1. Montauk, NY
3 hours from NYC
Where to stay: Revel in the jaw-dropping ocean views from the tastefully appointed nautical-themed rooms at Gurney’s (pictured, $230–$348/night) for hundreds of dollars less than the going summer rates. It’s the sole year-round oceanfront resort in Montauk, so if you want to relive the wintry beach scenes from Eternal Sunshine of the Spotless Mind, this is your best bet.
What to do: Go on a Seal Walk at Montauk Point State Park ( $4) to observe up to four species of the wintering animals along the rocky coast, and then hightail it to check out Camp Hero, a mysterious, abandoned military installation that inspired Stranger Things.