Nantucket

The Nautilus is the kind of place where the wine list is smarter than the context suggests — bold Italian and French classics on a pan-Asian menu in the middle of the Atlantic, somehow earning a Wine Spectator Best of Award of Excellence. Order off the beaten path here and you'll be rewarded; play it safe with the Napa Cab and you'll just be paying for the zip code.

The Brant Point Grill is Nantucket doing what Nantucket does — expensive, polished, and better than it has to be. The markups are real, but so is the depth, the staff knowledge, and the Domaine Leflaive waiting patiently for someone to order it right.

Oran Mor is a genuinely serious wine destination hiding inside a cozy Nantucket bistro — the list is deep, the producers are legit, and the Best of Award of Excellence is not a vanity trophy. Markup runs steep as it does everywhere on the island, but if you're picking a restaurant in Nantucket for the wine, you start here.

Topper's is the real deal — a Grand Award list that earns its reputation year after year on an island where easy money could have made this lazy a long time ago. The pricing will sting, but if you're going to splurge on wine anywhere in New England, this is where you do it.