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Sailing Doodles · video

Perfect Day at Soggy Dollar… + Want to Join My Crew?

December 5, 2025 · 12 min · 109K views · White Bay, Jost Van Dyke

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What this video covers

A day sail from Cane Garden Bay, Tortola, to White Bay on Jost van Dyke covers six miles and ends at the Soggy Dollar Bar.▶ 1:25 Mooring balls at White Bay are scarce; Bobby secures one, noting the anchorage holding is poor for boats that must anchor.▶ 1:43 The afternoon includes painkillers at the Soggy Dollar Bar, then a one-mile motor around to Great Harbour, where the crew picks up a mooring off Foxy's for dinner and dancing.▶ 4:34 Bobby also announces a crew recruitment offer: a couple is invited to sail with him in Thailand from February through June, roughly four months, during which he will teach sailing, filming, and video editing, then launch a spinoff YouTube channel with them as hosts.▶ 7:41 Submissions require an email to crew@sailingdoodles.com with a purpose-made YouTube video audition.▶ 8:44 Separately, Bobby's 1989 CT-56 is offered in a prize giveaway drawing on January 31st, with a 10-ticket purchase yielding 30 free tickets.▶ 10:58 He also previews an upcoming nine-day charter out of Raiatea covering Bora Bora and surrounding islands in French Polynesia.▶ 7:18

Boats in this video

Island SPIRIT 525Their boatTa Chaio Shipbuilding Co. (TAIWAN) Ct-56Their boat

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From Sailing Doodles — see the channel’s boat, crew, and every analyzed video.

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Not navigation advice · © 2026