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The Sailing Club, Inc.




Protected waters, great anchorages, gorgeous natural scenery, unique towns and villages,

and a forgiving bottom make the Chesapeake Bay and the Chester River are excellent choices for sailors.

Aerial View of the Chester River Aerial View of the Naval Academy at Annapolis

We’ll board our boats at Haven Harbor Marina in Rock Hall, Maryland, on Thursday afternoon, June 4th and set sail Friday morning for a destination up the Chester River, possibly Langford Creek or the Corsica River. The Chester River is the second longest river on the Eastern Shore and is bordered along much its shoreline by beautiful rolling countryside and lovely estates. By sailing south from Rock Hall and then north up the Chester, we should be able to experience nearly every point of sail on our journey. Once we reach our anchorage and are rafted up, we’ll enjoy an appetizer party and possibly a game of cards before retiring for the evening.

Saturday morning we’ll head back down the Chester and then south on the Chesapeake to Mears Annapolis Marina.  Mears Annapolis is on Back Creek and a short walk to “ego alley” and downtown Annapolis. The marina has many amenities including a swimming pool with pool bar and beautiful restrooms and shower facilities. There are picnic areas with grills as well as several restaurants nearby. The marina also has a complimentary continental breakfast on weekends.

On Sunday, we’ll depart Mears Annapolis for the sail north to Rock Hall. Since we will be keeping the boats for the second cruise, there should be plenty of time to enjoy the Chesapeake on the way, and still get back in time for the new crews to board before dinner.

We’ve reserved two sailboats from Haven Charters – Akula, a 2018 Catalina 425 with 3 cabins and 2 heads, and Sagacity, a 45 foot Beneteau also with 3 cabins and 2 heads.

Akula Sagacity

The cost of this trip is $395.00 per person (Skippers - $213.00 ). The price includes charter fees and one night's slip fees at Herrington Harbor Marina.. Provisioning, fuel, pump-out, and other incidentals are additional and will be handled by each boat's crew. A $100.00 deposit and Release of Liability and Zero Tolerance Form must accompany your reservation form. Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed reservation and release forms, to Eleanor Popolizio at the address below. Reservations will be processed beginning April 4, 2020 with a random draw of those received by that date. All reservations received after that date are on a first-come, first served basis. The balance of $295.00 will be due April 21, 2020. The Club's standard thirty-day cancellation policy applies for this event.

BONUS: Should you sign up for this trip and the Chesapeake II trip immediately following, you will receive a $50 discount on each trip, a total savings of $100.00 (skippers excluded).

A pre-trip meeting will be held approximately two weeks before the trip, at a time and place to be announced. All crewmembers should make every effort to attend in order to meet your crewmates, plan your meals, and make travel plans.

Please note that sailing conditions are dynamic, that your safety, and that of your crewmates, depends on your good physical health and agility.


Trip Leader     

Assistant Trip Leader

Gary Brubaker                    
554 Marietta Ave.
Swarthmore, PA19081                      



The Sailing Club home page

Current Trips

Schedule of our trips

Chesapeake II

Rock Hall, Eastern Bay
Herring Bay, Annapolis, MD
June 5-7, 2020

Day Sail

Bayville, NJ
July 11, 2020


Rock Hall, MD

Victory Chimes

Rockland, ME
August 25-31, 2020

Mallorca, Spain

The Balaeric Islands
September 12-19, 2020


Rock Hall, Baltimore
October 17-19, 2020

Winter Getaway

Tentatively for
Jan 30 - Feb 8, 2021