Sailing
Sail Program
On the water April through October. PSC bareboat charters sailboats for all our trips; we do not use member's boats. For those new to PSC, you will want to be a member because PSC membership is required for all trips. For more information, Contact Us or, better yet, come to the next meeting where our sign-up Reservationists can answer many of your questions.

Lots of opportunities for exploring and learning. We start with the usual Spring Skills weekend in late April and finish the season in late October. In additon to quite a few weekend trips on the upper Chesapeake Bay this program usually offers one or more week trips on the waters of the Bay or the northeastern US.
Over the years the Sail Program has scheduled week long trips at these locations:
Maine
Nantucket
Block Island
Cape Hatteras
Lake Huron North Channel
Delmarva circumnavigations
Middle & lower Chesapeake Bay
Lake Champlain
Lake Michigan
Narragansett Bay
Long Island Sound
Martha's Vinyard
Lake Superior Apostle Islands
The sailing schedule is announced shortly before the January meeting and sign-ups begin immediately. Checks only. Below are this year's Sail Program sailing trips.
Extended (exotic) Trips (many in foreign waters): explained and past trips are archived here.
Most recent Trip: -- March 2023 Saint Martin Details
2024 Sail Program
PROGRAM DETAILS: whom to contact, boat cancellation deadlines, and printable pages.
NOTE: boat cancellations are 45 to 90 days before sail date
Spring Skills - May 11 & 12, 2 days
$575
(Boarding 5/10)
This trip is great for sailors of all levels and a great introduction to sailing. We are offering 1 skills trip this year so don't miss your chance to learn or improve your sailing skills. Your ECM will be asking you which skills you would like to work on. Do not miss the chance for a weekend of sailing custom-tailored to your needs.
Memorial Day - May 25-27, 3 days
$625
(Boarding 5/24)
Come explore Chesapeake Bay this holiday weekend with PSC. Even on one of the busiest weekends of the year, PSC is able to find quiet creeks to spend the night in. With luck, along with great sailing, we will enjoy post sail swims as well, or maybe a marina where we can enjoy local ambiance and restaurants (but remember marina fees are not included in the price)
Chesapeake Mid-Week - June 3 - 7, 5 days
$675
(Boarding 6/3)
Five days of sailing the waters of the Chesapeake Bay in the early summer! Join the club as we extend our reach to potential destinations like Annapolis and St. Michaels
Pacific Northwest - July 13 - 19, 7 days
$1,330
(Boarding 7/12), Bellingham, WA
The San Juan Islands, located in the northwest corner of Washington State, are a cruising paradise. These islands boast sheltered waters, magnificent marine parks, quiet villages, and welcoming marinas. Wildlife abounds on the land and in the sea, where deer, bald eagles, sea otters, seals, sea lions and orca whales are commonplace. Food, beverage, mooring and docking charges are not included in the cost of the trip. Note: two weekend trips prerequisite for this sail.
Labor Day - August 3- September 2, 3 days
$630
(Boarding 8/30)
With three days to sail, there are so many places we can get to on this trip. This is your chance to explore the bay be-yond the environs of Rock Hall. This is a great time of year to sail; it is still warm, but there is wind as well.
Ride the Wind - September 21 & 22, 2 days
$565
(Boarding 9/20)
Fall typically has the best wind of any season on the bay which is why this is a club favorite. We've had just about perfect sailing and weather conditions in previous years. We'll go wherever we will have the best sai
Destination Sail - October 5 & 6, 2 days
$560
(Boarding 10/4)
Celebrate the end of our season with a trip to Baltimore. This year we hope to sail across the bay and spend the night in Baltimore. We will celebrate the end of our season with happy hour on Saturday evening. If you are still hungry, dozens of restaurants will be just a short walk from the marina or enjoy a walk around this picturesque area of the harbor
Trips are out Haven Charters in Rock Hall unless otherwise noted. All Haven trips board on Friday evenings .
More Fine Print: You must be a PSC member to sign up for PSC trips. To sign up for a week or longer trip, you must have sailed on at least two weekend trips on PSC chartered boats. Day sails do not qualify as weekend trips, even if two are taken. Un- less otherwise noted, payment in full is due at signup, and expenses for preboarding, food, pump out, fuel, docking, or moorings, if any, are not included in the published prices. These expenses are shared by all crew including ECMs, and typically reconciled at the end of the trip. Cancellation fees are $40 for weekends and $75 for weeklong trips, if replaced.
Trips will not be canceled nor refunds made unless cancellation and refund is made by vendor