The last time John Woods, John Stamos, and John Riley sailed together was over 40 years ago. In 1984, the threesome and their Midshipmen crew campaigned the Navy Frers 46 Vengeance up and down the East Coast, including races in Long Island, NY; Marblehead and Martha’s Vineyard, MA; Portland, ME; and Newport to Bermuda. No doubt the sailing bug had taken hold of the Midshipmen by the end of the summer, but a little thing like US Navy deployments to hot spots around the world and the demands of family life and careers kept the naval officers from reuniting on a sailboat for 40-plus years.
Reunitng for a 333-mile adventure.
Fast forward to 2025 and the famed 333-mile Chicago to Mackinac Race where the threesome joined two other classmates, Hank Gibson and Mark Kalisch, and a “ringer” from the Chicago area, Michael Elam, who rounded out a crew of six aboard Woods’s newly purchased J/105 Exit Strategy.
True to Naval tradition each crew member had his unique moniker: Woods was called “Woodsy;” Riley, “Riles;” Stamos “Famous Stamos;” Gibson, “Hoot;” and Kalish, “Polar Bear.” All are in their early 60s and retired or looking forward to it shortly. Laughter comes easily to the fast friends. One gets the sense this would be a fun boat to take a sail on.
No two Macs are the same
Boat owner Woods says he had always wanted to skipper his own boat in the Mac: “When the J/105 became available, I jumped at the chance to enter my own boat with a bunch of my USNA sailing buddies as crew. Retired Navy Captain Stamos served as co-skipper on the boat. It was a bucket list kind of thing. Even though this race was a slow slough, it was an experience well worth the trouble.”
The former Middies took off in intermittent rain around noon on July 19. They crossed the finish line at 4 a.m. on July 22, two days and 16 hours later, cold, tired, and ready for a hot meal and a shower.
Chicagoan Elam could count over 30 Macs to his credit. This was Woods’s third Mac, his first as owner skipper. Stamos, Gibson, Riley, and Kalisch were making their inaugural run up the lake.
This year’s Mac reminded competitors that no two “Mac Races” are ever the same, delivering the kind of dynamic challenge that has made it an iconic offshore race and a fixture on every sailor’s bucket list.
Known as America’s Offshore Challenge, the 2025 Mac Race tested sailors’ tactical instincts, patience, and mental endurance over the 333-mile course up Lake Michigan and into Lake Huron for the finish at Mackinac Island.
This year’s race coincided with the Chicago Yacht Club’s 150th anniversary, bringing both tradition and forward momentum. With 285 entries—the largest fleet in recent years—the race marked its growth with several innovations, including the debut of the Skyline Sprint (a new spectator-friendly course feature near Chicago’s shoreline), an expanded First-Timers Program ushering in the next generation of offshore sailors, and the return of the Multihull Division.
A rocky start
Unpredictable wind conditions made this year’s race especially demanding, with many boats taking longer than usual to reach the finish. On average this year, it took cruising division competitors approximately 68 hours to complete and the racing division 57 hours. In contrast, last year’s race was one for the record books as Maverick broke the 22-year-old monohull record (just over 22 hours). The former midshipmen completed the race in a little over two days and 16 hours. They finished 80th overall in the Mackinac Trophy Division and were 13th out of 18 J/105s.
Exit Strategy got off to a rocky start as the crew took some time familiarizing itself with the peculiarities of the boat, even heading off in the wrong direction at one point.
“We finally got it together,” an embarrassed Woods confessed. “The first time we sailed the boat together was a couple of days before the race. (We) definitely could have spent more time learning how to sail her.”
Before the starting gun, Woods said, “There are two kinds of Mac racers: the guys who want to go all out to win and the guys like us who want to learn about the race, finish safely, and have a good time… although ask me again in a couple of days if going without sleep for a couple of days is worth it!?”
Because of their limited experience with the boat, the crew’s sail plan was pretty straight forward: minimal sail changes and a constant eye on the conditions to take advantage of any little shift in the wind. Despite their conservative plan, the boat did manage to hit nine knots for a stretch; although the doldrums did see the boat making zero progress for long stretches of time when it seemed they were almost going backwards.
Woods, Riley, Gibson, and Stamos all served the Navy as fighter pilots and/or flight officers. “Speed is how we defined our time in the Navy. This race was all about patience and timing,” said Woods. “Get it right, and you’ll make good time. Miss it, and it’s pretty boring.”
While on active duty, Woods, Riley, and Stamos saw plenty of action in the Gulf War and the western Pacific. No strangers to high level maneuvers, the Exit Strategy crew have logged over 10,000 flight hours on Naval aircraft and have completed almost 2000 (successful!) carrier landings. Woods flies commercially for a US airline while Gibson flies for an investment group.
The Naval aviators aboard Exit Strategy recalled the famous quote from the film “Top Gun Maverick” when Tom Cruise’s character Pete Mitchell turns to his girlfriend Penny who is trying to teach him how to sail her own J/125 and calmly says,“I don’t know how to sail boats, Penny. I land on them.”
Pretty good sailors after all
After their rocky start, the crew settled in for a long run up the lake. The trip was uneventful; with the exception of John Woods losing his phone overboard just as Exit Strategy came under the Mackinac Bridge.
The skipper says, “The sight of the sun coming up and the new moon rising over the Grand Hotel made up for all the little inconsistencies we faced on the trip. By the end of the trip, we had it going. We got to thinking maybe we are pretty good sailors after all.”
The crew was met at the dock by their loyal support team of wives, Bitsy Woods, Tanya Stamos, Susan Riley, Lisa Gibson, and Laura Kalisch with welcoming hugs and kisses. “Any sailor worth his salt has a girl in every port,” laughed Woods. “These girls are pretty special.”
If the group had it all to do over again, “We would have spent more time learning the boat, and we would have packed something better than MREs and power bars to eat,” says Woods. “You’d think that with over 70 years of combined naval shipboard experience we should have figured out how to eat better on the water.”
Will we see Exit Strategy on the start line at next year’s Mac? “Maybe so,” says Woods, “although we’ll make a couple of changes so the trip is more enjoyable.”
By Craig Ligibel
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