1. Where to Stay
Watch Sunday-night surf movies beside the outdoor fire pit at the Surf Lodge (from $350), a hotel known for its social vibe and summer concert series; acts like the Like (June 26) and Daniel Merriweather (July 10) play every weekend on the deck overlooking Fort Pond. In July, a food stand will supply fish tacos and lobster rolls to late-night revelers until 3 a.m.
Unwind in the pristine, all-white rooms at Solé East’s Resort (from $210), where the seven garden cabana suites were renovated last year. Listen to the mellow, beachy tunes of the on-site D.J. from your lounge chair or yoga deck in the landscaped garden.
Admire unobstructed views of Lake Montauk from your private balcony at the Montauk Yacht Club Resort & Marina (from $279), fully renovated for its 80th birthday last summer. The nautical theme carries throughout the hotel, from the navy-and-white-striped room décor to the hour-long deep-tissue “yachter’s massage” ($125) at the spa.
2. Where to Eat
Arrive at the month-old Navy Beach by 5:30 p.m. to commandeer a picnic table overlooking Fort Pond Bay. The coastal comfort food, like crab cakes, lobster rolls, and burgers ($15 to $31), is served in a space adorned with vintage fifties beach photos.
Call the day before to reserve a table facing Lake Montauk Cove at the Crow’s Nest restaurant (4 Old West Lake Drive; 631-668-2077), upgraded in June 2010 to emphasize the water views and locally sourced, Mediterranean-inspired seafood menu ($10 to $32). Star hotelier Sean MacPherson (of the Bowery and Jane hotels) is poised to gut-renovate and reopen the restaurant and adjoining fourteen-room inn for summer 2011.
Nurse a glass of wine ($10 to $12) at the new cocktail and appetizer lounge on the outdoor patio of Montauk classic Dave’s Grill, renovated in May 2010. Go for chef-owner Dave Marcley’s revered lobster roll, made with a half-pound of knuckle and claw meat—never tail meat—poached in warm butter and served on toasted brioche ($34.95).
3. What to Do
Browse cutout swimsuits, gingham wedges, and customized pastel-banded Meyerhoffer surfboards ($2,000) designed by Montauk resident Cynthia Rowley at the surfer-girl-themed store she opened next to the Memory Motel in May. The boutique will host a rotating lineup of limited-edition pop-up shops this summer, including Lauren Bush’s not-for-profit FEED Projects on June 24 and Chrissie Miller’s Sophomore label on July 14.
Stock up on hard-to-find apparel from Rogan’s Loomstate for Surf Lodge capsule collection at the Store (183 S. Edgemere Street; 631-668-8131), a new whitewashed boutique unveiled over Memorial Day weekend. The line’s photo-print hoodies ($149) have already sold out at Bloomingdale’s.
Troll stacks of rare sixties- and seventies-era T-shirts—a vintage Rolling Stones tee is $250—decal-covered jean jackets, and paint-splattered Carhartts at Melet Mercantile (102 Industrial Road; 631-668-9080), a stylist’s paradise of clothing and collectibles opened by former Ralph Lauren vintage buyer Bob Melet last summer. Hidden within an unmarked metal shed, the stash ranges from $8 handmade mariner’s-rope bracelets to a French foosball table from the twenties ($9,500), with inventory replenished on a weekly basis.
4. Insider’s Tip
Prime beach parking is the hardest thing for weekend visitors to find—especially near surfing mecca Ditch Plains—as most spots require a resident permit. The best little-known option for day-trippers is the parking pass at the East Deck Motel, a one-story fifties ranch with a small lot that’s steps from the top surf beach ($20 on weekends, $15 on weekdays).
5. Oddball Day
Kick-start the day at Coffee Tauk, a highly caffeinated, month-old espresso joint where all the baristas have more than four years of training. Order the New Orleans iced coffee, made with chicory, sweetened whole milk, and beans that have been cold-brewed for twelve hours ($2.50). Head half a block east to Naturally Good Foods & Café for vegan and organic brunch fare like mango raspberry scones (baked in-house) and egg breakfast tortillas ($4.95). Walk off breakfast a half-block south along the Atlantic, then circle back for an hour-and-fifteen-minute class at the month-old Love, A Yoga Space ($18), where artful graffiti covers the walls and a corner hammock invites post-class lounging. Test your newfound sense of calm with a surf lesson by Love’s in-house pro Mikey DeTemple, the 2009 East Cost surfing champion, at the Dirt Lot at Ditch Plains ($150 per hour, boards provided), or opt for a two-hour stand-up paddleboarding tutorial along the Western part of Lake Montauk with Gina Bradley, a.k.a. the Paddle Diva ($150; like kayaking, but standing upright on a long board). Afterward, order a round of shrimp tacos on blue corn tortillas at Montaco (follow their tweets for location @montacotruck), a fuchsia-colored taco truck that will be pulling up to Ditch starting July 4, and watch the pros ride the waves. Cap off the day with Pirate Juice cocktails (a mix of spiced rum and ginger beer, $8) at the Montauket for the sunset views over Fort Pond and a mix of Montauk weekenders and locals.
Fishbar restaurant’s blog, freshlocalfish.com, has great advice on where to eat in town.
Check the daily surf conditions and live beach webcam at surfline.com.
Montauk’s Chamber of Commerce lists hotels and less expensive motels (from $65), plus a calendar of cultural events.
Pinpoint the latitude and longitude of the best Montauk fishing spots at marinebasin.com.