When you are looking for a trailerable, obviously you will be looking at
a substantially smaller boat than you have perhaps been used to with
your marina kept boat. If you are willing to compromise in certain
aspects, you should be able to find something you like and that fits
your budget. As a suggestion, go to www.boattraderonline.com and enter
"trailer" into the "keyword" when doing a search; lots of interesting
boats come up. If you are on a strict budget, I suggest looking at
something well below your price because as we all know, it will cost
more to get it "just the way you want it" and ready to go cruising...
Try looking at outboard powered, retractable keel boats around 26' or
less. At less than $10,000, an older Balboa 26 or Chrysler 26 are not
bad boats and are certainly trailerable with any full size pickup or
van. An O'day 240, Beneteau First 235 or something similar might also
work for you and can be obtained on a budget. Remember though, that
once you get the boat to the water, you have to step the mast and some
boats aren't as easily rigged as others. You may want to look at one of
the MacGregor 26's also. I personally don't care for them, but their
ease in trailering, mast stepping and amount of interior room for their
size cannot be overlooked. What you are describing as your search
criteria is exactly what MacGregor had in mind when he built these and
he sells a ton of them...
Another consideration is racing. If you have any experience and/or
desire, racing is a blast and there are several yacht clubs and sailing
centers that will allow racing boats to be kept as "dry-sailed" boats,
on your trailer and fully rigged; I know several couples that race their
boats and then stay the weekend on them. There are lots of
possibilities open to you... -DK