Sounds like you want a trailerable boat with decent living accomodations, and with a fair amount of seaworthiness as well (needed for San Juans etc).
I'd ask: what's your budget
? And don't forget to consider operating and towing costs.
were generous, from what you've said so far I'd think a Ranger
27 or 25 would be pretty near perfect.
For quite a bit less, maybe a used Sea Sport 27 Navigator or Pilot. Sea Sport also made a nice 24 XL.
power, C-Dory boats are great - really well designed for cruising, very simple, economical, and seaworthy
, ranging from 22 to 26 feet.
option is a Rosborough RF246.
We started with a C-Dory 22 Cruiser, and after Lake Powell and several other big lakes graduated to the San Juans and BC's Gulf Islands, further north in BC, then on to a summer in Southeast Alaska
in ours. We've since moved to a much heavier 26-foot diesel
powered cruiser, with more comfort and amenities than the 22 C-Dory.
There are so many tradeoffs. For instance, one key one is how much weight are you willing to tow, and thus how big a truck do you need. Of all the above boats, maybe only the C-Dory 22 and 23 are safely towable around the west with a Grand Cherokee.
To make a good choice, you'd need to think through several aspects of how and where you might use your boat. Kinda hard to do without cruising or at least boating
experience. Or, you could start small and simple as we did, learn some, and maybe switch to a bigger more complex boat later.
To consider some of the tradeoffs in boats, boat design, and equipment
, you might find it interesting to check out my book on small power boat
cruising of the Inside Passage
, "Cruising in a Big Way". It's available with a sizable preview to look at on Lulu.com. Also on Amazon.