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Weekend in Nantucket- Restaurant recommendations needed

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I'm heading to ACK for the first time the weekend of September 19-21. I would love some restaurant recommendations. My husband and I will eat about anything and cost, if worth it, is not an issue. For dinner, a place with a nice reasonable wine list is nice, but a well made manhattan would be better. If there are any small plate places, those recommendations would be very welcome as well as places for pre-dinner drinks and the raw bar, if different from other restaurant recommendations. Also, will the island still be crowded that weekend and will I need to make reservations far in advance for that weekend?

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  1. My personal favorites are Topper's, Brant Point Grill and the Sconset Cafe. The best lunch/sandwich place is Something Natural.

    1. Go to Brant Point Grill on Friday, 2:30-4:30, for the buck-a-shuck oysters...sit and look out at the harbor. Rain or shine, it's great. The menu also has bucket of peel & eat shrimp and fried calamari. All a great deal that won't break the bank. I'd skip Sconset Cafe. You can also grab some light bite/small plate apps at The Proprietors on India St (formerly DeMarco's) before heading to your real dinner. The Galley is great if money is no object. On the beach past Jetties Beach. You are paying for the view and ambiance. I love Queequeg's (downtown behind Ventuno) and Center St Bistro (BYOB!!). Agreed that Topper's is a top notch spot: beautiful grounds and great service (expensive, but worth it for a few drinks and the experience).

        1. Thank you both for the recommendations! Very much appreciated!

          1. Glad I came across this post! I'm headed up this weekend for a wedding and was looking for a few recommendations. Any recommendations for some interesting bars? I've been up only a handful of times and honestly can't remember the names of the bars I've been to. My husband mentioned something about a bar in a railroad car? Is this true?

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            1. Just got back a couple weeks ago from a night in Nantucket. We started with lunch at Galley Beach. Food was pretty good. Very pricey. You are paying for the the setting and view which was outstanding. I'd definitly go back on a nice sunny day. (I think this may be the same as "The Galley" recommended in another post already).
              We followed that with dinner at Oran Mor. Definitely one of my favorites out there.
              Breakfast the next day was Black Eyed Susans followed by lunch at Straight Wharf. Lunch was very good, but it was a smaller limited menu which was only served at the bar & back patio. They don't open the full restaurant for lunch; I had been hoping to sit in the larger restaurant section overlooking the water, which you can do for dinner.

              1. Just spent the weekend and my favorite was Languedoc. From ambiance to food to service it was perfect. Could be the best grilled quail I have ever eaten. Others were OK, nothing special so I would not recommend as highly. Don't forget the Juice Bar for ice cream, the chocolate chocolate chip was outstanding but the banana was a little weak.