Alright... Just about 2 weeks until setting sail on July 24. Thanks to everyone for the input and advice! After lots of talk with the Mrs. we are going to try to get to Block Island at the end of the trip as neither of us have been before and not sure when we will get back to the area.
All updated plans are crew temperament (wife and our 6 & 3 year old boat bums) and weather/conditions permitting. I have incorporated currents into the plans to the best of my knowledge, but I think we still have decent wiggle room with a mix of time ashore and underway. Currently, for the 11 day cruise there will be 3 days with sails between 30-40nm. Plan on doing a lot of exploring via dinghy at most locations and splitting grilling/cooking aboard and eating out somewhat evenly.
July 24 Day 1 - Depart Warwick in the late afternoon with boat loaded and provisioned up and head to Potters Cove for evening on the hook.
Day 2 - Depart Potters Cove in the morning for Cuttyhunk via Sakonet River in the AM with a favorable current downriver.
Day 2-5: Cuttyhunk and Hadleys. 3 nights between the two, likely with 2 in Cutty and 1 in Hadleys.
July 28 Saturday Day 5: Hadleys to Vineyard Haven. Max flood is approx. 1000 with slack at noon, so figure on hitting the straight at 1115-1130. If someone can give me a sanity check on that, it would be appreciated
Day 5-8: Vineyard Haven and Menemsha. 3 nights between the two, likely with 2 in Vineyard Haven and 1 in Menemsha.
Day 8: Sail from Menemsha to Block in the AM. This could be pushed to day 9 if weather isn't cooperating. If it really doesn't cooperate, will likely change plans to scrap Block and spend some more time on the Vineyard, with a stop over back in Cutty and something else before heading back toward Warwick.
Day 8-10: Block Island. It will be mid week, so hopefully can find room to drop the hook and avoid paying for a mooring ball each night.
Day 11: Sail from Block to Warwick... potentially sneak in one more night aboard somewhere such as Dutch Harbor if we can bring the boat back the following morning.
Saturday 8/4 - drive back south to MD and count down to fall sailing on the Chesapeake Bay!