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The Sailing Club, Inc.

Three days of sailing, all promising something different! Eastern shore autumn winds, a night at anchor in a safe creek under a full moon; and the second night will be in the classy Castle Harbor Marina, with nearby restaurants or marina-supplied grilling facilities for your dining pleasure.

We board our boats Friday evening September 16th at Haven Charters in Rock Hall, Maryland. We have reserved two sloops with an eye toward comfort and maneuverability for this weekend under sail. If you arrive early enough you can join the crews for dinner at The Harbor Shack Waterfront Bar and Grill, a Club favorite local seafood eatery.

Saturday morning, after crew briefings and the inevitable last minute provisioning we’ll make our way into the Chesapeake. We'll pick an anchorage based upon the winds and weather outlook. There are many to choose from south of Rock Hall. Crews will anchor and raft the boats with special emphasis on involving any who have never before helped with these tasks. Once rafted, we’ll share the stories of our day over cocktails and a Sailing Club traditional appetizer supper. Be prepared to wander from boat to boat to sample the always ample supplies of food, conversation, and music.

Take a Sunday morning swim, if weather permits, or just enjoy a lazy breakfast. We will have time for some bay sailing before heading into Castle Harbor Marina, four miles south of Love Point on the North Shore of Kent Island at the mouth of the Chester River. Crews can choose to eat dinner aboard, grill and eat at the marina picnic areas or at the nearby restaurants (The Pour House, Cafe Sado) .

Monday morning, if winds are inviting, we can get an early start to enjoy a few hours of sailing before heading on our northward journey back to Rock Hall. Lunch underway will be a good time for all those must-go leftovers! Arriving back at Rock Hall before 3 pm, if everyone pitches in, we can have boats unloaded, refrigerators cleaned out and be homeward bound well before 5 pm.

We’ve reserved two beautiful boats from Haven Harbor Charters in Rock Hall, Maryland. Sign up today – let’s fill them up and go back for more! 

The cost of the trip is $385.00 per person (Skippers - $200.00). The trip price includes charter fees, and one night's slip fee. 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 Mary Ann Gordon 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 $285.00 will be due August 3, 2016. The Club's standard thirty-day cancellation policy applies for this event.

A pre-trip meeting will be held approximately two weeks before the trip, at a time and place to be announced. All participants 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

Mary Ann Gordon
2714 Packer Court
Bridgewater, NJ  08807
Bob Rainey
2006 South Branch Drive
Whitehouse Station, 08889



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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

October Trip

October. 7-9

February 2017

Feb. 2017