I’m Sailing Myself Around the British Virgin Islands in December — Here’s How Deep the Rabbit Hole Goes
In four months, I’m boarding a catamaran at Hodge’s Creek Marina with a small crew, no professional captain, and a sailing résumé I had to write to prove I’m not going to sink the boat. This is my first bareboat charter, and I have learned that “planning a sailing trip” is actually code for "building a small logistics company for one week of your life." // cheesy
Here’s what that’s actually looked like.
Step 1: Realize you need a permission slip to drive a $5,500 boat. No license required in the BVI — just a sailing resume and a skippered checkout where someone takes you out for 4 hours first to make sure you won’t embarrass yourself (or worse). // nice start // I’ve spent weeks talking to everyone who’s done this before me — a coworker, three separate breakroom conversations, an uncle who’s done it, hours //the video was 36mins// of Sailing Uma YouTube — just to build a mental model of things I didn’t know I didn’t know: how to hoist a flag //not an important point//, how to tie up to a mooring buoy without drama, what wind and wave conditions are enough to flip a catamaran. That last one felt important to figure out before the trip.
Step 2: Turn a flight booking into a spreadsheet. Flying into EIS (11 minutes from the marina) vs. STT (4-5 hours away, plus ferries and an entry tax) was its own multi-day //exaggerated// analysis. I ran the actual redemption math on airline miles — turns out American miles were paying out around 1.8 cents each on this booking, solidly above the typical 1.3-1.5 cent benchmark, while Avios came in below average. So the flights got bought a full 60-90 days out, in cash //I used points//, on the better mileage program, because apparently that’s a thing you have to calculate now.
Step 3: Build an entire geography. The BVI isn’t one destination, it’s a loop, and I now have a full stop-by-stop itinerary mapped out roughly south-to-north: Norman Island’s floating bar (yes, it’s a literal historic ship called the Willy T), the wreck dive at Salt Island, The Baths' granite grottoes on Virgin Gorda (go early, apparently everyone knows to go early), the flat coral atoll of Anegada for grilled lobster, and Jost Van Dyke's Soggy Dollar Bar — birthplace of the Painkiller //new stuff not in my notes but accurate//, which feels like the kind of detail that should be printed on the boarding pass. I'm even color-coding mooring spots in an app called BoatyBall before the annual fee kicks in, because why plan a vacation when you can build a database instead. //not how this works//
Step 4: The group chat logistics nobody warns you about. Who’s actually coming (recruiting a friend mid-planning), who’s liable if anything at all goes wrong (there has to be one fully liable captain — no pressure), and yes, I am currently trying to get a permit for a beach firepit. A permit. For a fire. On a beach. In the Caribbean.
The plot twist: this isn’t even the whole plan. This trip is Phase 1. It exists specifically to bank the experience and hours needed before a self-chartered week in Croatia in 2028 — which requires actual certifications (ASA 104 and 114, plus a VHF radio license) because Europe does not share the BVI’s “vibes-based” approach to who’s allowed to drive a boat. And after that, there’s a running list of maybe-someday charters: Zanzibar, Greece, Panama, San Diego. The BVI trip is basically the tutorial level.
So no, I don’t fully know what I’m doing yet. But I have a flight-mileage spreadsheet, a snorkeling itinerary sorted by island, a firepit permit application, and a group chat slowly filling up with people who also don’t know what they’re doing. Feels like enough.