On the Jeeebus wishlist - which Mrs. Jeeebus has not said no to yet - is the 38' Boston Whaler Outrage:
Boston Whaler 380 Outrage - boats.com
Discover the new 2020 Boston Whaler 380 Outrage - research, view pictures, specifications and dealers near you for this boat or search for more Boston Whaler boats for sale on boats.com.www.boats.com
I wouldn't take it hundreds of miles away to the Virgin Islands, French Caribbean, etc., but we've been looking at buying a place on Bimini (50 miles), Grand Bahama (60ish miles), or Abaco (100 miles) and the crossing is very comfortable on a boat like this. That said, weather and waves are always the key factor even on a 40'+ boat. It could be flat off the coast here and once in the gulfstream you're looking at 10'+ waves. That's not fun on any boat.
those engines are almost 30K each.