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The Sailing Club, Inc.

Chesapeake Bay & Annapolis

Sailing on the Chesapeake Bay in late June is sublime. There are warm, fresh breezes but not the crowds of July. This trip uses a proven Sailing Club trip formula: Great sailing + learning opportunities + good friends + new friends + food + raft-up + potent potables (liquid refreshments) = Supreme Satisfaction.

If you're new to the club or haven't sailed for awhile this three-day trip is just the ticket to refresh or sharpen your skills. Of course, a long weekend sailing trip that includes a night in Annapolis is also a favorite of long time sailors.

Marina Main Building Friday, June 23rd - Crews will make their way to Haven Harbor Marina in Rock Hall, MD using car pools wherever possible. Please remember not to load the boats with your luggage and provisions until your skipper gives approval, as boats must be inspected while empty. Depending on weather, you may plan to arrive early in the day with a bathing suit to enjoy the marina's pool, or explore the area. It is hoped that everyone will arrive by 5 p.m., so that both crews can enjoy dinner at The Harbor Shack at about 7 p.m. Dinner with your crew provides an opportunity to catch-up with old friends or make new ones. We are planning on six per boat.

Saturday, June 24th - Once boats are ready and any last minute provisions are aboard (like ice), we plan to head out to the bay as early as possible to enjoy some good sailing. Prevailing winds in June are forecast to be from the east-northeast and we plan to do a raft-up off a river that evening with the club's traditional appetizer party. The first choice for this trip is the Corsica River, which is off the Chester River and considered a beautiful spot. It is the location of the Russian embassy's dacha (no longer occupied by Russians) and rumored to be the scene of hot espionage plots during the Cold War.

Sunday, June 25 - After a leisurely breakfast, we will untie from the raft-up and head out for some sailing and make our way across the bay to Annapolis. The plan is to arrive in Port Annapolis at approximately 3 p.m. which will allow for some relaxation time, a swim in the marina pool, and/or shower before heading out to a restaurant in the harbor areas of Annapolis. Dinner that night will be sorted by interest, restaurant, or preferred walking distance. It's up to you. Below is a map of the marina. We have slips reserved and that cost is included in the trip price.

Durding Ice Cream Monday, June 26th - After a busy night out in Annapolis, we're planning a leisurely start to the day and hoping the weather cooperates. We will make our way back out to the Bay and anticipate having some good sailing before returning to Haven Harbor. Everyone helps to clean out the boat, gather bags and load cars and don't forget hugs goodbye before the drive home. Make time to stop at Durding's ice cream parlor in Rock Hall for a sweet goodbye.


The Boats:
EOS - 37' Beneteau
  2-Double Staterooms   -   Double Salon
  Bow Thruster    Roller furling Genoa and Main
  Beam - 12' 10"       Draft - 4' 8"
Pegasus - 36' Catalina
  2-Double Staterooms   -   Single & double Salon
  AC      Roller furling Genoa
  Full batten main/Dutchman
  Beam - 11' 11"       Draft - 4' 5"

The cost of this trip is $350.00 per person (Skippers & Trip Leader - $186.00 ). The price includes charter fees and slip fees for the night in Port Annapolis. Provisioning, fuel and 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 8, 2017 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 $250.00 will be due May 10, 2017. 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, NJ 08889



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Current Trips

Schedule of our trips

OWT Trip

Rock Hall. MD
May 20-21

July Trip

Day Sail
Barnegat Bay
July 9

Sept. Trip

Baltimore Inner Harbor
Sept. 15-18

October Trip

Tilghman Island
Oct. 20-23

Jan/Feb 2018

Winter Get-Away
Jan 27-Feb 6 2018