2022 Cruising Schedule

Printer Friendly Copy: Click
To View Online Calendar: Click
To Subscribe To An Electronic Copy: Click

AprilMayJuneJulyAugustSeptemberOctober November December

DATE
CRUISE
DESTINATION
April    
April 2
Raft Captain Class Edgewater, MD
April 23
 Cruising Kickoff - Invitation Only
DoubleTree Hotel Annapolis, MD
April 30 Flare and Safety & Dockside Training Camp Wabanna & Various Skipper's Boats
May    
May 1 Dockside Training Various Skipper's Boats
May 4
Day Sail Skipper's Choice
May 7-8 Shakedown Cruise Aberdeen Creek, South River
May 14 Day Sail Skipper's Choice
May 15 Day Sail Skipper's Choice
May 18 Day Sail Skipper's Choice
May 21-22 DNR Cruise & Shore Party Duck Lodge Wye Island, Wye River
May 25 Day Sail  Skipper's Choice
May 26 Day Sail Skipper's Choice 
May 27 Day Sail Skipper's Choice 
May 28-30 Memorial Day Cruise Broad Creek, Magothy River
Reed Creek, Chester River
May 28 -
June 5
Extended Cruise 5/28 Broad Creek, Magothy
5/29 Reed Creek, Chester
5/30 Lankford Bay Marina
5/31 Comegys Bight, Chester
6/1 Port of Chestertown Marina
6/2 Port of Chestertown Marina
6/3 Corsica, Chester
6/4 Eagle Cove, Magothy River
June    
June 4-5
Just a Cruise Eagle Cove, Magothy River
June 8
Day Sail Skipper's Choice 
June 11-12
1st Mates & Something Junish Round Bay, Severn River
June 14
Day Sail  Skipper's Choice 
June 18
Dingy Dance Annapolis, MD
June 19
Day Sail  Skipper's Choice 
June 25-26
Anniversary Cruise & Shore Party Lankford Bay Marina, Rock Hall, MD
June 29
Day Sail Skipper's Choice
July    
July 2-4
4th of July Cruise 7/2 St. Michaels 7/3 TBD
July 9-10
Wine & Chocolate Hollendursky Cove, Wye East River
July 12
Day Sail Skipper's Choice 
July 16
Day Sail Skipper's Choice 
July 17
Day Sail Skipper's Choice 
July 23-24
Christmas in July Rhode River
July 27
Day Sail Skipper's Choice
July 30-31
Appetizer & Dessert Dun Cove, Harris Creek Choptank River
August    
August 6
Day Sail  Skipper's Choice 
August 7
Day Sail  Skipper's Choice 
August 10
Day Sail  Skipper's Choice 
August 13
Town Hall Meeting Chesapeake Yacht Club, West River
August 16
Day Sail Skipper's Choice 
August 20-21
Seafood Feast Cruise & Shore Party Haven Harbor South, Rock Hall
August 23
Day Sail  Skipper's Choice 
August 27
Day Sail Skipper's Choice
August 28
Day Sail Skipper's Choice 
September    
September 2-5
Labor Day 4-Day Cruise 9/2 Baby Owl, Broad, Choptank
9/3 Zahniser’s, Solomon’s Island
9/4 Dun Cove, Harris Creek, Choptank River
September 9-11

Eastport Oyster Boys Cruise
Concert 9/10

Shaw Bay, Wye River
September 10-17
 Sicily Bareboat Trip Aeolian Islands, Italy
September 14
Day Sail Skipper's Choice 
September 17
Day Sail  Skipper's Choice 
September 17
Hospice Cup Charity Sailing Regatta
September 18
Day Sail Skipper's Choice 
September 20
Day Sail Skipper's Choice 
September 24-25
Oktoberfest Cruise & Happy Hour Anchorage Marina, Fells Point Balt. Patapsco River
September 28
Day Sail Skipper's Choice 
October    
October 1
Day Sail Skipper's Choice 
October 2
Day Sail  Skipper's Choice 
October 8-9
Chili Cook Off Cruise Whitehall Creek
October 13
Day Sail Skipper's Choice 
October 15-16
Goose Cruise Corsica River 
October 22
Day Sail  Skipper's Choice 
October 23
Day Sail Skipper's Choice 
October 29-30 Oysterfest Cruise CBMM, St. Michaels
November    
November 5 Day Sail Skipper's Choice 
November 6 Day Sail Skipper's Choice 
November 12 Cruising Wrap Up Invitation Only TBD
December    
December 10  Parade of Lights Ego Alley Annapolis, MD