She is small, but she is mighty. I have to keep telling myself that. It can be easy to forget when you’re alone, 400 miles offshore, and green water is pouring over the deck with every swell. My singlehanded trip from Fiji to Australia aboard the 26ft Contessa, Crazy Love, wasn’t planned that way. In fact, none of my trip has really been planned in the normal sense of the word. But there it is.

I’d left Los Angeles aboard a 31ft Hunter with plans to cruise around Mexico a few months. Now it’s over two years later, and I’m sailing a different boat on a different continent. Only the vastness of the Pacific has remained constant. I ended up selling the Hunter after arriving in Tonga and realizing my cruising friends were probably right—boats like my Hunter just weren’t built to stand up to the rigors of prolonged bluewater passagemaking. Fortunately, I’d met some fellow cruisers back in Pago Pago, American Samoa, the previous year who’d just arrived from Fanning Island on the boat that would soon become my own.

In Pago Pago, the previous owners had been well-known throughout the anchorage after they’d had to be treated for infected bedsores at the local hospital upon their arrival. Apparently, Crazy Love had been so wet during the two-week passage they were never able to fully dry themselves. I remember using them as an example when people told me I was bonkers for sailing my Hunter across the Pacific. At least I wasn’t bonkers enough to go to sea in that!

It wasn’t until I went home for cyclone season that I began to reflect on my trip thus far and think about the upcoming sailing season. Though I’d felt I had done everything I could to prepare the Hunter for bluewater cruising, she still creaked and groaned in ways that would give me pause. Even worse were the times I’d see the hull itself flex as the boat passed over an especially large swell.

A few weeks after returning to Tonga, I got a call from Crazy Love’s owners asking if I had any interest in buying her. Apparently, they’d decided to put her on the market to pursue other adventures. After hearing about their passage to Pago Pago, I couldn’t blame them.

My initial response was to dismiss their offer out of hand. I was eager to get my own boat back in the water. The Hunter was also undoubtedly the more comfortable of the two. Not only was it much larger, it had all kinds of doodads! A watermaker, an SSB radio, digital tank monitors, radar, autopilot, a water heater, refrigeration—you name it, I’d installed it before leaving Los Angeles. Crazy Love didn’t even have standing headroom.

After another few weeks of sailing around Tonga, though, I began to see things differently. I couldn’t stay in Tonga forever, which meant I’d soon be making another bluewater passage. Then there was the afternoon I’d spent sitting over that fancy watermaker, diagnosing a leaky lip seal. I hadn’t particularly wanted to be on the boat at that moment—there was an epic little surf break in the next bay over. But I couldn’t have gotten to it anyway, because the outboard on my dinghy had also stopped working. It may sound a tad dramatic, but I felt like I’d become a slave to my boat. The whole idea had been to use the boat to experience a sense of ultimate freedom, and yet here I was doing chores. Something was backward.

I thought some more about Crazy Love. Her dinghy certainly didn’t have an outboard. The crew just rowed everywhere, which meant there was also nothing to malfunction. A watermaker? Ha! The boat’s house battery (yes, “battery,” singular) could hardly power the running lights, let alone run anything mechanical. Instead of spending their time “fixing things in exotic locations,” her crew simply enjoyed the locations they sailed so hard to get to.

Then there was Crazy Love herself. After doing a little research on the Contessa 26, I discovered the boat has a pretty impressive pedigree, to say the least. The design was modeled after the renowned Swedish Folkboat and made famous by Tania Aebi’s and Brian Caldwell’s solo circumnavigations. In other words, though small, Crazy Love had some serious credibility as a bluewater cruiser. Next thing I knew, the romance of the idea of voyaging aboard such a boat had completely eclipsed any thoughts of the previous owners’ bed sores.

So, I called back the owners of Crazy Love, we made a deal and the next thing I knew I was packing my belongings into a couple of duffel bags and hitching a ride on a friend’s boat to Fiji, where my new home was waiting. After that I spent two weeks in a boatyard taking care of some routine maintenance and adding some new through-hulls, resealing the deck hardware to ensure a dry ride and adding a few safety systems (notably, AIS). After that, I was off to the races—figuratively, speaking of course—for Crazy Love wins no races.

