I have done the trip south from New England
almost every year since 1996. Here are my thoughts. Enjoy your trip!
1. In the fall, the most safe/comfortable option will likely be to hug the coast, as in 1/2 mile - if you are up for it. I wait for a cold front to come through, and then sail in the lee when the NW fills in. Avoid the Gulf Stream
in anything out of the north over force 3.
Cumberland Island is a must, and a short sail from St. Simon's. Make way down coast to at least Jupiter or West Palm/Lake Worth Inlet - even further south if you want. Wait for a good forecast
to cross, and enjoy a nice sail/motorsail across the G.S.
If you are going to the Bahamas - I think the best weather forecasts are from mwxc.com (free on SSB
subscription). I would highly recommend this unless you are very comfortable interpreting various forecast models in this area. NOAA forecasts don't really extend into the Bahamas - and computer models do have their limitations.
If you subscribe to the emails above - you will get good info about crossing the G.S. and weather in the Bahamas. He will also give you a tropical outlook (hurricanes) ahead of National Hurricane
center advisories. Hurricane
season is until Nov 30.
2. Other options? You could get a good window and jump across from St. Simon's, being sure to transect G.S. as fast as possible and sail onto Little Bahama Bank. But, more often than not it makes sense to hug the coast and get a good clear picture of what's ahead from the Nat. Hurricane Center before committing for the Bahamas.
3. To see all of the Bahamas, I would recommend first going to the Abacos - via Memory Rock/Little Bahama Bank - clearing in at Spanish Cay. Then head south to Spanish Wells/Harbour Island (take a pilot)/Eleuthera - then Cat Island/Exumas - Long Island
- maybe beyond. Don't really think the Berry Island are worth the detour - or Grand Bahama/Freeport - or New Providence/Nassau - San Salvador/Rum Cay for that matter. The Abacos and Exumas are most crowded. George Town is insanely crowded - so don't get stuck there with all of the cruisers looking for a weather window to the Caribbean
that never comes.
As far as how easy it is to get back and forth, most of the sailing is in the lee of the islands on the banks - so once in the Abacos - you will be in mostly calm conditions except for: 1) Whale Cay (south of Green Turtle Cay in Abacos); 2. 50 nm in NE Prov. Channel from Little harbour, Abacos to Eleuthera. 3. Exuma Sound - north and south of Cat Island. 4. If you decide to go to beyond Long Island
4. Best point of entry in Abacos is Spanish Cay via Memory Rock. If you decide to go across toward Berry Islands - Chub Cay or Great Harbour Cay are best.
There are lots to see and do - snorkeling: Pelican Cays Land & Sea Park Abacos; Exuma Land & Sea Park (Warderick Wells); Conception Island, outer reefs
on a calm day in Abacos, Eleuthera, Exumas, etc. Don't miss Manjack Cay, Abacos; Green Turtle Cay, Abacos; Harbour Island; Shroud
Cay/Ward. Wells, Staniel Cay, Little Farmer's Cay, Exumas; Fernandez Bay, New Bight, Cat Island; Conception Island; Clarence Town, Long Island.
If you arrive in late October, you will almost have the entire place to yourself. If you don't have it already, buy the Explorer Charts
of the Bahamas that are also the best cruising guide.
If you are entertaining going east from the Bahamas - it might be out of print, but get "A Gentleman's Guide to Passages South" by Bruce Van Sant.