Triple Crown of Charity Sailing Update

Three Regattas, One Big Trophy Winner

The three major Annapolis charity sailing races that comprise the qualifiers for the Triple Crown of Charity Sailing Award will happen in a condensed time frame, yet will happen! Here are the latest updates:

Don't we all hike a little harder and happier when the sailing photograher shows up? CRAB Cup 2020 photo by Will Keyworth

First stop was the CRAB Cup, which unfolded August 15 in Annapolis. “The CRAB Cup had 89 boats registered for the pursuit race,” says Chesapeake Region Accessible Boatint (CRAB) executive director Paul “Bo” Bollinger. “Historically many in the fleet have caught up to the CRAB Beneteau First 22As by the first mark, but not this year. The 10- to 12- knot wind from the northeast worked perfectly for the CRAB sailboats on the race across the Bay to the first mark near Kent Island and the second, back across near Whitehall Bay…

“For the first time in the CRAB Cup’s 14-year history, a CRAB sailboat with a disabled skipper at the helm won!” Congratulations, Tim McGee!
Find full result here and SpinSheet’s photos here.  ... and CRAB always welcomes donations here

Next, the Annapolis Leukemia Cup. Originally slated for the end of May, the Leukemia Cup will unfold September 5 off Annapolis. Both social events, the Summer Gala at Annapolis Yacht Club the night before and the post-race Rock the Dock Party at Eastport Yacht Club, are canceled. Find the online auction at Following racing, there will be a virtual awards ceremony. Find a link to it as well as a “donate” link at

The final stop will be the Annapolis Hospice Cup, September 19. You guessed it: the Shore Party will not take place in 2020. The Eastport Kitchen will provide boxed lunches for crews. Following racing, podium finishers may pick up their awards, have their winning crew photo taken, and enjoy a beverage in a socially distanced manner in the back lot at Forward Brewing Company from 6-8 p.m. Find links to buy cool gear, donate, register to race, fundraise, and access the online auction at the user-friendly new website:

Find more racing news here. 

Learn more about the Triple Crown award at