Join Date: Feb 2010
Location: Narragansett Bay
Thanked 541 Times in 518 Posts
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Re: Hello from CT
Welcome. I grew up on my parents boat in Western LIS. I fondly recall some Father/Son trips we took from there to Block, when I was very young. Block was much quieter back then. The Oar had no windows. Still, I love Block in mid-Sept, I avoid it in Jul and Aug. You have to go through the Race, however, so be sure you understand that. You don't want to cross wind and current there. Going through Fisher's Island Sound is an option, but less direct.
While there are no haul out boat yards, it's very much a boating vibe, especially in New Harbor. It's a great adventure.
Nevertheless, there is plenty to do in LIS. We vacationed quite a bit on Fisher's Island back then. Its super quiet, with very little tourist infrastructure. The Yacht Club does take transient reservations now. The one bar/restaurant will be on the verge of closing for the season by then. Grocery store. There is even a boat yard, owned by the DuPonts. Yes, those DuPonts. They owned most of the island over 100 years ago.
Personally, not a big fan of Shelter Island. Greenport either, but most do like it there. You might consider Montauk, but it's just as big a commitment as Block. Mystic Seaport is a neat idea. Get a slip and you get access to the museum all night. One of my fav locations as a kid was swinging on the hook in Eaton's Neck. You could go ashore and set up a beach bbq back then, but I think I've heard that's restricted now.
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