I sailed back and fourth in the Caribbean
for a year now, including your stretch three times (one time single
handed) in the smaller sister to the Salina, the Orana
. If you have decent experience from your Hunter
39, you'll do very fine.
My advice to you would me to sail, not motor, even if its upwind. More comfortable and in my view faster. Don't point too high, make sure you do at least 7 knots, and the ride will be alright. The boat will probably slam from time to time, but they are built to take that punishment.
Check passageweather before you leave so you don't have the reef in unprotected waters. Too little sail is also not good as it doesn't give enough drive into the waves.