Sailors Tackle Two Bermuda Races in One Month

A Bermuda Boomerang for the Sailing Crew of Allegiant

Two ocean races in the same month. What can go wrong? Most offshore race crews endeavor to complete one ocean race a year. In 2024, the J/42 Allegiant registered for two Bermuda-bound races: Annapolis to Bermuda (A2B, 753 nautical miles) and Newport to Bermuda (N2B, 635 nm).

allegiant offshore sailing team
James Branson, Hannah Dickmyer, Jordan Hecht, Maryline O'Shea, Albert Bossar, Stuart Proctor, Noah Martin, and Adam Rybczynski: the sailing crew of Allegiant.

Completing this ambitious circuit of 2800 nm would entail about eight race days and 10 days of return deliveries. Allegiant’s skipper Bert Bossar and I, as navigator, were to complete all four legs.

With the starts exactly two weeks apart—A2B on June 7, N2B on June 21—was it even possible to do both? Weather routing confirmed that we could complete A2B in time to start N2B, with a handful of days to clean, re-provision, inspect the boat, and conduct any repairs; as optimistic as we were, we weren’t completely oblivious to the demands we’d be putting on Allegiant.

The second challenge was finding enough crew. Over the years, Bert and co-skipper Maryline O’Shea have surrounded themselves with excellent sailors and supportive friends who have enjoyed sailing Allegiant. From this community, 17 souls stepped up to sail the Bermuda Boomerang.

The third hurdle and possibly the biggest was getting the boat and crew ready to meet the safety requirements for both races. If the tasks weren’t monumental enough, with only five months left, Allegiant’s skippers opted to replace the entire electronics network and instruments on the boat.

maryline onboard allegiant sailing offshore
Co-skipper Maryline O'Shea enjoying life offshore aboard Allegiant.

The Preparation

In winter 2023, Bert poured through the races’ Safety Equipment Requirements (SERs), and constructed a robust to-do list, on top of which were added the annual spring commissioning tasks. Meanwhile, co-skipper Maryline led the electronics replacement program, ultimately choosing Raymarine, whose support during the installation was exceptional. Our friend and “boat doctor” Steve Ormsbee painstakingly stripped the old system and spent more than 80 hours in tight spaces installing the new electronics.

By May 2024, Allegiant was splashed and passed both race safety inspections with flying colors. Not only were the electronics installed, Allegiant also saw her steering rebuilt, her rudder dropped and inspected, and her standing and running rigging checked. A brand-new stove crowned the list of upgrades to the delight of the entire crew.

Attention shifted to crew training. In addition to Safety at Sea seminars and CPR trainings that were attended months earlier, the crew needed to comply with Allegiant’s internal safety protocols and practice the necessary proficiency standards and safety procedures mandated by the races, including communications familiarization, recovering a person overboard, rigging storm sails, deploying a drogue, and other safety-related maneuvers.

The crew spent hundreds of hours studying, sourcing, installing, refitting, repairing, and seeking the wisdom of others. Through the N2B mentorship program, Bert and Maryline were paired with Connie and Mike Cone, owners of the Hinkley Bermuda 40 Actaea. Their guidance and insights from their extensive Bermuda and ocean racing experiences were invaluable.

Allegiant and its crews were finally ready to conquer the ocean and determined to reach Bermuda fast. Twice.

Bert Bossar sailing offshore
Co-skipper Albert Bossar underway in one of two ocean races his sailing team did in June.

Race 1: Annapolis to Bermuda

Allegiant started the Mustang Survival Annapolis Bermuda Race at 1:53 p.m. on Friday, June 7. With our tactician Stuart Proctor at the wheel and the wind on our starboard beam, we executed a near perfect start. We hoisted Big Blue, our largest spinnaker, and made our way down the center of the Bay.

The Bay leg adds the challenge of tidal currents and the reshaping of the gradient wind by the surrounding land. Fortunately, we had perfect conditions for our sail plan, and we exited the Bay second after Aurora, first on corrected time. Our best performance ever for this 120-nm leg.

