would deliver his boat overnight from Larchmont Yacht Club and was always struck by how remote Block Island seemed even though it is located only nine miles south of the Rhode Island mainland. 

“You’d get there and feel like you were in another country,” he said. “It’s all about the novelty of being out on Block Island, which is very unique. You feel like you are away from it all.” The Impetuous crew house was on Corn Neck Road for years, but in 2003 Zabetakis began renting a property near the Southeast Lighthouse. It is always the 10 or 11 crew members as no one brings their significant other. 

“What I remember most about Block Island is enjoying being together with friends. There is great camaraderie among my crew and this is our favorite regatta,” Zabetakis said. “We have the same jokes, same laughs and same fun; only difference is instead of going to bed at 11, we go to bed at 9. 

Impetuous berthed at Champlin’s for many years before moving to the Boat Basin. Mudslides at The Oar following racing was a daily routine, then back to the house for a dinner of fresh fish, lobsters or steamer clams. 

“I think the Storm Trysail Club does an incredible job with this regatta. It’s a very loyal, dedicated group of volunteers,” said Zabetakis, who moved from Larchmont to Jamestown in 2003. “I’ll be 76 this year and I’m pretty healthy. I hope I have many more Block Island Race Weeks in me. As soon as each regatta ends, I begin looking forward to the next one.” 

All we do is win 

Block Island Race Week has seen some dominant racing programs over the past 20 years. None more so than Hustler, a J/29 owned by John Esposito of Mohegan Lake, New York. Hustler captured class honors at Block Island Race Week a total of 18 times, including 11 in a row from 1997 to 2017. Along the way, the brash bunch from Long Island sometimes rubbed competitors the wrong way. 

“We may have been a bit loud and proud. We were always winning and every other boat in the class was gunning for us,” Esposito said. “We were kind of like the New York Yankees of sailing — the team everyone loves to hate.” 

John Esposito first came to Block Island Race Week in 1993 as crew for his father. Tony Esposito brought both a Tartan 30 and J/34 to the regatta and had some success. Father and son bought the J/29 in 1991 and the rest, as they say, is history. 

Hustler lived up to its name by displaying tremendous speed both upwind and downwind and a talented crew with great chemistry rarely made mistakes. Tony Esposito sailed with his son up until 2013, while Neil Caruso was a backbone member of the program for three decades. Robert Weir was a longtime helmsman and would travel all the way from Australia to do Block Island Race Week in the latter years. 

Tactician Max Lopez started sailing on Hustler at the age of 11. “We had the same five core guys the whole way and always had the boat perfectly prepped,” John Esposito said. “After doing the regatta for so many years, we were very in tune with the conditions off Block Island and understood how critical it was to understand the current.” Block Island Race Week doubled as a family vacation and John Esposito’s kids loved everything about it. They would go to the Coast Guard Station in the afternoon to wave to their father and grandfather as Hustler returned to port. 

“Block Island has been a special place for me since I was 19 years old. Just thinking about the place brings back so many memories of great times with family and friends,” Esposito said. “We would rent a crew house and my mother would come out to take care of us. My wife and kids were there and it was just wonderful.” 

Esposito and his mates knew how to have fun, even during the arduous delivery from City Island Marina to the Great Salt Pond. Esposito would pick up two cases of Corona and a bunch of dry sausage from the Calabria Pork Store on Arthur Avenue in the Bronx, turning the 20-hour journey into an all-day party. 

Hustler did its last Block Island Race Week in 2017 and Esposito sold the boat to a Texas sailor last October. He once calculated that Hustler won 81 percent of its races at the regatta. Hustler won eight races and finished second in the other three in a fleet of 12 earning the Isbrandtsen Overall Perpetual Trophy for second-best overall performance in 2015. He just lost out to the top spot to another dominate boat that year, the J/109 Caminos who won a 25 boat one-design class. (In 2021, the Trophy was rededicated to be the top Corinthian boat.) Esposito still wears the Rolex watch he was presented for that feat. 

Hustler developed many rivalries along the way with Mighty Puffin (J/29, Steve Thurston) and Dirty Harry (J/24, John Lavin) among them. Some competitors felt certain Hustler somehow had an unfair advantage and Esposito recalls one rival measuring his keel in the middle of the night and another demanding to measure the spinnaker pole. 

