If you can't figure out what to do in a remote spot then it is pointless for someone to explain - and I don't mean that in an unkindly way. There are some people (a few) who just like to sail and only stop briefly before carrying on. I can think of a boat from our yacht club that went to Bermuda years ago. They cleared in and then went and anchored. The crew got ready to go ashore for dinner and a dark and stormy or three and asked the captain if he was coming along. His answer was, 'No, I've been here before'. They stayed for four or five days and then headed back home. Remember this is a trip to/from Lake Ontario so mast down and up twice and going through the Erie Canal and Hudson twice. Not a casual undertaking.
Sounds like you should just pick the routes and timings that give you the best sailing with stops only to do repairs and provisioning.
Sounds like you should just pick the routes and timings that give you the best sailing with stops only to do repairs and provisioning.