2023 ICOYC Cruise of the Chesapeake

Wednesday, September 27, 2023 to Friday, October 6, 2023
Annapolis Yacht Club

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Registration Form >>


Invitation from Timothy Cusack, Commodore at Annapolis Yacht Club

The Annapolis Yacht Club (AYC) cordially invites ICOYC Members to a 9-day cruise on the beautiful Chesapeake Bay.

The Chesapeake Bay is a large, historic, and beautiful estuary (200+ miles long and 30 miles at its widest point) in the Mid-Atlantic region of the United States. The Bay is considered one of the most delightful cruising areas in the country, and in particular, its Eastern Shore, where our cruise will focus, is renowned for its quiet, pastoral scenery and attractive little towns, making it a desirable destination for all boaters. The Chesapeake Bay itself is welcoming with its soft bottoms, limited tide range and little current. The cruise will begin and end in Annapolis.

The cruise will be hosted and organized by the Annapolis Yacht Club, a full-service, year-round, private yacht club that provides its Members high-quality programs which include sailboat racing, sail and power cruising, a vigorous junior sailing program, educational and social events, a fitness center, and first-class dining  facilities. AYC is proud of its new clubhouse, newly rebuilt from the fire that occurred two months after the 2015 ICOYC cruise. There are also two new facilities – the Sailing Center and the Activity Center.

As a special treat, the United States Powerboat Show is scheduled on the closing weekend so you can browse to your heart’s content.

AYC’s Cruise Planning Committee has put together a great week of activities, and they look forward to hosting ICOYC members at the Annapolis Yacht Club and providing you with a fun-filled week on the Bay.


The current itinerary is:

Date Destination Miles Activities Links to Destination
Annapolis 0 Registration
Tour of US Naval Academy Opening reception at AYC Dinner on your own
Dun Cove 22-30* Late registration at AYC 8am – 10am Cruise to Dun Cove Anchorage
Host boats raft up with BYO happy hour Dinner on own boat
Cambridge 18 Cruise to Cambridge Tour Cambridge
Dinner at Cambridge Yacht Club
https://visitdorchester.org/cambridge- md/
Cambridge 0 Lay Day Dinner on own
Stay at marina or cruise to La Trappe Creek anchorage
Oxford 12 Cruise to Oxford
Informal sail race to Oxford Guided Tour of Oxford
Oyster Roast at Tred Avon Yacht Club
St. Michaels 28 to 36* Cruise to St. Michaels
Activities at Chesapeake Bay Maritime Museum
BYO happy hour w/talk by author Dinner on own
St. Michaels 0 Lay day
Tour St. Michaels on your own Guided Tour of Museum Catered dinner
Shady Side 23 Cruise to Shady Side
Activities at Chesapeake Yacht Club Dinner with live music
Annapolis area 8 to 12 Cruise back to Annapolis area
Individual small group anchorages assigned On shore dinner at AYC host homes
Annapolis 2 to 4 Closing reception at AYC Dinner included
Local Chesapeake Bay Entertainment

If you have any questions, please contact Cruise Chair Sue Pitchford at sue.pitchford@gmail.com