An enthusiastic member of Essex Yacht Club, Pequot Yacht Club and the Cruising Club of America, Phil Dickey, MD is a congenial Eastern Connecticut Sailing Association racer who never has trouble finding crew.

“I grew up in Western North Carolina and went to college and medical school at UNC Chapel Hill. I came to Yale for neurosurgical residency, loved Connecticut and stayed,” says Phil, who lives in Guilford. “I started sailing in the late eighties while still a resident. A friend had a J/24 that he and I sailed out of Branford one breezy day, and I was hooked! I was about 28. Growing up in landlocked Western NC, I raced whitewater canoes and kayaks. Oddly, the transition to sailing was straightforward—whitewater and sailing are exciting water sports where competition is a big part of the action.”

“My first sailboat was a thirty-foot Pearson Flyer, Motley Crue. We raced her in the early nineties, mostly in the mid-sound ECSA circuit. She was fast while reaching but slow upwind in light air. Next I owned a C&C 40, Tao, which we raced in the ECSA circuit and at Off Soundings. I owned her from about 1996 to 2002, and she was a fine boat. However, she rolled terribly in a big breeze downwind, and with the arrival of the J/Boats and other designs with wide sterns and more form stability, we became less competitive at Off Soundings. To compete against those newer designs, I bought a Sydney 41, Wahoo. She was very fast, and we did well with her racing at Off Soundings and in the Spring and Fall Series in the Western Sound. We also did reasonably well in the IMS 40 Class in the Western sound—it was a very competitive class until it disbanded with the demise of IMS. I had hoped we could race her to Bermuda, but a couple of my experienced crew thought her bow had too little volume and that I needed a more conventional design for ocean racing. I then sold Wahoo in 2005 (she cleaned up in Lake Michigan) and went boatless for a bit trying to decide what to buy. Finally, a nice Swan 46 Mk 1 came on the market and I bought her in 2011 in Southwest Harbor, Maine.”

Flying Lady (hull #73) was designed by German Frers and built in 1988, and I’m still in contact with octogenarian Señor Frers by email. She’s beamy with substantial overhangs, and she has the tall rig option which helps us in light air. My primary goal was to find a sturdy boat suitable mostly for ocean racing but also for cruising. She’s heavy compared to most of the boats with which we compete, but I’ve never worried about losing the rig or rudder, even in challenging conditions like we experienced in the Gulf Stream in 2012. As we began to understand the boat our racing results improved, and we won the Wetherill Race in 2016 and got 3rd in ORR in the 2017 Marblehead to Halifax Ocean Race. In 2018, after consultation with marine architect Greg Stewart, we decided to update her with a bowsprit and asymmetrical spinnakers. The new configuration makes sailing her much easier and safer for the crew, and I don’t think we have lost performance. We’ve done well, getting 2nd in class in the Stamford Vineyard Race in 2019, winning the 2021 Pequot Yacht Club Faulkner Island Race, and winning the 2022 Wetherill Race. Silver in the Newport Bermuda Race has eluded us…”

“My first and most important sailing mentor was Jonathan Mix, who grew up sailing in Branford,” Phil recalls. “A scholarship football player at the University of Kentucky and a great athlete back in the day, he was one of the most gifted helmsmen I’ve ever seen. He taught me the basics of racing and about tactics and strategy in a handicap fleet. He had such a great sense of humor that we never had trouble getting good crew. Sailboat races were better than a Netflix comedy special. I’ll never forget the night a guest at the Chequit Hotel in Shelter Island mistook him for Dennis Conner (he bore a striking resemblance). Jonathan went on and on about the loss of the Cup and how he got it back in ’87 in Australia. I have never laughed so much. We sailed together for ten years with a crew mostly from the Windjammers Sailing Club, and won a lot of local and Off Soundings races. We had a skilled crew and too many good times to remember. Windjammers John Nevin, Pat Collins and Davey Myers taught me a lot about managing the boat and managing crew. More recently, I’ve learned a ton from Treef Rosow, George Gosselin, Ted Lahey, Rod Clingman, Charlie Reynolds, and other sailors at Pequot Yacht Club in Southport. They’ve taught me the importance of preparing the boat to fit the strengths of the crew, and how to use Expedition and all the information that properly calibrated instruments can provide.”

“I joined Essex Yacht Club in 2014. I brought the boat from Maine to Essex Boat Works at the recommendation of a friend. She needed lots of work, primarily deferred maintenance, and I got a mooring there. Essex Boat Works has taken excellent care of Flying Lady, and I keep her there still. I met North Sails and America’s Cup superstar Tom Whidden in Essex. He had been Commodore at EYC, and encouraged me to join. I pursued membership mostly based upon his recommendation along with that of another Past Commodore, Rob Shickel. The Club has a long history, and recently has agreed to let a group of us promote ocean racing as a priority. We hosted a series of well-attended Ocean Racing Seminars. Next, we resuscitated the ailing Sam Wetherill Race, named after a famed Cruising Club of America founding member, World War I subchaser commander, and EYC Commodore in 1941-42 (when approximately 40% of the members were serving in WW II in some capacity). By 2022, we had eight EYC entries in the Newport Bermuda Race! I am Fleet Surgeon at EYC, and serve on the Sailing Committee.”

