Cruising North Fork, Block, Cape Cod

[DeaconBlues]

Need some local advice on planning a 3 week trip starting from Huntington Harbor. We want to do a few days at each of the following locations: Shelter Island and area, Block Island, Martha's Vineyard and Cape Cod. We believe we have enough time to allow for weather and we want to take it easy and be flexible on when and where we go in the area. No night sailing. The plan now is for me to take the boat up to Shelter Island between July 1st and 3rd and meet my wife there, stay a few days then head out to Block to begin the 3 weeks. We would like to do both mooring and slips with a few nights in hotels that have slips or moorings. Our draft is 5' and length is 40.
Biggest concern is getting reservations if we can. The weekend of the 4th will no doubt be the most difficult.