|Claudio's in Greenport, NY|
However, let's start here, with a history that's truly incredible, dating back to 1870. Considering some restaurants have trouble staying open more than three years these days, that kind of longevity is very impressive.
At the risk of being chided, I would venture to describe Claudio's crowd as 'wealthy biker,' as in, if a tattooed twenty-something motorcycle crew had millions of wall street dollars in the bank, they would party at Claudio's. I've never seen so many million-dollar go-fast boats in my life, and I've never seen a group of boat owners so young. From this, I surmised two things: first, if I were going to choose between riding a $12,000 Harley or a $1,000,000 Cigarette boat, I would choose the latter. Second, I missed something in my hunt for a career, because whatever these guys (they were all guys) do for a living, I want to do it too. The sooner the better.
With oysters for $2 apiece and the best specialty drink I've ever tasted (and I don't even like mudslides!), this is a must-visit spot for Long Island travelers. The group seemed mostly of a Connecticut persuasion. However, the deck-party atmosphere with live music, a bustling bar, a Miami yachting scene, and a view that you could romance all day signified that Claudio's can only be a child of Connecticut's much cooler older sibling, New York. Sorry, CT, but you're just a bit more conservative. And I don't take 'yachting scene,' lightly either; I mean what I write, with a few 90+ footers rolling in to frolic with the rest of the boats.
For a quieter time, head across the docking canal to Crabby Jerry's, where food and drink is similar (and the staff is friendlier and not as rushed), and the 'view' is more subdued. Read: a reduction in bikinis, tattoos, and music. That can either be a good thing or a bad thing, depending on your hangover from the night before.
So, the next time you're wondering where to go, and the Mystic Seaport Museum just won't do it for your post-collegiate party crew, head over to Claudio's - it's an easy 35 minute ride from Old Saybrook, give or take a Cigarette boat versus a trawler, and going with or against the tide. In any case, once you get there, there's no doubt you'll be going with the flow.