Road trips
Duval Street KEY WEST 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: The latest by husband-wife duo Tommy Quartararo and Kristen Onderdonk, Little Pearl (632 Olivia St; 305-204-4762,
littlepearlkeywest.com), which opened in February, 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!
Time Out Miami May 18–August 16, 2017 Little Pearl
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.
Osteria Tulia NAPLES DISTANCE AND DRIVE TIME: 125MI, 2HRS
Nestled between the pristine Gulf of Mexico and the gritty Everglades, Naples is not your typical beach town. Stroll down the neatly landscaped Mediterranean Revival–style downtown district, where you’re most likely to spot snowbirds. Shed some layers for a walk down the rough-and-tumble Fifth Avenue South, and join locals hoisting longboards en route to the beach. Whatever your seaside style, you’ll find it in Naples.
EAT: On the off chance you’re carbo-loading at the beach (this is vacation), Osteria Tulia’s regional Italian menu is full of reasons to indulge (466 Fifth Ave South; 239-213-2073,
osteriatulia.com). Work your way through the list of artfully prepared small plates, like the caramelized sprouts and crispy fried pig
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PHOTOGRAPHS: TOP LEFT, TOP SPREAD: SHUTTERSTOCK; CENTER RIGHT: COURTESY CC/YELP/FOODIEK; CENTER: SHUTTERSTOCK; CENTER BOTTOM: COURTESY CC/YELP/JERRYR
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