The Sailing Doodles Podcastvideo

Regrets, Romance & Refit: Sailing Doodles Unfiltered

May 10, 2025 · 41 min · 137K views

What this video covers

Bobby White plans to sail from the Bahamas to the Chesapeake in early June, potentially cruising through the Abacos to batch content before attending the Annapolis Fall Show. He intends to host short cruises for patrons and channel members during the event. Regarding future cruising, he prefers the Mediterranean for its town-dock culture but notes the short sailing season, ultimately favoring the Caribbean for its year-round weather. He currently uses Podia to host his sailing school, maintenance courses, and exclusive content, citing lower fees compared to Patreon’s percentage-based model. He uses ChatGPT to organize viewer questions and assist with channel production tasks like thumbnail and title creation. Reflecting on past mistakes, he identifies a transmission fire on his current boat as a significant incident, noting that the standby anchor failed during the event because it was improperly secured. He expresses interest in eventually transitioning to a trawler for the Great Loop in five to six years, citing the ease of navigating bridges under power.

Watch on YouTube

More from The Sailing Doodles Podcast

He Climbed Everest, Sailed Around the World & Conquered the Northwest PassageAug 2026RV Life vs Boat Life — Which Is Actually Better?Aug 2026There Are No New Frontiers LeftAug 2026Will Nika Be Coming Back?Aug 2026

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

The Sailing Directory Newsletter

One email with the fleet's best finds — the moments, boats, and stories worth your watch time. Enter your own address to get your own copy.

Report an issue