Sailing Into Oblivionvideo

Ep# 27 Interview with Chris

March 9, 2021 · 1h 1m · 78 views · New Orleans

What this video covers

A novice sailor purchases a Catalina 27 at an online auction for $2,500 and attempts to sail it from Baltimore, Maryland, to Florida with no prior experience.2:07 After grounding the vessel in the Chesapeake Bay and losing a dinghy, the crew secures a tow to Annapolis.7:12 The owner eventually completes the transit to Miami by motoring through the Intracoastal Waterway, avoiding bridge openings.19:53 While based in Boot Key Harbor, the sailor supports himself by cleaning boat bottoms using scuba gear and hookah compressors.32:45 He frequently anchors at desolate islands in the Florida Keys, supplementing his diet by spearfishing for lobster and stone crabs.26:14 The account details the logistical challenges of living aboard a small sailboat, including managing ventilation with hatch-mounted fans and navigating the legalities of dinghy access and local fishing regulations in the Florida Keys.59:09

Watch on YouTube

Boats in this video

Westsail 32Their boatCatalina Yachts 27Reviewed

More from Sailing Into Oblivion

Matt Rurtherford Returns to the Show, EP#429 with Atlantic Waves background LoopMay 2026@Sailing With Phoenix | Oliver returns to the show!May 2026Sailing Into Oblivion Podcast EP#422 Offshore Recordings with Background Sailing View LoopMay 2026Sailing Adventures with Brendan and Chanell, EP#421Apr 2026

From Sailing Into Oblivion — 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