Amazon Packages & Offshore Lessons: Hold Fast Edition

So Brian, you ask, how does one prepare for sailing around the world? Easy. Step one: buy a boat. Step two: drain a year’s salary into Amazon’s pocket like it’s a slot machine in Vegas!

Flashback to this time in 2021, when I bought this “ready-to-go” world cruiser. She already had wind steering, a bow thruster, a 6k generator, a mountain of batteries, and solar panels—you name it. Supposedly, everything I’d ever need.

But thats not close to everything... So, I added… well, everything else. The marina office turned into an Amazon distribution center—packages stacked higher than a Jenga tower in an earthquake. And that was just shipment one. By the end, I’d clicked “buy now” about 500 times. Five. Hundred. Orders. From Amazon alone.

And that’s not even counting Defender, West Marine, Sailrite, eBay, Craigslist,

Think about it: the list ranged from safety and comms gear—Garmin inReach, Iridium Go, life vests, EPIRBs, personal locator beacons—to everyday household basics like pots, pans, plates, silverware, carpets, towels, and shampoo. Then there were the nuts, bolts, tools, spare shackles, random fittings, and all the other bits that keep a boat afloat and a sailor sane.

In short, if it could fit in a cardboard box, it probably passed through that marina office. Anything you’d need in daily life on a boat—to cook, to clean, to navigate, to simply function as a human—you have to stock it. And not just one of each, but backups, extras, and redundancies for everything.

My Prime account probably christened Jeff Bezos' yacht. Realistically, it was probably just enough to pay for one of the cleats on that monster.

In all seriousness, for anyone considering an endeavor like this, finding the right boat is the most important piece of the puzzle. Any boat you buy is going to come with trade-offs—none of them have everything. This is my third boat, but the first one I’d call offshore-ready. What I’ve learned is that the core of the boat matters far more than the extras bolted onto it. The engine, the rudder, the keel, the rigging, the mast, the overall comfort and layout—these are what truly define the boat.

You buy for the hull, the design, and the way it fits your needs:

• Do you want a full keel or a fin keel?

• A skeg-hung rudder or a spade rudder?

• A staysail on an inner forestay?

• Heavy-duty chainplates or through-bolted bulkheads?

• Deep lockers for passagemaking or higher freeboard for dryness?

• A cutter rig or a sloop?

• A keel-stepped mast or a deck-stepped mast?

• A center cockpit or an aft cockpit?

• The comfort of the berths, the storage, the tankage, the layout that matches how you’ll live aboard.

There is more to that list. The point is the fundamentals are what you can’t change easily.

Everything else—watermakers, solar, batteries, wind steering—can be added later. Yes, a generator or a bow thruster are expensive upgrades and might be worth factoring in, but even then, they aren’t the heart of the boat. In retrospect, I’m glad I have the extras now, but I would’ve bought them anyway. What matters most is starting with a solid, seaworthy platform that already meets your core needs. The rest is just accessorizing.

If you’re going to do what I’m doing, get a Hydrovane International Marine. The redundancy alone is worth every penny—having a spare physical rudder and a completely independent way to steer. Never mind the fact that it’s brilliant at holding course in the wind without burning a single watt of power.

Days Sober: 2,090