2026 Season Kick-Off Cruise
May 2–3, 2026 | Possum Point Bay, Mill Creek, Whitehall Bay, Annapolis
38* 59.56' N, 76* 27.14' W
Every season deserves a proper opening act—and this one keeps it classic.
Join us for the 2026 Season Kick-Off Cruise, a relaxed early-May overnight to Possum Point Bay, one of Annapolis' best anchorages and a longtime favorite for good reason.
We’ll anchor and raft up tucked in behind Possum Point on the west side of Whitehall Bay. The holding is solid, the protection is excellent, and the vibe is exactly what a season opener should be—easy, social, and unhurried.
Why this spot works:
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Well-protected anchorage with dependable holding
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Ideal for rafting up and reconnecting after winter
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Plenty to explore on the nature trails in Greenbury Point Conservation Area under the shadows of the three NSS Radio Towers.
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Simple plans, good company, and boats finally back where they belong
No slips. No schedules. No pressure. Just a fun start to the season, a quiet anchorage, and the familiar sound of cockpit stories reminding us that sailing season is officially upon us.
Mark your calendar.
The 2026 season starts here—right where it should.