My first experience of what Crazy Love was like underway came as I was motoring away from the boatyard. Crazy Love is fitted with an 8hp, single-cylinder, saltwater-cooled Yanmar diesel. Even at 26ft and displacing 5,400lb, she is severely underpowered, and I found myself struggling to make even 2 knots against a headwind. Looking back on that admittedly frustrating time now, though, I realize my mistake. I still had my old Hunter mentality, a mindset in which, faced with headwinds, I would just turn on the engine. Nowadays, I am far more inclined to just keep sailing In fact, I find myself using the engine less and less. Instead, I listen to what the wind is telling me. Crazy Love is a sailboat. The engine is purely auxiliary. Plenty of Contessa owners have ditched their diesels altogether in favor of a lightweight transom-mounted outboard. I am thinking of doing the same.

I suppose that’s the first and most significant benefit of moving over to Crazy Love. I’ve transitioned from a cruiser-who-sails back to a sailor-who-cruises. Aboard the Hunter, whenever I visited a new island group, I’d try to visit as many anchorages as possible, often motoring in unfavorable conditions just to see someplace new. Nowadays, I tend to stay in one place, and if I do move, I only move when the winds are favorable. Sailing has become what it used to be for me—an activity done for its own sake, instead of a means of simply getting to a destination.

Another benefit of staying in one place longer is that my interactions with the locals there become more meaningful. I also spend less time stressing about what’s next. Instead of wasting my time fixing fancy doodads, I spend my time doing what I came out here to do—which is whatever I want!

Then there’s the money. As a practical matter, having a simpler boat dramatically reduces cruising costs. One of the big debates I had, when I bought Crazy Love, was whether to install a refrigerator—a silly idea in hindsight. Estimating the cost of installing a refrigerator and then dividing by $2.75 (the cost of a cold beer in Fiji) quickly revealed I’d have to buy a lot of cold beer before the fridge would earn its keep—never mind the stress of maintaining the equipment or having the power to run it.

Finally, let’s face it, on a small boat, your sailing skills improve tremendously. I no longer feel like I’m at any kind of disadvantage compared to where I could go aboard my Hunter since I can now sail about anywhere on Crazy Love I would have otherwise motored. Instead of worrying about the next oil change, I get to enjoy my time sailing. Crazy Love isn’t burdened with all the gear that I had aboard the Hunter. As a result, she is fast and nimble—for her size, that is.

How fun is Crazy Love, to sail? Consider this—in New Caledonia, I was traveling as part of a small group of boats I’d met in the Loyalty Islands, and when we got to Prony Bay, the first thing everyone wanted to do was to go daysailing with me. In the end, no less than five of us spent a phenomenal day just tacking back and forth for the heck of. (I would have loved to take more, but six passengers put my cockpit drains below the waterline.) They all said it was the most fun sailing they’d had in years—and these are full-time cruisers!

Granted, later on, as I was making my 4.5 knots toward Australia, there were those days when I wished I could have been aboard something more substantial. There’s also no denying the motion on a smaller boat is more extreme, as are my emotions. And yes, there are days I get pretty wet. (Not for nothing have Contessas been described as “submarines with sails.”)

On the other hand, aboard a smaller boat, like the Contessa 26, any issues I might encounter are both easier to identify and easier to fix. The loads on Crazy Love’s rig are also exponentially lower and the mechanical complexity of the on-board systems much simpler than you’d find aboard a larger yacht. In answer to the question of whether I feel less safe aboard Crazy Love than I would on a bigger vessel, truthfully, I can’t say. Sure, sometimes things seem scarier. I am only a foot and a half above the water, after all. But then again I have to remind myself that I’m on a boat that’s been expressly built for just this type of adventure. She’ll make it.

In the end, I think the real question is whether I’m happier now after ditching the complexity of my previous boat. With this in mind, I look back on how much I’ve already changed since my last season on the Hunter. I remember cursing under my breath while making 2 knots upwind to the next anchorage. Why did I put myself through that? It’s not that I couldn’t have adopted a different philosophy aboard the boat I had. I was just so busy trying to keep up with everybody else that I didn’t allow myself to slow down. I needed to be taught that lesson. Crazy Love forced me to learn. I no longer worry about what newly installed gizmo might fail next. I no longer rush to the next destination. Sure, when sailing with others, I may leave port first and get to the anchorage last. But I promise you when I do arrive, my smile and my sense of accomplishment are the biggest in the whole fleet. 

May 2020