I think the best way to cruise the Caribbean with only 30 days available would be with a Macgregor 26 with a 50hp outboard on the back. Sorry, I couldn't resist. Just kidding.
Seriously though, the Norsea 27 would be mt first choice for a trailerable offshore cruiser. Many have crossed oceans and Lyle Hess was a great designer (the Pardey's 2 boats were designed by Hess) The Falmouth cutter 22 would also be a good choice. Both are solid offshore capable boats that happen to be trailerable.
Tager - how's the new boat?