A longtime breakfast favorite, Joni’s carries in crowds as colorful as its turquoise walls. Namesake owner Joan Brosnan takes great care to adjust the menu seasonally, bringing in fresh choices with wacky names like “y u crabby?”—the scrumptious crab cake sandwich Joni recommends to liven up a Wednesday lunch hour. Guests brace the eternal queue for custom breakfast sandwiches, “all fresh fruit” juices, smoothies made-to-order and veggie burgers. Phone: 631-668-3663 | Address: 28 S Etna Avenue #9
The East End extension of Swallow in Huntington, this New American spot features elevated small plates. Favorites on the menu include “mac & cheese” with orzo, peas, bacon and asiago cream sauce, coconut curry mussels and asparagus fries. Can’t decide on just one plate? Don’t worry—sharing is caring at Swallow East. Phone: 631-668-8344 | Address: 474 West Lake Drive
The people behind Tacombi got their start selling tacos out of a VW Kombi bus (hence the name) along the sandy shores of Mexico. The refreshing Mexican fare capitalizes on the freshest catch you can find at The End, playing off the traditional Yucatan recipes that started it all. Phone: 631-668-8338 | Address: 752 Montauk Highway
The pastel cans can be found all over the Island, but why not stop in at LI’s easternmost brewery? Founded by three buddies in a basement in 2012, this craft brewery has evolved to reflect the simple yet active lifestyle of their namesake town. Their red brew barn in Montauk invites craft beer lovers to “come as you are” and sip on the likes of the Wave Chaser IPA. Phone:631-668-8471 | Address: 62 South Erie Avenue.
Spend a day on the water with one of Montauk’s world-class boat fleets. Venture into the Atlantic for a fishing expedition, spend an afternoon sailing or relax on a boozy boat cruise around the Sound. Whatever you’re up for, the likes of Viking Fleet (speed boats) and Catamaran Mon Tiki (sailing) will help you cruise the day away.
What would a trip to Montauk be without a pitstop at the classic landmark at The End? Through a 360-degree panorama of the Block Island Sound and Atlantic Ocean, climb to the top of this over two century-old structure for the best view on the Island. And while you’re there, enjoy the museum in the old lighthouse keeper’s residence, displaying history like George Washington’s signed authorization for the lighthouse in 1796. Phone: 631-668-2544 | Address: 2000 Montauk Highway.
Hang ten in the Hamptons’ sleepy surf town with a little help from the resident best: Corey Senese. The SoCal transplant who spent his summers in Montauk growing up has constructed a knowledgeable team of lifetime surfers to have even the earliest of beginners riding waves in no time. Whether you’re looking to improve your surfing skills or just have a fun afternoon activity, Coreyswave guarantees classes that are safe, informative and—most importantly—fun. Phone: 516-639-4879.
Where to Stay
This Montauk mainstay has evolved over its 90 years in business into The End’s only oceanfront resort destination. Having just completed a multiyear renovation of the entire property, the property features both traditional hotel rooms and “cottages” that include a kitchenette and feature exclusive access to the resort’s private beach. Spend the afternoon at the stunning indoor saltwater pool overlooking the ocean, a Russian steam room and Finnish rock sauna at the spa and—of course—relax by the water in one of the cabanas for rent. Phone: 631-668-2345 | Address: 290 Old Montauk Highway.
This beachfront property right on the Block Island Sound—as the name suggests—is a perfect home away from home for the summer. You’ll find 25 spacious studios under its beachy blue roof with full kitchens and plenty of beds for the kids. Swim laps shoreside in its heated pool, lounge on the neighboring beach or take the short hop to town to enjoy the bustling Montauk scene. No matter what’s on the schedule, consider this a worthy home base. Phone: 631-668-5500 | Address: 6 Soundview Drive.
This expansive property is the ideal backdrop for a weekend away in Montauk. The grounds feature a garden made for the events the hotel puts on weekly—from clam bakes to movie nights—just steps away from stunning Umbrella Beach. Hero also offers an exclusive buyout option for full control of the grounds during your party’s stay. And what weekend out East would be complete without a private pool oasis? The one here is outfitted with custom furniture from Bali, making it the perfect perch of relaxation. Phone: 631-668-9825 | Address: 626 Montauk Highway.
For a taste of history in your hotel accommodations, the restored vision of 20th century developer Carl Fisher’s “Castle on the Hill” is a splendid choice. Its tutor-style exterior only hints to the grandeur of its interior, as you walk the open halls roofed by its exposed wooden beams. All the luxury of a hotel is combined with the convenience of condominiums on this 12-acre property, complete with two pools, a spa, tennis courts and the delicious La Fine Italian restaurant. But the pièce de la résistance of your stay will be the views—and you’re getting all of them: the Atlantic Ocean, Gardiner’s Bay and the Block Island Sound. Phone: 631-668-4400 | Address: 236 Edgemere Street.