Sailing Under the Covid Cloud

The old saying is true: there’s wind under the clouds, and as the Covid storm passed, these sailors went to race.
Two sailors racing a sailboat through waters, and making waves.
Brian Conroy helms the Hood 32 Whirlwind during the 2020 Three Bridge Challenge in Annapolis while his father-in-law, and author, trims the spinnaker. Will Keyworth

It was a sobering moment this past spring as my wife, Janice, and I put away our boat after a pleasant afternoon of sailing off Annapolis, Maryland. We’d just learned that Gov. Larry Hogan had declared that recreational boating was prohibited, starting the following day. The growing restrictions of the early COVID-19 pandemic felt confining already. There was so much confusion with restrictions being imposed on travel, school attendance, sports and workplaces, along with a new concept called “social distancing.” It was all combined to change our fortunate way of life, but if anything, we thought, sailing would be safe, right?

Nope. “Stay ashore” was the new commandment. What a bummer.

Regattas across the United States were canceled, sailing charters fell off the cliff, and boat shows were either postponed or canceled. Similar restrictions were put in place across America. I’d never spent so many days in a row at home, and as weeks passed, I felt a building desire to get back out on the water. When our governor finally lifted the restriction on boating, Chesapeake Bay was suddenly filled with boats. Dealers reported record sales of vessels new and old, large and small, and our freedom to be on the water was restored. The sanity of every sailor was renewed.


The Annapolis YC, which had canceled its busy ­racing schedule, decided to give a simple 12-mile race a try, one that required minimal ­race-­committee personnel. The new event was the brainchild of Kevin Reeds, who came up with the Two Bridge Fiasco race. The name and concept of the race was borrowed from a similarly formatted and long-running event on San Francisco Bay called the Three Bridge Fiasco. There would be no trophies, only bragging rights. Entrants were encouraged to race doublehanded with family members.

Reeds figured he’d get 20 to 30 boats, but he ended up with 133.

“I was flabbergasted by the response,” he told me.


The Sailing Instructions called for a pursuit start, where you cross the starting line based on your handicap time allowance. The starting sequence certainly spread out the fleet. As you might expect, it created quite a logjam at the finish line as the larger boats overtook smaller boats in the fleet.

Using US Sailing’s new Portsmouth Ratings Capability, Reeds said it was quite a challenge to rate a Laser Radial against catboats and a wide variety of other small craft. Ratings guru Bruce Bingman and his wife, Taran Teague, worked hard behind the scenes to bring the Two Bridge Fiasco together. Teague told me afterward that the philosophy was to get ­everybody—from a kiteboarder to a 50-footer—into the race.

Bingham received rating ­assistance from US Sailing’s Nathan Titcomb, who helped them get a Portsmouth number for every boat. He used US Sailing numbers and converted them back into PHRF to establish the starting times. The experience, however, reinforced Bingham’s concern with there being too many handicap rules. “One of the problems these days is that there are too many different numbers,” he told me. “I think yacht clubs need to stop offering so many different rating numbers because it’s just too hard to calculate all the scores.”


When I heard about the race, I entered my Hood 32 sloop, Whirlwind. I’d never raced the boat, but Bingman helped me navigate the process of acquiring a handicap rating, and we were off. I was curious how Whirlwind would perform in what could be the boat’s first and only race.

The race starts were staggered by about an hour, and competitors were allowed to sail the race in either direction. The course started off the US Naval Academy on the Severn River, and you could either head out to the Chesapeake Bay Bridge or up the river to the Severn River Bridge. Most boats chose the Bay-first ­strategy, but one boat that bucked the trend by heading up the river—a high-performance Nacra ­catamaran—ended up winning the race, with bragging rights granted.

We started at our designated time alongside three other boats with the same handicap. On the short beat to the first turning mark, we took a small lead and set our asymmetric spinnaker for a 3.6-mile run to the bridge. The breeze picked up to a brisk 18 knots, and Janice steered while I trimmed the spinnaker. Whirlwind was ­gliding along at 8.5 knots.


The spinnaker douse went reasonably well, and we sailed back upwind. A fleet of Etchells that were well behind on the long run made up ground on the beat. At the next windward mark, we set the spinnaker again and headed up the Severn River. It was going well, but as the wind went progressively light, the trailing boats caught up to us. What a delight it was to see 80 or so boats jammed tightly together on the final milelong sprint to the finish.

We sailed 12 miles in 1 hour, 49 minutes, and finished ninth in our 44-boat class. No official bragging rights for us, of course, but we did OK. Best of all, we had a great sail, and that was the point, right?

A few weeks after the Fiasco, Tred Avon YC in Oxford, Maryland, notified the US Naval Academy that they were unable to host the annual Annapolis to Oxford Race. Varsity Offshore Sailing coach Jahn Tihansky (who won the Fiasco on a ­catamaran) wanted a race that the academy’s midshipmen could compete in, so he helped ­pioneer a new race.

Taking a page from the Annapolis YC’s Fiasco, the academy created an alternative race called the Three Lighthouse Challenge. The course would take the fleet to ­channel markers close to Sandy Shoal Lighthouse, Thomas Point Lighthouse and Bloody Point Lighthouse. The course was 21.6 miles.

I entered Whirlwind for my second race. Bingman and Teague served as race officers for a traditional starting sequence. This time, my ­doublehanded crewmate was our son-in-law, Brian Conroy, who was competing in his first sailboat race. I figured he would be a good downwind ­helmsman. Ninety-five boats crossed the starting line in a brisk 20-knot wind and made a fast trip around the bay. Aboard Whirlwind, we made the passage in 3 hours, 40 minutes, with only 6 of the 21 miles sailed under spinnaker. We missed the podium by 1.7 seconds, but more important, it was another exhilarating day on the water. There was plenty of bragging around the Jobson family dinner table afterward.

As we passed the fleet on ­different legs of the course, I was astounded by how many different types of boats were in the race. The Three Lighthouse Challenge used six different ratings for 13 classes. I look forward to the day when we have one handicap rating rule. In this age of supercomputers, it would seem that goal should be attainable.

While Bingman’s concern is of too many handicap ratings, Reeds is of a different opinion. “We need to embrace different formats to get as many people out on the water as we can,” he said. “We find there are a lot of boats that spend time cruising that might like to do these kinds of races. We need to be more inclusive and more open to doing things in creative ways.”

Navigator-style races are becoming more popular, and these race distances don’t have to be excessive. I think two to five hours in duration is about right. It makes for an interesting day on the water, and you get to see many sights along the way. For us in Annapolis, we rarely race under the imposing Chesapeake Bay Bridge, but there is always some kind of intellectual challenge of passing underneath it. The roadway high above creates wind thermals, and tidal currents swirl around the bridge’s structure. Big gains and losses can take place around bridges.

During our two races on board Whirlwind, I learned a few valuable lessons: Clear sailing lanes are absolutely essential; be ready to shift gears by setting the spinnaker at a moment’s notice; give the crew a long trick on the helm; study the tidal currents; have plenty of food to eat; and don’t worry about the results. Finishing the racecourse is reward enough.