There is nothing that I would rather do than go for a boat ride, and I do that almost daily year-round! Taking that ride in areas of the Chesapeake Bay that I don’t normally frequent is even more of a treat. Once a year for the past three years, I’ve been able to do both of the above while benefiting a most worthy cause, such as the CRAB Cup Poker Pursuit.

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CRAB guests and community partner organizations can schedule adaptive fishing excursions about CRAB's new adaptive power catamaran, Dream Catcher. Photo by Will Keyworth

Chesapeake Regional Accessible Boating (CRAB) is an organization started by Don Backe over 30 years ago for which the mission is to provide the therapeutic benefit of sailing to people with disabilities, recovering warriors, and youth from underserved communities. They have a fleet of sailboats that have been modified to accommodate people that could not typically go for a ride on a conventional sailboat. Most recently, they have added a large power catamaran to the fleet and opened a brand-new facility, the Adaptive Boating Center, at 7040 Bembe Beach Rd. which fronts on Back Creek.

Each summer the Eastport Yacht Club (EYC) sponsors a sailing regatta to raise funds that benefit this wonderful organization. This past year a new record was set when over 100 sailboats took part in this regatta on Saturday, August 17. In 2021, a Poker Run was added to the venue in an attempt to encourage powerboaters to participate in this fun and worthy event. Unfortunately, only six to eight powerboaters have participated in each of these poker runs for the past three years. It is my belief that most powerboaters are simply not aware of the event or do not understand that a poker pursuit is a conventional poker run with a twist. After all, we like to get out on the water and party just as much as the sailors do! The number of us that participate every May for the Blue Angels show should prove my point.

During the CRAB poker pursuit, a list of eight to 10 stops is provided in an attempt to allow powerboats of all sizes to participate by choosing stops that are safe and easy. For example, three of the stops in 2024 could be any of the following: Thomas Point Shoal Lighthouse, the central span of the Chesapeake Bay Bridge, Sandy Point Lighthouse, Ego Alley, Spa Creek Bridge (when open), and the Route 50 Bridge, but had to include the new CRAB facility on Back Creek and the Eastport Yacht Club. A “selfie” with five of the above in the background texted to a most wonderful dealer got you your poker hand. You had from 10 a.m. to 3 p.m. to make the stops and then get back to EYC in time for an awesome party under the tent, featuring great food, drinks, and two great bands.

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The CRAB Cup Poker Pursuit allows powerboat skippers to join sailors in a day of fun on the water. Take your boat to designated locations on the Bay and snap a selfie to get your playing hand! Photos courtesy of CRAB

So here is what you missed August 17, 2024:

The weather forecast was for scattered rain, potential thunderstorms, and high winds (great for sailing but not preferred for us powerboaters). The high winds and occasional rain did arrive, but none of the thunderstorms that I could see down the Bay developed in the Annapolis area. It seems to be fascinating to many that I do this poker run with my Jet Ski, but it is a very safe and versatile vessel for handling rough conditions, as long as you don’t mind being wet! 

I launched at Sandy Point State Park, wearing a much-needed drysuit, and headed south for my first stop at Thomas Point Shoal Lighthouse. Holding a CRAB Cup 2024 sign while trying to balance a rocking Jet Ski with the lighthouse in the background with my “flip phone” was more challenging than driving the 15 miles over and sometimes through the three- to five-foot waves created by the 15-mph winds blowing against an outgoing tide. 

With the first stop accomplished I had a really fun “sleigh ride” north running with those aforementioned waves to the much-desired calm waters of Back Creek and the CRAB facility for my second picture stop. Choosing Ego Alley as my third stop prevented me from “catching” the Spa Creek Bridge when it was up, so it was back to relatively rough water traveling against the waves up the Severn River to the Rt 50 bridge. The only consolation was that at that point the sun had come out and provided a much-needed warming effect to my aging body. I decided to take a side trip up the Severn River and gaze at all the magnificent homes that line the shoreline. 

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The author completed the 2025 Poker Pursuit aboard his Jet Ski.

My last stop was at EYC around 1 p.m., giving me enough time to run out into the very rough water again to watch the 100-plus sailboats race across the Bay. The 22-foot CRAB sailboats and their special needs crews were out there with the “big boys” in very rough conditions giving all onboard a thrilling but memorable ride. After following the sailboat race across the Bay, I headed home on another sleigh ride to Sandy Point State Park so I could change into my “party/dancing clothes,” and park my Jet Ski at a friend’s house in order to make the 4 p.m. start of the festivities at EYC.

In total, I traveled 54 miles, spent four-and-a-half hours on the water, and five hours at the land party. I won a trophy cup for the Worst Poker Hand of the day... The best part of the day was hearing that one of the CRAB boat participants mentioned that it was the most distance that they had ever been from their wheelchair.  

Calling all powerboaters! Another CRAB Cup Poker Pursuit will be here before you know it. I believe that we can easily match the number of sailboats that participate in this event to raise money for a very worthy cause. Give yourself a reminder note now to start looking in PropTalk magazine for the August 2025 date, as well as registration information. Let’s show Annapolis that powerboaters love good parties too!! To learn more, visit crabsailing.org/crabcup.

By Dave Nestel