Distance and drive time: 160mi, 3hrs 30mins
A sunset sail aboard Schooner Hindu (Key West Bight Marina, Margaret St; 305-509-1771, sailschoonerhindu.com) combines many of Key West’s greatest pleasures: boating, those famous pink skies and outdoor drinking. Before your night spirals into a blurry good time on Duval Street, take in the island’s offshore beauty aboard a charming restored wooden boat. You’ll want to ease into the hard-hitting fun this slow-moving town is known for.
Eat: By husband-wife duo Tommy Quartararo and Kristen Onderdonk, Little Pearl (632 Olivia St; 305-204-4762, littlepearlkeywest.com) is a hit with critics and people in the neighborhood. Stick out the wait for a chance to taste one of the city’s most creative seafood menus, featuring comfort food classics like the lobster and crab pot pie.
Drink: Just one block south of Duval Street is the Green Parrot Bar (601 Whitehead St; 305-294-6133, greenparrot.com), a local watering hole with live music, a great jukebox, trippy decor, pool tables and a crowd that spills onto the sidewalks as the night goes on. Around these parts, the drink of choice is a round of Boot Beer Barrels—a shot of root beer schnapps plunged into a rocks glass of Miller Light. Now, chug!
Stay: To experience the hipster side of the island (yes, that’s a thing), check into Oceans Edge (5950 Peninsular Ave; 305-809-8204, oceansedgekeywest.com), a luxurious resort on Stock Island, which is considered the “old” part of Key West. The shipyards, shrimp boats and artist studios in the area are cool once again.