Like Hawaii, flip-flops and surf reports punctuate Montauk’s pace. Known as The End, Montauk sits 125 miles east of New York City at the tip of Long Island’s South Fork. Follow Route 27 through Montauk’s tonier sisters, the Hamptons, to reach the town, whose low-key vibe has traditionally attracted surfers, anglers, and artists.
Eat Smart: The Backyard restaurant at Solé East (631-668-9739) showcases locally sourced fish and vegetables as well as organic meats. The pan seared striped bass comes with a cauliflower truffle purée and a mushroom, tomato, and miso reduction.
Be Fit: You’ll find Air and Speed Surf Shop (631-668-0356) on Montauk Highway. This family-owned operation offers surf lessons, as well as board- and wet suit-rentals.
Live Well: At the Montauk Point Lighthouse (631-668-2544) visit New York’s oldest (commissioned in 1792) and still operational seafarer’s beacon. Gene Hughes was the last lightkeeper to tend the lamp, which became fully automated in 1987; you can tour the his lightkeeper’s house, now a museum.
Where to stay: Stick with the Hawaiian surfing theme at Surf Lodge ($275; 631-668-2632), where the telephone message greets callers with “Aloha” and signs off with “Mahalo.” The rooms, with doors painted in life-guard-stand-sized numbers, sport beds affording water views. Each opens onto a deck with a hammock. Classic surf films screen in The Den 24/7.