© Billy Black

An accomplished offshore racer and navigator, Ed Cesare has completed five of the World’s Great 600-Milers.

“I started sailing aboard our family’s Rhodes 19 along with brother Ben [our intrepid Publisher],” says Ed, who grew up in Norwalk, Connecticut. “The four of us would overnight with a boom tent and air mattresses on the cockpit sole. Later, my parents traded the Rhodes for a Menemsha 24 – sort of a Friendship Sloop copy. This boat had a small cabin, with a head! Mom and Dad got the forward V-berth. Ben was an ‘active’ sleeper so for safety’s sake got the quarter berth. I was still on deck sleeping in the cockpit.”

“One reason I took to sailing was the ‘routine of the ship’ – squaring away on and off the anchor, cooking, getting underway, making colors, etc. And we had great traditions. For example, each year Dad would get an old ammo box; we would put stuff it in and then bury it like we were pirates. We’d use the boat’s box compass to take bearings on landmarks and draw a treasure map. Next season we would return to dig up the treasure! How cool is that?”

“The fleet grew when we purchased a Cape Dory 10 for rowing and sailing. We could field two sets of oars, so in the winter we’d set out with Ben and me on the oars and Dad as coxswain from the aftermost seat. We’d bring along provisions and land on various little islands for lunch. In the summer the Cape Dory was rigged for sail. The boat was a less than ideal trainer – super tender. She was pretty fast and overbuilt, so unforgiving to contact with the Menemsha, docks, etc.”

“Maybe my favorite memory of family sailing was the delivery trips Ben and I made to get Phoebe Snow (the Menemsha) to the east so Mom and Dad could start their vacation in prime cruising grounds. Ben and I were maybe 12 and 15 respectively, and though nothing of taking off from Norwalk for either Mystic or Newport, sailing overnight to arrive the next day. Those trips built independence, piloting skills, voyage planning for tides, etc., and instilled a real love for the marine environment.”

“I’ve had a long series of mentors who have given me opportunities and from whom I’ve learned so much. One has to be Bob Burns, a teacher of mine that campaigned a Ranger 26 back in the mid-‘70s, the glory days of MORC. I totally oversold my skills to get Bob to ship me as foredeck for innumerable day races and Stratford Shoals overnights. Via Bob’s patience and my stick-to-it-iveness, my actual skills eventually caught up with the marketing.”

“Next would be the late Biff Bowker, longtime Master of Mystic Seaport Museum’s schooner Brilliant. Biff was skipper when I participated in Mystic’s youth programs aboard the boat and when I was fortunate enough to ship as race crew during college. The most important thing I learned from Captain Bowker? Do not leave loose personal gear below decks. Aboard Brilliant, if you did, it went over the side.”

“Shellman Brown was a customer of Hathaway, Reiser & Raymond when I worked there during and right after college. He owned a Freedom 40 cat-ketch called Long Reach (get it?). I did a number of Annapolis to Newport and Marblehead to Halifax races with Shellman and he gave me a chance to navigate back from one of the former. That was before GPS, so I became proficient with LORAN and adequate at celestial.”

“I’ve been privileged to crew for Larry Huntington in a couple of his Snow Lions. One will not meet a more accomplished mariner, leader and thorough gentleman than Larry. Larry asked me to navigate for him in the 2003 Transatlantic Race from Newport to Germany. We finished reasonably well, but let’s just say that trip, my first transatlantic and perhaps Larry’s fifth, did not go according to either of our expectations! We wound up doing two more Transatlantics and a couple Fastnets together.”

For several years, Ed (pictured at the helm of Class40 #39 Pleiad Racing in The Atlantic Cup) owned and campaigned the boat on the doublehanded race circuit, mostly with co-skipper Chad Corning. “I got into Class40 because I wanted to do my own program,” he explains, “and having spent a lot of time at the chart table (or hiking off the back of the boat with a tablet) I wanted to restore my once-respectable boat handling skills.”

“I did three Atlantic Cups, two with Chad. We just jelled and it was really hard to find a co-skipper with whom it was as much fun. In addition to our shared, somewhat stylized, sense of humor, we have very complementary skill sets and share a real respect for and love of being in the ocean. Of course we had to deliver the boat from Newport to Charleston in early May to get the whole thing started! The campaign was a great experience. Highlights include laying on our side for fully fifteen minutes in a Gulf Stream squall; spending well over two hours trying to finish Leg 1 at The Battery in New York with zero wind and a vicious ebb current in the Hudson, and winning the Inshore Leg of the 2015 Atlantic Cup and taking third overall.”

“I really enjoyed doublehanding, but at heart I’m a team guy. I like having a bunch of shipmates to work with, learn from, and laugh with. Today the Five Great 600-Milers are the Rolex Fastnet, Rolex Sydney to Hobart, Rolex Middle Sea, Newport Bermuda, and the Caribbean 600. I’ve been lucky enough to do them all at least once: sixteen Bermudas (apart from a couple Marion to Bermudas and Annapolis to Bermudas), four Fastnets, five 600s, two Hobarts and one Middle Sea. I should say that the new ones, the Aegean and Baltic 600s, are certainly vying for a spot on the list. I have not done either of those, and there are plenty of holes in my resumé.”

