Having a boat that you can keep on a trailer will save you thousands of dollars in marina and storage expenses. It will also severely limit your choice of potential boats.
Without knowing what body of water or where you intend to use your boat also makes it difficult to suggest a particular model.
You can have a trailer made for nearly any boat but launching a fin or full keeled boat at most launching ramps will likely be difficult if not impossible.
That said, you might start out by looking at the MacGregor line of boats. The MacGregor models <= 25' are routinely trailered but are a bit older. Of the 26' MacGregor boats I would only suggest looking at the 'S' model (not the 'X', 'M' or 'D' models) as it is a better sailboat then the others, has room to sleep 6 but is not really suited for heavy conditions you might find out on an ocean. Hunter makes a 26' that is also a water ballasted boat.
Where you intend to use it is an important part of the calculus.
"The cure for anything is salt water~ sweat, tears, or the sea." ~Isak Denesen
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