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The Sailing Club, Inc.


October is a fantastic time of year to sail the Chesapeake. This trip takes advantage of the best the Bay has to offer all packed into three fantastic days!

On Friday, October 16th, we will make our way to Haven Charters in Rock Hall, Maryland. Two sleek and graceful sailboats will be awaiting us. Once boats are checked out and your skipper has given the okay, crews may load personal items and provisions on board. We will meet at a Rock Hall restaurant for dinner about 6:00 p.m. and get to know each other.

We’ll head out into the Bay on Saturday to a destination that is determined by the prevailing winds. We have many choices in that area that are still a short distance from Baltimore’s Inner Harbor. We’ll raft up and spend the evening grazing on the sumptuous offerings that are typical for a Club appetizer party.

Ft. McHenry Bertha's Mussels

Sunday’s journey will take us up the Patapsco River. Up we go … past Seven Foot Knoll, up past White Rocks, and eventually past Fort McHenry, Even if you’ve been to Baltimore lately, it is always a special feeling to sail into a harbor so intimately connected with America’s history. We have slips reserved at the Inner Harbor East Marina, which is a short walk to Inner Harbor attractions such as Little Italy, and Fells Point. While you can always enjoy a superb dinner at Bertha’s Mussels, there is a wide choice for dinner and activities. No doubt most of you will take your fill of indigenous seafood delicacies on Sunday night. Regardless of what other delights and temptations you choose to indulge in while in Baltimore, this evening belongs entirely to you!

Monday’s start back to Rock Hall can be a leisurely departure, as it is a short, 10 nm or so, sail. Perhaps a quick visit to the National Aquarium or the Chesapeake Lightship. Or, as the winds this time of year are usually brisk, perhaps the call of the sea beckons you to get one more full day’s sail in.

The cost of this trip is $400.00 per person (Skippers and Trip Leader $210.00). The price includes charter fees and one night’s slip fee at the Inner Harbor East Marina. Provisioning, fuel, pump-out, and other incidentals are additional and will be handled by each boat’s crew. A $100 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 Henry Gibson at the address below. Reservations will be processed beginning April 4, 2020 with a random draw of those reservations received by that date. All reservations received after that date are on a first-come, first-served basis. The balance of $300.00 will be due September 2, 2020. The Club’s standard 30 day cancellation policy applies.

A pre-trip meeting will be held about 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 coordinate travel plans.

Trip Leader

Assistant Trip Leader

Steve Krakauer

11 Clark Ct

Basking Ridge, NJ 07920


Henry Gibson

19 Filmore Ave

Livingston, NJ  07039


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




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Current Trips

Schedule of our trips

Chesapeake I

Rock Hall, Chester River
Annapolis, MD
June 5-7, 2020

Chesapeake II

Rock Hall, Eastern Bay
Herrington Harbor, MD
June 8-11, 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

Winter Getaway

Tentatively for
Jan 30 - Feb 8, 2021