I did that solo sailing last summer with only one over nighter.
With 2-4 day hops, it would be tough to skip the D.R., so probably stop in P.R., then Sousua to check into the D.R., then Luperon to check out. You could skip the T&C and check directly into the Bahamas
, realizing the southern Bahamas are limited in terms of re-provisioning or notable airports. (Depending on the boat and wind
, you might be able to from the VIs, directly to the T&Cs in 4 days, skipping P.R. and D.R.)
You could hit Long and from there to Gerogetown for a re-provision and crew change. Hit an Exuma Island or two if desired, the Berries and back to FL.
My stops were:
Sun Bay Bay, Vieques, P.R.
Isle Des Mortes, P.R.
Puerto Real, P.R. (Didn't go far due to engine
?? (name escapes me)
Rio San Juan
Big Sandy, T&C
Sapodilla Bay, T&C
West Plana (short day after checking in)
Attwood Harbour, Acklins
Little Harbour, Long island
NW tip of Long Island
Great Guana, Exuma (skipped Georgetown)
Abacos where I spent some time due to weather
before hopping to Florida