Sailing Triteiavideo
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
Boats in this video
More from Sailing Triteia
From Sailing Triteia — see the channel’s boat, crew, and every analyzed video.