The proverb “From small beginnings come great things” aptly describes Quantum Key West Race Week, this year celebrating its 30th anniversary on the turquoise palate surrounding Key West. Innocuously started to help broaden Yachting magazine’s appeal, Race Week grew into the most important regatta in North America and the best winter destination regatta in the world. “This truly is one of the greatest regattas in the world and to me it’s the perfect winter break,” says Terry Hutchinson, who has won Boat of the Week honors twice as a tactician. “It has steadily evolved over the years into an extremely high-level event in all respects.” Being a destination regatta, however, there was no guarantee Key West Race Week would succeed. There is no hometown yacht club aligned with the event or a strong local sailing scene from which to cull entries. Instead, they come from far across the United States and around the world. That Race Week has succeeded through the years is a testament to the many organizers, volunteers and sailors who have returned year after year for challenging racing. Shoreside parties can take a regatta only so far. The great satisfaction after a day of maneuvering a boat around the racecourse in close quarters is what keeps sailors coming back for more, and still lures first-time entrants. “We’ve never raced there before but the regatta’s been on our bucket list for awhile,” says 49-year-old J.D. Hill, of Texas, who’ll be racing his J/122 Second Star for the first time in Key West this year. “We went down a few years back and checked out the 25th anniversary Race Week and said we’ll do this one day. It’s got warm water, which my wife wants, and it’s got good competition, which my crew wants.” Key West Race Week was founded in 1988 by Yachting magazine. Former editor Charlie Barthold, an associate editor when the regatta started, recalls that the magazine was looking to broaden its advertising base. They were running regattas at Whidbey Island in Washington and on Chesapeake Bay at the time, and Key West was a unique draw. “At that time, location-based race weeks were a selling point,” says Barthold, who’s now an executive with worldwide management consulting firm McKinsey & Company. “It was easy to sell people on the idea of Key West in the middle of January; it has ideal winter sailing conditions.” Barthold said the early days were pioneering. “It was unstructured and somewhat chaotic, like running a startup,” Barthold says. “There wasn’t a lot of structure down there at the time. We were working out of trailers and scooping up volunteers everywhere. In the middle of it we’d wonder why we got ourselves into it, but it was a lot of fun. It’s amazing that it has succeeded as long as it has. Building it was the fun part.” In 1993, the magazine contracted Premiere Racing, led by Peter Craig and Jeanne Kleene, to manage the event, and they ushered the regatta through some heady days. Premiere Racing took over full management of the event in 1997 when it purchased the trademark from Yachting and for the next 11 years, through 2008, Key West Race Week averaged 282 entries. The largest fleet of 326 boats occurred in 2001, and the smallest fleet was 256 boats in 1998. “The first year Jeanne and I managed the event (1993) we had a 110-boat regatta,” says Craig. “The next two decades saw great change. It started as a low key PHRF/IMS regatta. To what it became was a big transformation.” A total of 5,662 entries have participated in the previous 29 Key West Race Weeks, an average of 195 boats per year. Through the years, the regatta has showcased what is hot and new in grand-prix racing circles. In the 1990s, IMS was the showcase rule and new boats were often fresh from the builder. The phenomenal growth of offshore one-designs can be traced through Key West Race Week and designs such as the Farr 40, Mumm 30, Melges 24, J/105 and J/70 have fielded marquee classes through the years. The Melges 24 Class holds a unique record: 17 times it was the largest class of the regatta, including 16 consecutive years from 1994 to 2009 when it averaged 53 entries per year. “The sailing conditions are fantastic,” says John Kostecki, who’ll call tactics on the TP 52 Platoon. “Normally you get the chance of good breeze for a part of the regatta, and each day is a new challenge. It’s great winter sailing in the U.S.” Outstanding participation aside, Craig’s proudest moment came in 2002. The 15th anniversary regatta was held four months after the 9/11 terrorist attacks. Watching planes plunging into the World Trade Towers in September 2001 left Craig’s jaw agape and his mind wondering if race week would even take place. It did so, and the 321 entries counts as second-most all time. “The fear after 9/11 was that no one would travel,” says Craig. “But we had pretty much the biggest regatta in 2002. It was sailors saying they were not going to let people dictate where they went or what they do. We pulled together the Melges 24 World Championship on short notice for 71 boats. It was a four-ring circus that year.” In 2015, Premiere Racing stepped aside and passed the baton to the Storm Trysail Club, the national club with nine stations around the United States, which has continued the tradition with generous support from title sponsor Quantum Sails. The Storm Trysail Club is unique in that it has no centrally located clubhouse, but it has extensive experience running events such as Block Island Race Week. Founded in 1965, Block Island Race Week is perhaps America’s original destination regatta. “Key West Race Week is a terrific bookend to the club’s long‐standing Block Island Race Week, which we’ve run for more than 50 years,” says Key West Race Week Race Committee chairman Dick Neville, who has been a regatta officer at Key West since 1999 and also has run Block Island Race Week. “Nearly every event the Club runs is a remote event. We’ve had great experience and success with Block Island, so it wasn’t a foreign endeavor to set up in Key West.” Although the Storm Trysail Club only recently assumed management of Key West Race Week, club members such as Neville have been involved with the regatta for many years, volunteering thousands of hours helping organize and run the event. In fact, the late Bruce Brakenhoff, Sr., was the original race committee chairman and his experience lent instant credibility to the regatta. “Bruce had a lot to do with the early success of Key West Race Week,” says Barthold. “Under Bruce’s leadership the race committee knew what it was doing and was well organized.” Race management has been one of the strongest selling points of Key West Race Week through the years, and the event could be considered a pioneer in that area as well. Since the dawn of sailboat racing, race committees only signaled the racecourses through code flags. It was at Key West Race Week where race committees began using the VHF to communicate with competitors on the racecourse, alerting them to what they were thinking. It marked a big step forward in the race committee-competitor relationship. “What drove me crazy was the lack of communications on the racecourse,” says Craig. “As a competitor, you had no idea what the race committee was thinking. You had to get close to the committee boat to see what flags were flying. We established a set procedure in writing, outlining what race managers were expected to do in communications with the fleet. To this day professional and amateur sailors alike seem to think some things we did have helped raise the level of race management around the world.” After so many years of success, one might think that first-time participants are tapped out, that there’s no serious racer in the United States who hasn’t done Key West Race Week. But that’s not the case. Hill’s Second Star was the first entry for the 30th anniversary race week. His anticipation of good winds and good weather in the Conch Republic is echoed by another first-time entrant, Ian Hill of Virginia. Although he’s of no relation to the Texan, the Virginian Hill was “counting down the days” to Quantum Key West Race Week after winning his class at the Storm Trysail Club’s Annapolis Fall Regatta last October. He says his team is especially fired up and cannot wait to start racing in Key West. “Some of my crew has competed in Key West in previous years, but this is the first time for me and it has been a dream of mine for years,” says Hill. “I regard the regatta as a gold cup event, the Cadillac of regattas for all its elements: the location, time of year, level of competition…all of this. When we watched the videos from 2015, we felt like we were there, so we can’t wait to be part of it ourselves.” —Sean McNeill Note: This story was published in the Quantum Key West Race Week 30th anniversary commemorative program.