It seemed that the obvious thing to do was acquire a small trailer-sailor. After hanging around marinas and spending far too much time on research, there was a clear favorite for me: The Montgomery 15. I bought one of these, and it lived in my driveway until it became obvious that two sailboats were too many and I sold that wonderful boat in early 2004. Learn more about this wonderful little boat here. Although small and light, she's a comfortable and capable boat. The most ambitious trip that I know of in one of these was somebody who sailed one from California to Hawaii. After being out of production for a while, they're being made again by Nor' Sea Yachts, and the Montgomery Sailboats Owners Group website contains a number of interesting links, as well as instructions for joining the Montgomery Mailing List.
I can't say enough good about my M-15, but there was a problem... I was in love with another man's boat.
You see, Friend John has a Pacific Seacraft Orion 27, one of the finest small boats in the world, and I was an occasional guest aboard. Much as I liked Umiaq, some things were a problem. Like size. You can't sit upright in the cabin. Comfortable for me, and more than adequate for me with my pre-teen (at the time) son. But attempting to have the whole family sleep aboard was like sharing a telephone booth with a whale. And there was no denying that the light weight has its negative aspects.
I was told that under no circumstances whatsoever should I even think about buying another boat. But that if I had the incredible stupidity to ignore that advice then it should have full standing headroom and an enclosed toilet compartment. With this heartfelt endorsement ringing in my ears, I told myself that I would just look at a boat or two out of general interest.
There were plenty of boats around. The problem was that there were no PS Orions around at prices within my reach. So I looked at a lot of others that were, well... okay. But nothing that said "I'm The One". I began to wonder if I was hoping for too much. And then one day I saw a classified ad for a boat of a type I'd never heard of: A Vancouver 25. This sounded a bit smaller than I was thinking of, since I was set on something roughly comparable to the Orion, which is 27 feet LOD, and a very large 27 feet. I might not have bothered traveling too far, but the boat was an hour or so North of Philadelphia and I had to go to Philadelphia the next day on business. Not only that, but my family was away, so there was nothing stopping me leaving early.
That afternoon I was walking towards Dolphin, on land at Point Pleasant NJ, and thinking "this is the one". Read more about my Vancouver 25 Dolphin here.