I think there is a difference between trailer-sailors and trailerable cruising boats.
Trailer-sailors are generally designed to be light, easy and quick to launch, but usually are not as robust. It's easy to take them out for day or weekend, but generally they are designed for lake and easy coastal cruising. I think examples may include the water ballast boats such as the MacGregor
and Corsair trimarans (not water ballast). Most of these have swing keels and other features making them quick to launch at most ramps.
At the other extreme there are boats that were really built for open water sailing which are small enough they can be trailered. Typically these much more solid boats with fixed keels that were not designed to be trailered, but someone built a trailer for. They usually take longer to rig and launch off a trailer and you may be more limited in the ramps that are suitable to launch these boats. (deep enough, long enough, etc.) In addition to the Norsea and Flika mentioned by Tao, I'd add the Contessa 26 also known as the Taylor 26, maybe the Dana, Westerly Pageant, Westerly Centaur, Cape Dory and a number of folkboats.
I owned a Centaur which I sailed across Michigan and Superior in and did several trips of a couple months to the Bahamas in. I purchased it specifically so I could have a boat, I could sail locally, but then tow down to Florida
and use for Bahamas trips. I really liked that it was of the few 26-foot boats with standing head
room. A few have circumnavigated. There are a couple famous stories of Contessa solo circumnavigations and I don't think anyone would question the capabilities of the Pacific Seacraft
boats or Norsea 27 .
My Centaur with a trailer weighed in at about 10,000 lbs, so even with a 3/4 ton truck, towing it was no leisurely Sunday drive. Towing a boat like this is nothing like towing a light weight 17-foot sailboat or 6-canoe trailer.
I've seen people in the Bahamas in boats like MacGregors, but I've seen many of these also feel they were pushing their limits and turn around early. Personally, I would not want to cross with a light weight trailer sailor. Cruising the Keys is something all together different. I've done that in a Catalina 22.
Although, I owned a boat that was trailerable and capable, I largely agree with Paul above. Trailerablity comes with some big limitations and costs. You are limited to a fairly small boat and for the costs of buying
and maintaining a trailer, tow vehicle and price
of towing there may be other options to consider. You could probably charter
a few times for the price
of a trailer and tow. I'm not trying to talk you out of a trailerable boat - just pointing out some of the trade-offs to consider.