Travel time: 1hr
What to bring: That Vineyard Vines
Best for: Preps and bros

Admittedly, your best bet is to fly to Nantucket. But the good news is, it's a short, inexpensive—and might we add, direct—fight, and it's well worth every penny. Of course, once you get there, be prepared to spend a little bit of dough. Just so there's no confusion here, yes Nantucket is in Mass., meaning you're going to be surrounded by Red Sox and Patriots fans. But to be fair, they're easy going people, so don't feel like you're betraying your beloved NY teams.

If you want to do Nantucket right, rent yourself a jeep and hit up one of many off-road trails and beaches on the island. Perhaps even rent a beach cruiser if you really want to blend in. But whatever you decide to do, make sure you pack your best Carlton outfit because it's one of those places dudes rock polo's with sweaters draped around the shoulders. A place like Nantucket, you expect the highest quality food and drink. Fortunately, it doesn't disappoint. If you want the best lobster you've ever had, head over to Cru, a waterfront restaurant that will make you feel real special. And if you happen to be on the island mid-June, you might even catch Ben Stiller or Brian Williams showing face at the Nantucket Film Festival. There are some solid breweries on the island that are worth a visit, too.