“I do more sailing than I really should,” Ed chuckles, “juggling that with my non-profit work and continuing professional interests in the venture space – specifically opportunities in the blue economy. But I regularly navigate for three teams. I’ve sailed with Ron O’Hanley’s Cookson 50 Privateer since 2013. I also navigate for Kent Haeger in his Gunboat 62 Mach Schnell and for Tom Bowler in his Morris Ocean 46 Escapade II. This is a pretty interesting array of different boats. I’m looking forward to doing the Caribbean 600 in February with Dan Litchfield in his 1970 Aage Nielsen-designed Hound. Dan and I were Transatlantic shipmates in 2003.”

Ed is an ardent promoter of the Collegiate Offshore Sailing Circuit (COSC). “The COSC was conceived and founded by Rich Wilson. I serve on the Board, representing the Storm Trysail Club, which has been helpful in moving the project along in several ways. We are a very active board, organizing and running the program with no professional staff. Rich is the only American to have finished the Vendée Globe, which he has done twice. I’ve learned firsthand what we all should know intuitively: that you do not race around the world by yourself without being persistent!”

“Rich’s original idea was to leverage the retirement of the Figaro 2 fleet (for the Figaro 3) and source boats to bring to the States to establish a true offshore discipline among the collegiate sailing teams. A variety of headwinds have slowed our ability to achieve this piece of the mission, but we are beginning to really hit stride with an expansion of the focus to include community sailing organizations. Sail Maine in Portland, Courageous Sailing in Boston and Community Sailing in New Bedford all operated two boats each this past summer, competing in offshore races such as the Monhegan Island Race, the Whaler’s Race, the Salty 100 and the Vineyard Race.”

“The stories, pictures, and video we have gotten off the boats this summer are simply gratifying. Thanks to the COSC, its donors and the hard and skilled work of our partner organizations, we are bringing the enjoyment and life lessons of being offshore to a growing group of non-traditional sailors. The looks on their faces say it all. As Rich says, ‘you never forget your first night at sea.’ I urge everyone to check it out at cosc-usa.org. Next year will be important for COSC as we modify our original college-based operating plan to keep the boats in great condition for community sailing organizations.”

“This October was the twentieth year that Storm Trysail and Larchmont Yacht Club have co-organized the Intercollegiate Offshore Regatta, which was founded by The Corinthians. It has grown to be one of STC’s two signature events, and we deploy more volunteers on the IOR than we do for Block Island Race Week! The IOR is hugely popular. After two years off the water – first due to COVID and then due to weather – we had perfect conditions for thirty-four teams from twenty-eight schools. Past Commodore Butch Ulmer and his combined STC/LYC Race Committee got off seven spectacular races.”

“The event really does give collegiate sailors a taste of what big boat sailing is all about, and they love it. One thing I found particularly refreshing this year was how appreciative the kids were. They were all over themselves to thank us – great to see. A particular feature of the IOR is that all of the boats are donated by their owners, many but not all of whom are Storm Trysail members. I think this generosity reflects the fact that owners know we need to work to grow the sport and keep kids in sailing for a lifetime.”

“Norwalk Yacht Club is my home club, and our family is pretty involved there. I served as Commodore from 2017 to 2019. My son Nick is a third-generation member, and chairs the Ideal 18 Committee. Along the way, I too served as Ideal 18 Chair, with stints as Chair of Frostbiting, Regatta, and Junior Sailing. Serving as Commodore was certainly made easier by all of that experience and having grown up at the club.”

“Shellman Brown proposed me for membership in Storm Trysail in 1993. After serving a couple terms as a Governor, I was elected to Rear Commodore in 2017 and will finish my term as Commodore this January. For a club without a clubhouse there are a lot of moving parts to Storm Trysail. There is of course Block Island Race Week presented by Margaritaville, which is traditionally chaired by the Vice Commodore. We have twelve stations around the country, each with a Station Captain. In conjunction with the Storm Trysail Foundation, we originated the hands-on Safety at Sea Seminars that include on-the-water training, presenting these events for both adult and junior sailors around the country.”

“I was introduced to my wife Christine by my college sailing crew, and she’s been hugely supportive of my sailing ever since. Folks ask if Chris likes to sail and I always reply truthfully, ‘Yes but only below latitude 25.’ We love chartering in the Caribbean with the BVI as our favorite destination.”

“I’m grateful to have an avocation as fulfilling as sailing,” Ed reflects. “It’s a lifetime of challenges, experiences, friendships, and the development of skills. I’m delighted to give back to the sport, and love to help build organizations and create connections between people. Sailing is more than a sport. It’s a worldview. It combines the physical, intellectual, and spiritual components of life.” ■