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Visiting the 2025 Annapolis Sailboat Show, Schooner Woodwind & Sneak Preview of the Haulout

December 5, 2025 · 8 min · 7K views · Annapolis, Maryland

Schooner Woodwind sails under full canvas on Chesapeake Bay

What this video covers

James and Victoria attend the 2025 Annapolis Sailboat Show, arriving after the first day and joining a Latitudes and Attitudes party the opening night.0:24 The social intensity after extended solo sailing is noted. The standout experience is a private sail on the Schooner Woodwind — now owned and operated by 59 Degrees North — on the Chesapeake Bay, with patrons and subscribers aboard; the schooner is recognizable as the boat featured in the film Wedding Crashers.2:11 Andy Schell of 59 North describes the Annapolis show as his favorite week of the year.6:56 Victoria, a guest, grew up sailing these waters and introduces James to blue crab.7:12 The segment closes with a preview of an upcoming mini-series: a mid-circumnavigation refit in Langkawi, Malaysia, where Triteia will undergo major boat projects in preparation for an Indian Ocean crossing in 2026, with Sam Holmes appearing as a guest.7:37 The channel Sailing Soleil is mentioned for additional Annapolis show coverage.7:19

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Boats in this video

Alberg 30Their boat

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