Back in 2003 I made that trip with my wife and 2 daughters. West coast of FL (Naples) to east coast of Puerto Rico, and then later thru all the USVI.
My thoughts/opinions, admittedly based only on one trip, one way:
- We went in June/July. Yes, that’s in Hurricane season, but it’s the early months and we didn’t have any storms going on the entire trip.
- I had 400 gal of fuel plus 10 five gallon jugs and a 55 gallon drum. I didn’t need the extra until the overnight leg (see below).
- We went thru the Keys, the northern Bahamas, the southern Bahamas, Exumas, to Providenciales (Turks and Caicos), Grand Turk, Samana (Dominican Republic), Isla Desecheo, Mayaguez PR, and finally Roosevelt Roads NAS (Fajardo, east coast of PR).
- It took 2 weeks. We stopped every night except for the leg between Grand Turk and Samana.
- There was a high located over the central Atlantic that made it a clear but high wind/wave trip. The wind was 20-30 out of the east the entire time. We stayed in the lee (west) of the Bahama chain and the Exumas when able, but the southern Bahamas get real shallow so we were forced out in the open for a lot of the trip. Most of the way we saw 6-8’ seas. Once we got south of the Bahamas and into the Turks and Caicos we were regularly going against 10-12’. Green water over the bow was a new and unpleasant experience for us.
- We lived in Puerto Rico for almost 5 years. My view is that the months from Nov to June are windy and always out of the east.
- The months of July - Sept are increasingly flat and beautiful for cruising. Except that the chances of hurricanes also increase in frequency with each week during those same months.
- When there is no threat of a hurricane for your path the late summer/ early fall months are the smoothest. But you’re going to need speed to run if needed, and very good and frequent weather reporting. Otherwise the shoulder seasons (June/July and Oct-Nov) might be 2nd best.
- Again, I did this once. There are probably people on here who’ve got way more experience making this crossing. I would look for their input.
If you want to talk more about it feel free to PM me and I’ll give you my phone number. I will say it was, at that point in our lives, the trip of a lifetime - it was amazing, life-changing. It’s the experience that sold us on cruising for the rest of our lives. But it had some difficult, and sometimes frightening points as well. But it was worth it.
Good luck!