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The Sailing Club, Inc.


If ya don't believe me jus' ask the Midshipmen: Midshipmen's Naptown Funk

This autumn trip combines some of the best Chesapeake Bay sailing conditions with a visit to historic Annapolis, Maryland and - best of all for some sailors - the Annapolis Sailboat Show. We're chartering some of our favorite boats from Haven Charters in Rock Hall, which allows time for some good sailing before reaching port, without the risk of running out of time.

Thursday, October 6
Arrive in Rock Hall and settle aboard the boats. Dinner at one of Rock Hall's seafood restaurants.

Friday, October 7
Depart Rock Hall and sail to Annapolis, which is only about an eighteen mile sail from Rock Hall, so we don't have to go directly there. If conditions are right, a sail on down the Bay to Thomas Point light or further may be in order. However, sailing directly to Annapolis will get us there in time to attend the Sailboat Show late Friday afternoon. We will have slips reserved at a marina within walking distance of town that is served by the Annapolis water taxi.

Saturday, October 8, 2016
Attend the United States Sailboat Show in Annapolis. Since not all of the crew might be interested in attending the Show, Annapolis offers many other activities such as touring the Naval Academy and historic Annapolis, and the Maryland State House. Quiet Waters Park and a number of historic churches are within walking distance of the marina. There are also many restaurants within walking distance.

If one of the skippers and a first mate are interested, one of the boats could go out for a sail for some or all of the day instead of attending the show.

Finally, many of the vendors like The Moorings and Cruising Outpost have parties on the Saturday evening of the show.

Sunday, October 9, 2016
A leisurely return sail to Rock Hall is planned. Again, since it's not a long distance, we can enjoy some classic fall Chesapeake sailing. And since the next day, Monday, is Columbus Day, we may find lighter traffic for the drive home.


The cost of the trip is $425.00 per person (Skippers - $239.00). The trip price includes charter fees, and two nights' slip fees. Fuel, provisioning, 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 Mia McCroskey at the address below. Reservations will be processed beginning April 2, 2016 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 $325.00 will be due August 23, 2016. The Club's standard thirty-day cancellation policy applies for this event.

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

Mia McCroskey
19 Manor House Drive, K-12
Dobbs Ferry, NY 10522               
Gary Brubaker
554 Marietta Ave.
Swarthmore, PA 19081



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Current Trips

Schedule of our trips

OWT Trip

Rock Hall, MD
May 14-15

June Trip

Channel Islands
June 4-12

August Trip

The Solent River
August 12-19

September Trip

Castle Harbor
Sept. 17-19

February 2017

Feb. 2017