EAT & DRINK
668 The Gig Shack 782 Main St (631-668-2727, 668thegigshack.com). Run by a local mom and her three surf-bum sons, this relaxed café serves elevated seafood fare (soft-shell crab BLT, $16) and eclectic global cuisine (duck empanada, $12). All baked goods—from homey red velvet cake to gooey Montauk mud pie—are made onsite, and if you don’t want to waste precious tan time, you can pack a picnic and walk to the beach from here. On weekends, the space hosts live acoustic guitar and jazz musicians.
Inlet Seafood Restaurant 541 E Lake Dr (631-668-4272, inletseafood.com). Fish just doesn’t get any fresher than this: Owned by six Montauk commercial fishermen, the eatery’s seafood comes straight from their boats, is usually caught that day and gives true meaning to the term “locally sourced.” Arrive around dusk and you’ll be treated to a glorious sunset over the harbor, plus unique sushi rolls like the Angel Eyes ($18), made with spicy lobster, cuke and avocado, and a blue claw California roll ($11), to break the tuna roll doldrums.
Second House Tavern 161 Second House Rd (631-668-2877, secondhousetavern.com). Housed in a century-old building, this bistro is closer to home than you think: The kitchen is helmed by Richard Soriano, late of Park Avenue Café, and the more casual Grill Room reserved for walk-ins is furnished with salvaged wood from an old Lower East Side building. Low-key grub like thin-crust pizza and Black Angus burgers is paired with inventive cocktails (the signature Second House Cider blends rye with apple cider and ginger ale) and comes with waterside views of Fort Pond Bay. For $30 extra, you can pair wine or beer with the chef’s four -ourse tasting menu.
Havana Beach Club 448 W Lake Dr (866-377-8132, havanabeachclubny.com). One of the few area Cuban restaurants, the dining room here skews classy, serving oxtail with rice and beans on tables dressed with teal linens. For the flip-flop-wearing crowd, grab a seat on the outdoor patio or hit the walk-up window for Cuban sandwiches. Even better: You can grab to-go cups of flavored mojitos.
Harvest at Fort Pond 11 S Emery St (631-668-5574, harvest2000.com/hfp). Reservations at this year-round restaurant can be difficult to nab, although you should expect a wait even if you do score one. If you’re really lucky, you might be seated outside in the herb, vegetable and flower garden, where you can dine among the origins of your meal. Come with a group to share the enormous portions of fish, ribs and pasta.
WHERE TO STAY
Surf Lodge 183 Edgemere St (631-668-3284, thesurflodge.com). $275–$400 per night. This sceney hotel-bar-restaurant from the club impresarios behind Cain single-handedly put the sleepy fishing village of Montauk on the party map. Between the locally sourced cooking of Top Chef season-two contestant Sam Talbot, musical acts like Julian Marley, Ben Sollee and Matt Costa performing at the outdoor lounge overlooking Fort Pond, and classic surf films being screened at all times in the library-like Den, there’s constant action going on, and it draws a crowd. Thankfully, the hotel’s a half-mile from the beach, so you can easily rent a kayak, canoe or bike and get out of dodge.
Montauk Manor 236 Edgemere St (631-668-4400, montaukmanor.com). $275–$620 per night. Make yourself at home in one of the apartment-like rooms, ranging from studios to three-bedroom suites, at this English Tudor–style condo-hotel. Built in 1927 by industrialist Carl Fisher, its perch atop Signal Hill affords views of Gardiners Bay and the Block Island Sound (which can be spied from the privacy of your room’s own balcony). The 12-acre property hosts a hot tub, sauna, squash and tennis courts and one of the few indoor pools in Montauk (albeit a shallow one).
Montauk Yacht Club Resort & Marina 32 Star Island Rd (631-668-3100, montaukyachtclub.com). From $229 per night. Celebrating its 80th anniversary this year, the recently renovated full-service resort has a long legacy of catering to the rich and famous (founding members included J.P. Morgan, Vincent Astor and Harold S. Vanderbilt). Each of the 107 rooms and 5 private villas offers views of Lake Montauk, where aviator Charles Lindbergh would often arrive by seaplane—although you might want to make your entrance via the 23-slip marina.
WHAT TO DO
Ditch Plains Off Ditch Plains Rd. Famous for its surfing, the consistent, beginner-friendly waves are also alluring to longboarders looking to hang ten. Fuel up on breakfast burritos and the sesame-noodle salad from takeout truck Ditch Witch, parked in front of the East Deck Motel, before you paddle out.
Montauk Downs State Park 50 S Fairview Ave (631-668-5000, montaukdowns.org). NY State residents $19–$41. Robert Trent Jones designed this well-maintained 18-hole golf course, and because it’s public, it’s inexpensive to play. There’s also an Olympic-size swimming pool and six tennis courts on the grounds.
The Montauk Point State Park 50 S Fairview Ave (631-668-3781). $6 per car. It’s not just nature walks and gorgeous views at this wildlife preserve (although when the water is calm, you can see as far as Rhode Island). The easternmost tip of Long Island is also where you can visit the historic Montauk Lighthouse, the state’s oldest, and go surf fishing—no permit necessary.