I bought a sailboat… yes this sounds like a sequel to the sailing kayak trip.

I bought a sailboat even though all the sailing stories I’ve ever read had fear, loneliness and hardship has main themes, and the only sailor’s proverb I can remember goes: “He that would go to sea for pleasure, would go to hell for a pastime”.

My own experience on a sailing kayak had not included a lot of comfortable moments or security, yet when I got home I knew that sailing from Miami to Montreal remained the most meaningful experience of my life.

The trip brought me closer to what I wanted to be when I grew up, at least a closer approximation of what I thought I should be. Unfortunately, it made me even more quirky and unlikely to adapt to the comfortable suburban lifestyle that seems to be the norm across the continent. I think I’d be happier in a wealthy agricultural commune, with a lot of pretty and favorably minded girls with a soft spot for blue eyed sailors, and a pub.

This new trip is not specifically meant to be an ordeal. “This time will be different” I told my friends. I have no objective apart from relaxing and fishing around the most accessible island paradise I can find. Moreover, I bought a spacious coastal cruiser, a 1985 Newport 27, instead of a pool-side play toy. The Newport is beamy and I can walk in the cabin without touching the ceiling. It’s rigged for solo sailing. I have all the electronics at the helm, self furling jib, a working diesel and autopilot.

I have a few modifications to make before I can take it into moderate seas. I have to install a second automatic bilge pump, repair the hand pump, block two speaker holes, and set a second battery and a solar panel. The boat came with a furling genoas and a main sail with two reefs. I’ll try to get some storm sails so I can cope in a sudden weather change.

I also have a few things to learn. I’m not that worried about open ocean passages as much as port entries, negotiating inlets and boat maintenance. The diesel engine and the electrical systems are quite intimidating. The boat has so many systems that can go wrong, from the toilet to the bilge pumps, and I can only count on myself to fix everything. Top side, I have to deal with the complicated riggings of a cruising sailboat. Everything is in working order but I can see that I should upgrade some lines and learn what they are supposed to do. I also need to learn how to go up that mast so I can access the mast hardware if something goes wrong.

I’ve sailed the boat before heading back to Montreal. I got it in and out of the docks without incident and I sailed the boat for a few hours. The reassuring thing about a cruiser is how slow everything goes in comparison with a sailing dinghy. On a small sailboat, you’ll capsize if you merely look the wrong way. On a cruising sailboat, you can walk upfront and get back to the helm without the boat changing direction, and that’s without the autopilot. The challenge with the cruiser is that everything is under greater pressures. You need winches and complicated pulleys to control anything.