Caribbean route
Good morning Liam,
Lady friend doesn't want to go as early as November, so we'll be following you.
80nm over water!!?? Ha! The Caribbean route that I use and recommend has over 500NM over water.
You didn't say if you were already familiar with the Caribbean portion of the trip, but here's my recommendations for part of it.
Ft. Pierce - Grand Turk. You can also land at Providenciales, but GT puts you a little farther along for the next day. Check to make sure GT has avgas before going there. Provo always has gas.
GT - Nevis. Long stretch, but after a while you have plenty of detour options if problems arise. We used to have a house on Nevis, and in spite of the 4 Seasons hotel its still a very special place. I recommend staying at the Golden Rock hotel if you can get in.
If Nevis doesn't appeal, you can always go to St. Maarten or St. Kitts for good service and overnight.
Whatever you do, avoid Puerto Rico. Not a bad place to visit, but why would you? Plus, the worst customs agents I have ever encountered. It breaks up the trip from Grand Turk onward, but will add far more time on the ground than it saves in the air.
Cheers,
Don