Is the Caribbean Becoming Too Dangerous for Cruisers?
October 3, 2025 · 35 min · 52K views
What this video covers
Bobby, host of the Sailing Doodles Podcast, answers roughly 25–30 patron and channel-member questions in a wide-ranging Q&A session covering Caribbean safety, cruising logistics, navigation apps, and his upcoming plans with the Island Spirit catamaran.3:02
On Caribbean safety, Bobby draws a sharp line: the broader Caribbean remains reasonably safe, with dinghy theft the most common nuisance, but he recommends staying at least 200 miles from Venezuela given current U.S. drug interdiction operations and the risk of a U.S.-flagged vessel being used as diplomatic leverage.0:44 He cites a Grenada incident — escaped convicts who seized a cruising couple's boat and killed them — as a rare but real outlier.1:30 On clearing customs, he recommends the website Noonsite for country-by-country port-of-entry procedures and fees, the CBP Roam app for U.S. entry, and the app No Foreign Land for anchorage reviews, mooring costs, and boat tracking.17:37 He evaluates a 1992 Beneteau First 405 listed at $66K as overpriced relative to comparable 2000-vintage boats available for around $100K.27:26 He outlines his planned circumnavigation route starting from Thailand aboard the Island Spirit, heading west across the Indian Ocean, through the Med, across the Atlantic, and finishing in the South Pacific — east-to-west to stay in the trade winds.10:11
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