The Sailing Club Logo

The Sailing Club, Inc.

Celebrate the longest days of the year with a long sail from Rock Hall to Crab Alley Bay, and then on to St. Michaels. A perennial favorite, St. Michaels, Maryland, offers interesting sites, great restaurants, and marinas with great services.

This trip balances long sailing days, a quiet anchorage, and time ashore to visit all the sites that make St. Michaels, Maryland, so popular.


Thursday, June 20
Early boarding in Rock Hall after about 4:00 p.m. Dinner ashore.

Friday, June 21 (33 nm)
We'll need an early departure from Rock Hall in order to sail to Crab Alley, located on the south side of Kent Island. As going through Kent Narrows is not allowed by the charter company, the sail will take us south from Rock Hall into the Bay, around Kent Point and up Eastern Bay. Crab Alley is protected from the southwest and north, and provides great anchoring for our raft-up and traditional Club appetizer dinner party.

Saturday, June 22 (10 nm)
Sail south to St. Michaels and find our reserved slips at the St. Michaels Harbour Inn Marina. Visit the Chesapeake Bay Maritime Museum, the brewery, the winery, or just wander the town. Our slips include use of the swimming pool and pool towels, bicycles, and a shuttle services into town (which is also very walkable). Dinner is ashore at any of St. Michaels’ numerous restaurants. Reservations are recommended, and this will be discussed at the pre-trip meeting.

Chesapeake Bay Maritime Museum

Sunday, June 23 (40 nm)
An early departure from St. Michaels will be needed for the long sail home, retracing the route via Eastern Bay and around Bloody Point Light to Rock Hall, where we need to fuel up and pump out, and be off the boats by 5:00 pm.

The Boats
Two boats have been reserved from Haven Charters. Both have three cabins and two heads, and while docked, air conditioning.

Luff Out Loud (Beneteau 41) Stargazer (Hunter 44DS)

The cost of this trip is $575.00 per person (Skippers and Trip Leader: $304.00, Assistant Trip Leader: $440.00). This price includes charter fees and one night's slip fees. Provisioning, fuel, pump-out, and other expenses are additional and will be handled by each boat's crew.

The deposit for this trip is $100.00. Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed two-page Reservation/Release Form, to Mia McCroskey at the address below. Reservations will be processed beginning April 15, 2024 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 $475.00 is due on May 7, 2024. The Club's standard 30-day cancellation policy applies for this trip.

A pre-trip meeting will be held a few weeks before the trip at a time and place to be announced. All crew members should make every effort to attend in order to meet your crewmates, plan your meals, and make travel plans.

Trip Leader

Assistant Trip Leader

Mia McCroskey

19 Manor House Drive, Apt K12

Dobbs Ferry, NY  10522


Joel Mack

5905 Spruce Mill Dr.

Yardley, PA 19067


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



The Sailing Club
home page

Current Trips

Schedule of our trips

On Water Training

Rock Hall, MD
May 18 - 19, 2024

August on the Chesapeake

Rock Hall; Bodkin and Worton Creeks, MD
August 17 - 19, 2024


Rockland, ME
September  15 - 21, 2024


Solomons Island, MD

October 13 - 20, 2024

Winter Getaway

To Be Determined