is this a sight seeing trip or do you have a schedule ? Have you spent much time in the Out Islands of the Bahamas ?
If it were me and weather was accommodating, I would ... probably shakedown to the north coast of the DR, pit stop along here, then I would skip the T&C and do Inagua, Little Inagua, Plana Cays, perhaps Mayaguna if you need some supplies and/or internet, although not much there. Atwood Harbour on Acklins, definitely Landrail Point and if you can fit it in, a few days at Samana Cay, but make sure to enter around mid day, flat sea, excellent light, probably scout in ahead of the big boat with the dinghy.
If you go around the south end of Acklins, there is a loverly anchorage south of Salina Point on the west side, maybe a mile or two north of the point, which is a couple miles north of the lighthouse. Obviously only in easterlies. Continue from there north to the Fish Cays, then to Landrail. Or, make a run for the Jumentos, come around the very south end, try and avoid the Columbus Bank, it'll be rougher and bumpy, but not that bad, you probably will have to motor through it.
From Landrail, I would skip Rum, Clarencetown on LI is very nice and fun, Conception is a must.
If you go via Jumentos, spend your time in the southern half. The anchorages along Little Ragged are beautiful, you'll have it to yourself this time of year. Check out Duncantown, not much there. Hog, Double Breasted, Johnson, Raccoon are our favorites. From the Jumentos, you can either go to Georgetown via Hog Cay Cut if your draft is 6 or less, you can also go around the eastern end of Exuma near LI via the Comer Channel in more water. You can run up the Bank side behind Exuma from Jumentos to Black Point or Staniel Cay.
If you give me a bit more info, I might make suggestions how to get back to the States from Exuma regions, or at least what I would do !
Cheers, John