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Hake Seward 26/30 seem to be reasonably seaworth and trailerable. Then again, a lot of folks trailer J105's legally under the 8.5' width by tilting them on the trailer! They are reasonably light, that a pickup can pull it. Granted you will want an 8lug SW or dually truck!
Reality is, also, what are you towing it with? Are you talking reasonably new, or older? Some of the older IOR 1/4 ton boats, ie Sanjuan 24, Cal T-4, or some not, ie Catalina 25, San juan has some 26-27' boats that are trailer able that could get from FL to the islands south with some weather planing.
Some boats like a melges 32 have drop keels, that allow them to be trailered easy enough too, Certainly capable of off shore work......BUT, rather lacking in interior niceties. There is a whole slew of options in monohulls.
Another option is an older Farrier 27 or equal style trimarans, trailerable at 8.5', but can move along in the low to mid teen range on good days. Way better than the 3-5 knots at best for a mid 20' mono hull! This can increase your range for a given day.
Then comes budget. A Hake will be 20-30K minimum. An older 24' 1/4 ton ior style boat, you could probably find boat and trailer for $5G if you hunt around.....A J105 or melges 32 figure $80-100K, then a custom trailer at $10K...........
She drives me boat,
I drives me dinghy!