Next up, the Gulf Stream and the Sargasso Sea. We executed the traditional strategy of heading south and riding the Gulf Stream back up to the rhumb line. Our entry went as planned, and Allegiant reached 12 knots as the current propelled us easterly. The eddies proved challenging as the current models lack accuracy. Passing south of the first one, we rounded the second eddy to the north, picking up valuable positive current from both.

Upon reaching Bermuda, we rounded Kitchen Shoals and sped close-hauled to the finish. We sighted the St. David’s Lighthouse at 291 degrees N on our compass and crossed the imaginary finish line at 5:35 p.m. on June 11, finishing fourth across the line and first overall on corrected time in ORC. Most importantly, Allegiant arrived earlier than projected and suffered no damage or injuries.

Delivery to Newport

After cleaning, re-provisioning, and making a small number of repairs, Allegiant set off for Newport with five crew on the morning of June 15. The conditions looked rougher, with winds forecasted to be against the Gulf Stream current. Fortunately, upon entry the wind dropped, and the crossing went smoothly. We motor-sailed most of the way from the western wall of the Gulf Stream to Newport and docked around 7 a.m. on June 19, greeted by our co-skipper, Maryline, and speed-demon driver, Jordan Stock Hecht, with coffee and breakfast.

hannah racing offshore sailing vessel allegiant
Hannah Dickmyer logged some of her SpinSheet Century Club miles sailing offshore aboard Allegiant.

Race 2: Newport to Bermuda

This was Allegiant’s first Newport to Bermuda Race. The fleet of 162 boats marked a strong contrast to the more casual A2B race (18 competing boats). With the new start line moved up the Narragansett Bay, just off Fort Adams, the excitement and anticipation were palpable!

We set off in very light winds against a strong current at 3:30 p.m. on June 21. Exiting the bay turned out to be a major phase of the race as several small storm cells shut the wind off. As we sailed towards the Gulf Stream, with the wind filling in from the southwest, we held strong within our class. However, we soon noticed our competition was sailing significantly faster: I had misjudged our entry point and should have taken the boat farther west. Allegiant went from third in class to last, a major navigational error.

allegiant sailing crew
James (distant green hat), Marilyne, Tom (red hat), Joshua, and Jessica.

Following a motivational word from our tactician, we switched our focus to passing boats in our class, one by one. We managed to catch all but two of the 11 boats in our class, crossing the finish line third, which corrected to sixth place. We also gained 30-plus places in the St. David’s Lighthouse division to finish 29th out of 99 boats. Not a bad recovery and a testament to the focus of our drivers in a race that was shorter yet more challenging than A2B.

On reaching the dock in Hamilton, Mike and Connie Cone welcomed our skippers with a bottle of champagne, congratulating us on completing the “crazy” Bermuda double in a three-week period.

Delivery to Annapolis

After much needed rest in Bermuda, three fresh crew joined the co-skippers and me for the return to Annapolis. The crossing was relatively benign except for some stormy weather on the second day as we passed through a trough. Predominantly motor-sailing, we crossed the Gulf Stream for the fourth time with almost no wind and glassy seas.

After entering the Chesapeake Bay around 9 a.m. on July 4, our return home was made special by fireworks on both shorelines clearly put on to celebrate our return! When we finally docked Allegiant in the early hours of July 5, we were thrilled to be home. Safe and sound.

bermuda sailboats at dock
What sailor does not dream of doing one of the few offshore races to Bermuda? But most don't dream of doing more than one in a month.

In Closing

Completing two Bermuda races in a month was intense! Though disappointed with the navigational error during N2B, we were proud to have competed in two races with such high-quality competitors. We will be back to compete in the 2026 N2B race.

Most importantly, we were fortunate to have such great friends to sail the various legs and could not have done this without them. Each person was an integral part of this demanding endeavor. We also greatly appreciate the support from our extended Allegiant family.

Lastly, one Bermuda race alone requires a huge investment in boat preparation. Imagine two races! We were extremely lucky to have two co-skippers prepared to take this challenge seriously. The lack of significant breakages and injuries was a testament to the quality of the boat preparation and crew training.

What’s next for Allegiant? We have several ideas in mind, one of them is fielding an all-women’s team in next year’s Annapolis to Newport, followed by Marion to Bermuda or Marblehead to Halifax.

~By James Branson

Find full results in our July issue; find photos here.