About the Fleet

With over 30 boats, Fleet 5 is one of the most active one-design classes in Annapolis.  Our purpose is: to promote the continued enjoyment of Harbor 20 Class Yachts in fair, Corinthian, one-design racing, and in day sailing and other social activities; to promote friendship among owners and crews; and to support charities through fundraising and regatta participation.

In the Spring and Summer, our boats are raced in the competitive AYC Wednesday Night Race series, and through the winter months in the AYC Frostbite Series. In addition, the boats and owners participate in the H20 Fleet 5 Spring and Fall Championship Regattas which decide the Class Champion and selection to participate in the annual East-West Challenge Cup.  The H20 East-West Challenge Cup includes sailors from Annapolis (Fleet 5), Hilton Head (Fleet 3), Charlotte Harbor, FL (Fleet 6), Santa Barbara (Fleet 4), Smith Mountain Lake VA (Fleet 7) (our newest fleet) and Newport Beach (Fleet 1) and the location rotates annually from west coast to east coast.  Fleet 5 hosted the 2017 East-West Challenge Cup in September with pictures of the spectacular event available on the Gallery page.  The Fleet also supports the Leukemia Cup, CRAB BYBG Regatta, and the Hospice Cup rounding out an active and challenging annual racing schedule.

Frostbite Registrations - First Half November 7- December 12
Register Now and come out for the fun!

Coffee on Thursday
Come join us at the Cafe on Thursday morning to catch up with Fleet 5 News and to hear stories of Fun Races!!!

Fun Race Recap
Our last Fun Race of the fall was Brilliant with mixed weather conditions and costumes that left our jaws dropped and in some cases, jaws open imbibing in glorious concoctions created with only the best and served on the finest silver!

Our famous weatherman, the Italian Stallion, was boggled when sprinkles occurred early in the rigging process. He kept saying, "Only 2% chance" like a chant! With the sprinkles tapering off we launched with the optimism that happy Harbor 20 sailors have- thinking the wind would fill in! While we drifted out to a beautiful morning and the sun came peeking out we all reflected on the gorgeous day and our reflections on the still water.
Our guest PRO, Bill Carty, (we missed the wonderful Mark Kiefaber) made the adventurous decision to start us between 2 mooring balls and race us to SC1 and back. He hailed us by waving the Napoli Soccer Team flag and paying homage to our Neopolitan weatherman.

This proved to be one of the more adventurous races of the season! At one point it was observed that someone was burning incense to find wind direction. That was a new one to me but it smelled wonderful! It was also observed that another competitor was trying to do a penalty turn but we don't really know what that really turned into!

After a wonderful attempt it was decided that we would return to the club and find our way to the mahogany cove. We had a lovely time regaling each other with stories from the race over lunch! Looking forward to more fun in the Spring!

If you are interested in learning more about Harbor 20 Fleet 5 and how you can get in on the fun this year, please send a note to Communications@Harbor20Annapolis.org Thank you!


Crab26