The title of this blog really could be “why don’t you buy a bigger boat?” We’ve been sailing Calypso, our 28’ Bristol Channel Cutter, since we bought her in 1992 (okay, fine, we spent a few months actually getting her ready to go in the water . . .). She’s carried us, when it was just Jeremy and me and our beagle, Toby, from Texas to Florida, down the Eastern Caribbean all the way to Trinidad and west to Bonaire. Back up the East coast of the US to Virginia. She’s carried us, as a family of 4, from Virginia to the Bahamas and Dominican Republic and back again. And we’re getting her ready to take us, just the two of us, no kids or dog, on the next adventure, though where that adventure will be remains up in the air.

Yes, she’s cozy. The current set up down below has the head under our bunk. This was fine when we were in our 20s, but now, ahem, the bladder doesn’t last all night. There’s no way to take a shower down below. I don’t mind jumping over the side for the bulk of my bathing, but these days I’d like to make sure I can get clean even if it’s not the best weather outside or we’re on passage for longer than 4 days. Jeremy, who’s 6’2” tall, can stand up only under the hatches.

So why not buy a bigger boat? One that has, say, a dedicated space for a head and shower down below, with an actual door that closes? One that has, say, standing head room all through for my vertically-endowed husband? Why not spend the money, save the effort of an interior refit, and get something more comfortable?

Believe me, we’ve discussed this one to pieces. We’ve chased boats on Yachtworld, flirted with the idea of weekend trips to see some, and even exchanged emails with a builder. I send Jeremy links to interesting looking boats when they flit like fairies across my screen.

There aren’t a lot of boats that fit our criteria. Boats that look gorgeous (and unique) in our eyes as we dinghy away from them in an anchorage. Boats that sail well. Boats that can carry sufficient supplies for the passagemaking we plan to do. Boats that are simple, robust. Boats that offer substantially more of most of these items than we’ve already got with Calypso, which means we’re looking likely at boats in the 40’ range. Boats that won’t require a mortgage.

Here’s what it comes down to, for us. Comfort is in more than space. Comfort is in knowing the boat. I know where to store things, how to access them. Jeremy installed the engine, installed the watermaker, ran the wiring. I can hoist the main by hand, no need for a winch until that last bit of tightening. We’ve got our anchoring hand signals down, know the routine about how to tack, and can put a full coat of topsides paint on in an hour.

Comfort is in knowing the issues we face. Any boat that would fit our budget, the budget we’ve settled on that will enable us to sail for a long time, will have to be one that’s older. One that requires a lot of work, likely. We know the work Calypso needs. Any new-to-us-boat would come with challenges known and unknown – we might spend a lot of time and money on a different boat and realize that she doesn’t work for other reasons. 

We’ve had enough experience with cruising on Calypso to feel reasonably sure of our projected budget, though of course healthcare and health insurance is the hugest unknown factor out there. We are also practical enough to know that at some point, we’ll be no longer able to live on the boat. We want to have a cushion for that eventuality.

This isn’t to say we won’t get out cruising and decide we need a larger boat. We’re keeping that possibility in mind. But maybe, with the changes we’re making to the interior of the boat, we’ll find that cruising in her is as possible now as it’s been since 1992.

When we first bought Calypso, we were (and remain) heavily influenced by Lin and Larry Pardey, whose philosophy is “Go small, go simple, and go now.” Other boats on our short list included boats like the Beneteau 30. A Jeanneau 32. A NorSea 27. Even an F-27 trimaran. They were boats we could afford, not only to buy but to maintain and cruise on. The choice we made has stood the test of time.

I know that a lot of people reading this are thinking we’re nuts. I’m not sure, if I were making the decision as a boatless person right now, I’d choose something quite as cozy as Calypso. But there is deep value in changing the question from “how big a boat should I buy” to “how small a boat can I make work for me?”

Your boat may have a separate head and shower. But when we share an anchorage, we’ll still see the same sunset.

See you out there.