From my experience, the only other place to provision other than Roadtown was Spanish Town. The prices are higher.
I would stock up at Bobby's which can be done online.
Eating out every night is very doable. Did that last time. Willy T's, Bitter End, Anegada, Cooper Island, Last Resort. (5 day power boat course.)
ISPA Yachtmaster Offshore Instructor Evaluator
Sail Canada Advanced Cruising Instructor
IYT Yachtmaster Coastal Instructor
ASA 201, 203, 204, 205, 206, 214
As I sail, I praise God, and care not. (Luke Foxe)