The Sailing Club Logo

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.

We値l board our boats at Haven Harbor Marina in Rock Hall, Maryland, on Sunday afternoon, October 17th and set sail Monday morning for a destination down Chesapeake Bay, possibly Tilghman Creek off the Miles River or Shaw Bay on the Wye River (about 20 miles). On our sail south, we値l pass under the Chesapeake Bay Bridge, pass Annapolis and Thomas Point Light on our starboard side, then turn to port around Bloody Point on the south end of Kent Island. Once we reach our anchorage and are rafted up with the other boat, we値l enjoy an appetizer party and possibly a game of cards before retiring for the evening

Tuesday morning we値l head back out to the Chesapeake and make our way to Herrington Harbour South Marina. Herrington Harbour South is, appropriately enough, at the south end of Herring Bay on the western shore of the Chesapeake. The marina has many amenities including private beaches and picnic areas with grills. There are also two restaurants at the marina, and the small town of Rose Haven is within walking distance.

On Wednesday, we値l depart Herrington Harbour South for a sail north to the Severn River. Once again we will pass Thomas Point Light and Annapolis, this time on our port side, and we値l also get a view of the Naval Academy as we sail up the river. Once up the Severn, there are several excellent anchorages from which to choose

Thursday we値l depart our anchorage for the sail back to Rock Hall and Haven Harbor. Once again, we値l sail under the Bay Bridge, then pass Love Point on our starboard side and sail up Swan Creek to the Haven to fuel up, pump out, and disembark for home.

We致e reserved two Catalina 425s from Haven Charters Dilly Dilly and Cathy Sea. These identical boats have three cabins and two heads.

The cost of this trip is $380.00 per person (Skippers and Trip Leader - $205.00). 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 Gary Brubaker at the address below. Reservations will be processed beginning April 3, 2021 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 $280.00 will be due September 3, 2021. The Club's standard thirty-day cancellation policy applies for this event.

BONUS: Should you sign up for this trip and the Chesapeake I trip immediately preceding, 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                      
Mary Ann Gordon
2714 Packer Court
Bridgewater, NJ 08807



The Sailing Club home page

Current Trips

Schedule of our trips


Rock Hall, MD
June 26-27, 2021

Mallorca, Spain

The Balaeric Islands
September 11-18, 2021

Chesapeake I

Tilghman Island Day
October 15-17, 2021

Winter Getaway

Someplace Special