2026 Annapolis to Bermuda Race: 753 Miles to Bermuda
The Annapolis to Bermuda Race is a 753-mile offshore race that begins with approximately 120 miles down the Chesapeake Bay before turning east for another 630 miles across the Atlantic to Bermuda.
Our race weekend began in Annapolis with the Eastport Yacht Club’s skippers’ briefing. That evening we took Bay Retriever out for one final practice sail before gathering for a crew dinner, watching the sunset over the harbor, and finishing the last of the provisioning. After weeks of preparation, everything was finally ready.
Bay Retriever is a 2019 J/99, one of the newest and smallest boats in the fleet. Although only 33 feet long, the J/99 was designed specifically for offshore racing, with a simple sail plan and equipment built for long passages.
This wasn’t the boat’s first offshore challenge. Bay Retriever had already completed the 2024 Annapolis to Bermuda Race, the 2025 Annapolis to Newport Race, the Around Long Island Race, Block Island Race Week, and thousands of miles of additional offshore sailing.
Our crew of five brought a wide variety of experience. Sean has sailed to Bermuda multiple times and has years of experience as a professional sailing instructor and delivery captain. Ian combined offshore experience with dinghy racing and J/105 sailing. Cameron had sailed nearly every one of Bay Retriever’s 9,000 miles. Jon has extensive Laser experience and time on a J99 as well as completing last year’s Annapolis to Newport Race.
With 13 boats in our class, we knew our biggest competition would come from boats sailing at similar ratings, while several larger boats would likely finish well ahead of us.
FRIDAY
Race morning brought calm conditions and plenty of excitement around Annapolis Harbor. Spectator boats filled the water, the Pride of Baltimore was nearby, and family and friends watched the livestream from home.
Our plan was simple: start conservatively, and sail our own race. Instead, everything came together even better and Bay Retriever won the start at the committee boat end of the line, putting us immediately into clean air and allowing us to choose our own course through the light breeze at the top of the Chesapeake.
The forecast called for light upwind sailing down the Bay before reaching the Atlantic sometime the following afternoon.
As darkness fell on the first day, we were passing Solomons Island and settling into our watch schedule. Sean and I stood the first overnight watch while the rest of the crew tried to find sleep aboard a heeled-over race boat.
SATURDAY
By sunrise we were off the mouth of the Rappahannock River, making good progress south while the breeze held. We knew lighter conditions were expected later in the day, so we took advantage of every bit of wind we could.
Eventually the forecast caught up with us.
Near the mouth of the Chesapeake, the wind faded dramatically. Current became the dominant factor, and progress slowed to a crawl. At one point we even deployed the anchor in an attempt to avoid being swept backward. Whether it fully set or not, it reflected just how little wind remained.
The final miles out of the Bay became a frustrating series of tacks through shifting current and light air. What might normally take far less time stretched into nearly 30 hours before we finally cleared Cape Henry and entered the Atlantic.
Once offshore, the breeze steadily returned. We hoisted the Code 0 as the sun began to set and worked our way through commercial shipping traffic entering and leaving the Chesapeake.
Gradually the constant chatter on VHF radio faded as the shoreline disappeared behind us. The boat settled into a comfortable rhythm, and for the first time it truly felt like we were offshore.
SUNDAY
The wind increased into the 20-knot range, and the seas built quickly as we approached the Gulf Stream. Much of the day was spent reaching under a triple-reefed mainsail and jib, occasionally surfing down waves at speeds approaching 18 knots. The motion below deck became challenging, and not everyone escaped the day feeling their best.
MONDAY
Monday morning began with a squall slowly building on the horizon.
As it approached, we reduced sail until we were carrying only a triple-reefed mainsail. Heavy rain swept over the boat while lightning flashed in the distance. Once the squall passed, it carried the wind away with it, leaving us briefly drifting in light air before the breeze gradually returned. By afternoon we were back under the spinnaker and making good progress once again.
TUESDAY
Tuesday, our final full day at sea, provided the reward after several days of changing conditions. Sunshine, steady breeze, and relatively flat water combined for fast, comfortable sailing toward Bermuda.
That evening the first lights of the island appeared on the horizon. Through the night we watched Bermuda slowly emerge from the darkness beneath a sky full of stars.
WEDNESDAY
Just after dawn, we called into Bermuda Radio who let us know about several cruise ships and the tall ship Sagres entering the harbor.
At 6:51 a.m., Bay Retriever crossed the finish line, completing 753 miles of racing.
After congratulating one another, we lowered the sails and motored around the island toward Hamilton, tying up at the Royal Hamilton Amateur Dinghy Club.
With the race complete, we enjoyed a few drinks dockside before clearing customs, cleaning up, and heading into Hamilton for our first meal ashore. That evening, sleeping in an Airbnb after nearly five days aboard the boat felt especially good.
THURSDAY, FRIDAY
Arriving on Wednesday left us with two full days to enjoy Bermuda before heading home.
We explored the island’s towns, beaches, and historic forts, watched a local parade, sampled plenty of great restaurants, and made sure to try both Dark ‘n Stormies and Rum Swizzles along the way.
SATURDAY
The week concluded with the awards ceremony, dinner, and celebration at the Royal Hamilton Amateur Dinghy Club.
PICTURES | RESULTS | EVENT WEBSITE | TRACKING | VIDEO
