Experienced Captain seeking local knowledge

It started in my reading chair in front of the fire. “Where should my summer cruise take me this year”?

Here are the parameters; I’ve got around 5-6 days to work with. I’ll be camp-cruising aboard my Eastern 21’ Pilot. I’ve got to factor in drive time trailering to a launch site.

The Chesapeake Bay’s been calling. I’ve visited the area supporting Boat Shows over the past few years. The possibilities look endless.

There’s always the Coast of Maine. I’ve been exploring its Bays, Rivers and Islands for the past 30yrs which I never seem to tire of.

What about something new? I threw another log on the fire. I’d been fortunate for time on the water. As a younger man I spent a decade as a freelance Capt operating a variety of vessels from Maine, down the East Coast, thru the Bahamas and the Caribbean as far south as Grenada. I threw in a trip around the Great Loop just for good measure (I’ll save the PNW and SE Alaska for another story).

What am I missing? As I study a chart of the East Coast, I’m reminded The Loop and several runs along the ICW took me down the Hudson River past NYC. Local cruising saw me as far as Rhode Island. I’m reminded there’s an area between Newport and NYC that’s not on my cruising resume.

I started to look more closely at Long Island and the Ct coastline with a new interest. I knew a lot of the names; Fire Island, the Hamptons, Montauk, and Block Island to the East. My summer cruising plans are starting to take shape.

I’m remembering an inviting launch site I’d visited several times in the Barn Island Wildlife area. Perhaps that could be my jump-off spot?

Any recommendations for a circumnavigation of Long Island? Where are the “must see” areas and anchorages?

I’d like to hear about any worthy sailors’ pubs along the way as well.

Help me plan my trip.