Jeffrey Willis and the Challenge IV team were a dominant force in J/44 class, winning Block Island Race Week a total of eight times, including six in a row from 2005 through 2015. That streak was snapped in 2017 by the slimmest of margins in 2017 when the regatta doubled as the J/44 North American Championship. 

Kenai, owned by Chris Lewis of Houston, Texas, trailed Challenge IV by four points going into the last race and employed match race tactics to great effect. Kenai won Race 8 while Challenge IV finished fifth, resulting in a tie that favored the Houston boat. 

“I had already sold the boat, so I was hesitant to mix it up with (Lewis),” Willis said. “It was a little disappointing because I wanted to go out on top.” 

Willis credited crew chemistry for the sustained success of Challenge IV. David Willis served as tactician for his father, while Tim and Todd Willis were also part of the team. “One of the key factors was we had pretty much the same crew for the whole run,” Jeffrey Willis said. “We also got really good at boat preparation, tactics and weather. We were always ready to go. I don’t think we had a breakdown during any of those regatta.” Willis made his Block Island Race Week debut in 1967 as crew for Bob Derecktor aboard Wild Goose. He wound up doing the regatta a total of 26 times, one of which came during the second week of his honeymoon. 

“It was foggy, rainy and windy the whole week. I don’t think my wife was too thrilled, but she was a trooper,” said the owner of Willis Marine Center in Huntington, New York. Brad Porter was class champion of either PHRF 1 or 2 five times from 2007 to 2017. What was most remarkable about that feat was that those wins came on two different designs — a Carrera 280 and Evelyn 32. Porter, from Duck Island Yacht Club in Westbrook, Connecticut, had a top-notch helmsman in North Sails professional Todd Berman and a strong team overall. Kevin Carse (headsail trimmer), Bob Weinstein (navigator), Brian Weinstein (pit), Nicholas Porter (foredeck) and Eric Eisensmith (mast) were core members of the crew. “I sail with a very talented team that has been together since 1997. We have a lot of skilled sailors, practice a lot and I regularly buy new sails,” said Porter, who has been coming to Block Island Race Week since 1987.

Porter captured class honors three times with the Carrera 280 and twice with the Evelyn 32, which he totally rebuilt. “The Evelyn was a new challenge and we enjoyed switching it up a bit,” he said. 

Out on the racecourse 

Dick Neville took over as Race Director in 2001, succeeding Peter Reggio as the maestro of all on-water matters. He implemented numerous advancements to make the windward-leeward racing more sophisticated, employing offset marks and gates among other things. 

Neville also made sure the principal race officers on all three circles maintained square courses, which often involved moving marks multiple times. That is no easy feat considering Block Island Sound is 100 feet deep. 

Neville recalled when the late Luiz Kahl, creator of the YachtScoring program, came to Block Island Race Week in 2005 to gather information. Two years later, Block Island Race Week made its debut on YachtScoring and has used that platform ever since. 

“Luiz was very diligent about learning everything about the regatta and wrote the software to suit what we needed,” Neville said. 

At one point, the Race Committee had grown to 70 on-water people with a lot of mark boats running around. Neville noted the resources needed to staff three windward-leeward courses was “enormous.” 

Housing was tight and expensive in 2021 and Neville was asked to reduce the race committee by 50 percent, which led to some difficult decisions. On the bright side, the introduction of MarkSetBots for Block Island Race Week 2021 made it possible to run three circles with fewer people. This year, Neville will utilize a total of 14 of the robotic marks that can be moved electronically. 

Neville remembers in 2017 when Regatta Chairman John Fisher asked him and Nick Langone to take a VIP out on the main committee boat that roams all three circles. It turned out it was none other than famous musician James Taylor, whose son Henry was crewing aboard Temptation/Oakcliff. 

“We were a bit surprised when James Taylor and his wife showed up at the dock,” Neville admitted. “(Taylor) was a low-key guy who was impressed that I could go so close to Temptation prior to the start. He lived in Jamestown for part of the year and is a boater, so I think he enjoyed the experience.” 

Neville believes an important part of the enduring popularity of the regatta is Block Island itself, which is vastly different from Nantucket or Martha’s Vineyard. That’s because the Block Island Conservancy has bought up so much land to stop development. 

“We all love Block Island. It’s a very special place that maintains its charming atmosphere,” Neville said. “As for the regatta, we work very hard to keep the fun factor at the forefront. It certainly helps having sponsors like Margaritaville and Mount Gay Rum.”