First time there... completely wowed. Ready to ditch the NE, and I would too, if it wasn't for my meddling kids... Rented a house, went on recommendations of the very nice people that we talked to and all worked out wonderfully. I tended to either stick with an appetizer or order 2 apps rather than main courses, which looked good but the apps looked better. Also, we were traveling with children and another family - 10 all together - and we weren't always organized to make reservations...
In the order that I remember, vaguely :
* Cold Beer at the ferry bar in Red Hook - St John Summer Ale, excellent.
* Morgans Mango - Pain Killer, excellent introduction to a very addictive drink, plus a very nice blackened chicken brie quesadilla - travel day so a bit foggy
* Breakfasts were all at home
* Lunches were either at the parks, or from Deli Grotto - the greek salad sandwich (forget what they call it) is extremely good beach food. The people working the Parks were better than the food but given that you're on the most amazing beaches in the world, it weren't so bad.
* the one lunch that wasn't either of the above was at Skinney Legs when we headed down to Salt Pond. Kids loved the burgers, cold Red Stripes, reminded me of Jamaica.
* Dinners - best dinner, bar none, il Dilivios (I think that's the name). The owners are quirky, very Italian (meaning, they make what they serve and you should eat what they tell you) and their English isn't so great - but MAN can they cook. Italian like I haven't had since Venice. Better than anything I've had in NYC or London. If they had an ocean view I would never have left.
* Asolare was really a surprise. I expected pretension, based on what I'd heard and read, but it was anything but. Killer Pain Killer. Really nice lamb, duck and tuna. Here I had an entree.
* Ocean Grill was better for lunch (I guess I forgot that day it rained) - jalapeno corn chowder is great, fish tacos and pork tacos excellent. Dinner was good, don't get me wrong, but better choices for the same $$$ in better locations. Good pain killers...
* ZoZo's could serve me just about anything at sunset. Here's where my app strategy paid off best - nice bottle of wine( Amarone), killer freshettas and antipasto. No report on their pain killers, the only place I didn't have one...
* Morgan's, the Fish Trap, Lime Inn - all decent and worth the money, all exceptional pain killers.
* Woody's for walk up drinks but that's it. TIP: don't park on the sidewalk in front, even if you're just running in to grab a drink. Makes for a difficult explanation to the officers. Or so my brother-in-law says...
* Had a great pizza from Cafe Roma. When we picked it up, made a mental note to try the place next time I'm there and it rains.
Didn't want to try the drive back from Chateau. And none of us were bright enough to think of taking a cab.