`“Ted Lahey, the owner of Essex Boat Works at the time, introduced me to his friends at Pequot YC. I started racing with them on Wednesday nights in 2012, and have been doing it since. They ultimately let me join the Club, despite my landlocked roots and late entry into the sport. I currently split my time between EYC and PYC, though my Flying Lady crew are PYC members. Pequot is an incredible place with a rich tradition (Briggs Cunningham was an early member) and two current Hall of Famers (Dave Perry and Dave Dellenbaugh) as members. The Club emphasizes racing and junior sailor development while maintaining a congenial and welcoming atmosphere.”

“I have skippered four Newport Bermudas, two Marblehead to Halifaxes, and five Wetherills on Flying Lady. I crewed on two other Newport Bermuda Races on another boat. I’ve never regretted being offshore. I just love it, and do it as often as I can. Growing up in western NC, I was surprised to find out how much I enjoyed sailing in the ocean. While you can get hurt or killed, the ocean’s not out to get you. The ocean doesn’t care one way or another about you. She is what she is, she minds her own business, and feels no malice toward you. Truthfully, I think she enjoys having sailors out there enjoying ourselves and entertaining whales and dolphins, with never a turn of a propeller. I find comfort spending time in an environment where nobody’s out to get you. That may sound paranoid, but the IRS, the hospital administrators, and my credit card company can’t find me in the Gulf Stream! Freedom for a few days!”

“In my first Newport Bermuda as skipper (2012), we saw 35+ knots and 20-foot waves in the Gulf Stream. The boat handled wonderfully, and we had a great time. We never worried about the rig or the rudder. During that race the owner of a double-handed boat who was a diabetic became sick, and the Bermuda Rescue authorities tasked us with assisting the boat and that sailor. We had three doctors, a dentist and a fireman onboard, so I guess they thought we were prepared. We came aside and tossed them some saline and the hardware to deliver it, but ultimately the sailor was picked up by a cruise ship as we stood by. We finished the race and were awarded redress by the race committee. On the dock we were met by the evacuated sailor, all better, who made it to Boston on the cruise ship and flew back to Bermuda to thank us in time for our landing!”

“The Wetherill is the perfect spring tune-up race. The course, from Saybrook Outer Light to Gay Head Light and back to Saybrook leaving Block Island to starboard, is approximately 140 nautical miles long and can be completed in approximately 24 hours. Eighty per cent of the sailing’s in the ocean and the weather in late May creates challenges that mimic the Newport Bermuda Race—heavy wind, no wind, and medium wind—all in 24 hours. The Wetherill is the oldest continually run race named after a Cruising Club member, and in the 1950s and ‘60s the cream of the East Coast ocean racing fleet – White Mist, Rhubarb, Reindeer, Loki and Nina – competed in honor of Sam Wetherill.”

“Unfortunately, my family are not sailors,” Phil laments. “They’ll daysail with me on a perfect July or August day with mild breezes and no heel, but I’m the only one with the sailing bug. They all want a powerboat…and you know all sailors are powerboaters – just a question of when!”

My favorite cruising destination is Block Island. It’s easy to get there from Essex and the sailing is frequently sporty, especially in the fall! It’s fun to tie up at Champlin’s, do some paperwork in the morning, get some exercise, get some mudslides, and then try to make it to town or The Oar for dinner. I hope they like me at Champlin’s as much as I like them. Last year I put on a show trying to get off the dock in 30 knots on the nose. With no bow thruster, my 31,000-pound girl doesn’t pirouette in and out of dock spaces, and she doesn’t behave well in tight company. Fortunately I didn’t hit anyone, and to my surprise I didn’t find the performance memorialized on YouTube when I got home.”

“I love Bermuda, with all the activities related to the Race and the spectacular water and beaches. It feels like a Sixties jet set event with all the beautiful boats and people…so much fun. I also really liked sailing into Paradise Island, Nassau. We docked at the Atlantis Paradise Island – very cool. The place has so much energy and beauty, and it’s a little wild.”

“I have a busy neurosurgical practice and I’m Associate Chief of Neurosurgery at Yale New Haven, so there’s not much time for anything other than that and sailing. I’m a member of the Cruising Club of America, and I edit its biannual publication The GAM. It requires a lot of my free time, but it helps me get to know all the nice folks and thoroughly legit sailors who are members of the CCA.”

“The best thing about sailing is that it combines exercise, the water, the outdoors, and competition,” says Phil. “It requires concentration, and you forget about your terrestrial problems when you’re sailing the boat. Nothing is better than moving through the water at 10 degrees of heel with no sound other than the waves and the wind. It’s as close to perfection as you get.” ■

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