SI Swimsuit’s Official Guide to Montauk

Found roughly two and a half hours outside the hustle and bustle of New York City, Montauk proved to be the perfect beachy backdrop for a selection of models featured in SI Swimsuit’s 2026 issue. The location shone through in every snapshot courtesy of the town’s vintage feel, fun-in-the-sun activities and warm, welcoming vibes.

Merging 1950s flair and modern amenities, the quiet coastal town is a must-visit for those seeking to switch things up on their next vacation. Whether you’re a foodie looking to dine at a local favorite or an adventurer looking to tackle your next great hike, Montauk, N.Y., truly has something for everyone.

Where is Montauk?

This coastal oasis is located on the easternmost tip of the Long Island peninsula in New York, in the Town of East Hampton. For those traveling from out of state, the Hero Beach Club—who hosted SI Swimsuit for the 2026 issue—is approximately two and a half hours from John F. Kennedy International Airport and about three hours from LaGuardia Airport. From there, the location is accessible by car, via the Long Island Rail Road to Montauk Station or the Hampton Jitney.

Where to stay in Montauk

While in Montauk to shoot the 2026 issue, the SI Swimsuit team and featured models stayed at the Hero Beach Club. Originally built in the 1950s and located just off Umbrella Beach at 626 Montauk Highway, the hotel offers an effortless, laid back vibe right on the water. The hotel boasts a boutique experience for travelers, with only 30 rooms available—including Hero Queen rooms with partial ocean views to multi-bedroom suites for families or groups—creating a more intimate, close-knit community feel while balancing “bohemian spirit with surf culture.”

Surfing, fishing, biking and more outdoor activities are available for those with an adventurous side. Meanwhile, its proximity to the Atlantic Ocean allows those more interested in lounging in the sand with a good book to make the most of the location. Depending on the season, you might even be able to catch a yoga or pilates class, which they hold on the hotel’s lawn.

According to the Hero Beach Club, all stays include a welcome drink upon arrival, daily continental breakfast, heated pool access, full beach setup with attendants, complimentary bikes and soft-top surfboards, seasonal fire pit gatherings with s’mores kits, daily wellness classes (depending on the season) and sauna/steam room access. While rates vary by season, a stay during the peak summertime will have prices starting at $800+.

What to do in Montauk

Eastbound Surf Club: Ever dreamed of catchin’ a wave and hangin’ 10? Well, the Eastbound Surf Club has trained instructors on hand, ready to help make those seaside skills a reality! Whether you’re looking for private lessons or coaching, they offer something for every age and skill level, with appointments available for booking through the summer months.

Montauk Wild Oysters Co.: Oyster lovers will find their calling at the Montauk Wild Oysters Co., which invites seafood fans to try their hand at shucking the oceanic delicacy. With options for Oyster Shucking Masterclasses and Oyster Foraging and Snorkeling, get up close and personal with all the work that goes into one of the East Coast's favorite meals.

Farmer’s Market: This seasonal option is available through October, allowing visitors to check out some unique small businesses in the area. Breathe in that salty seaside air while you stroll around the vendors selling freshly baked goods, homemade sides and even small batch sangria.

Gurney’s Montauk Resort & Seawater Spa: Alternatively, if you’re looking to make your stay in Montauk one of true relaxation, you won’t want to miss the offerings available at Gurney’s Montauk Resort & Seawater Spa. While the resort itself is another great option for your stay, the spa options set the location apart. Enjoy a “true multi-dimensional thalassotherapy wellness experience” in The BathHouse or detoxify with a High Performance Facial and Sea & Salt Glow Body Scrub.

Sights to see in Montauk

Montauk Point Lighthouse: It truly doesn’t get more East Coast than a lighthouse adventure, and the world-famous Montauk Point Lighthouse is one of the very best. Located at the very tip of eastern Long Island, the structure boasts “unforgettable 360° views over the Block Island Sound, the Atlantic Ocean and points west.” According to the Montauk Historical Society, it’s also one of only 12 lighthouses to have been named a National Historic Landmark.

Walking dunes: If you’re the type to enjoy a nice hike while on vacation, the walking dunes are likely already calling your name. During their trip, the SI Swimsuit team noted that the space is “like the Sahara desert but on the bay,” providing visitors with grid-worthy photos guaranteed to make your trip one you’ll remember long after you return home.

Where to eat in Montauk

Ditchwitch: Located at Ditch Plains right by the beach, Ditchwitch is the definition of a local gem. The seasonal spot opens its doors in May for the summer, offering a selection of seaside poke bowls, burritos, breakfast items and more.

Joni’s: Serving up pure deliciousness since 2001, the eatery describes itself as a “come one, come all clubhouse.” You’ll find a little something for everyone on the menu, which includes salads, sandwiches, smoothies and more. Joni also released a cookbook this year, allowing fans far and wide to savor the flavor of the shoreline spot at home. Learn more here.

John’s Drive In: If you’re craving a burger and fries, look no further than this classic drive-in. First opening its doors in 1967, the location will make you feel like you stepped back in time. And as if that’s not enough of a reason to visit, they also offer an array of ice creams, shakes, cakes and more sweet treats to finish your day the right way.

Monte’s at the Manor: Built in 1920 by Carl Fisher—who built Miami Beach and Montauk—this local gem can be found inside Montauk Manor, and has some seriously stunning views of the sunset. Offering breakfast, dinner and “lite bites,” there’s definitely something on the menu for everyone. Their Italian fare is so popular that their “Original Family Recipe Tomato Sauce” is even available for sale.

Dive Bar Pizza: A casual pizzeria located on the docks, Dive Bar Pizza is the ideal Montauk spot to enjoy a cold drink and a warm slice. On the menu, you’ll find go-to classics like cheese and pepperoni, as well as a few favorites specific to the beachy location, like “Grandma Pie” (Square pie, crushed tomatoes, mozzarella and garlic) and “White Clam.”

Navy Beach: Located on a private beach for the ultimate Montauk experience, this picturesque option offers “casual coastal cuisine complemented by an eclectic wine selection.” Grab your own individual lunch or dinner, or bring your family and friends and preselect shareable options from their special “family-style menu.”

Montauket: During their visit, the SI Swimsuit team specifically noted this classic Montauk restaurant and bar was “one of the best places to watch the sunset.” Once you finish your delicious meal, be sure to check out the vintage shop onsite!

The Bird on the Roof: If you’re someone who lives for a good brunch option, The Bird on the Roof is a must for you! With classic brunch menu items like French toast and egg sandwiches, to a dinner menu that merges “Japanese ingredients and French technique,” your next favorite bite is waiting for you.

FAQs for your trip

When is the best time to visit Montauk?

The answer is: it depends on what type of experience you’re hoping to enjoy! If you’re looking to stay on the shoreline during the slower, more laid back season, we’d suggest staying during the “off season” in the fall and winter. However, if you want to get in on the action and join the hustle and bustle of a summertime staple location, you can’t beat Montauk in May through August for their peak season.

What are the packing essentials?

As with any beach destination, we’d recommend you take your favorite reef-safe sunscreen. Still, don’t stop at just that for sun protection, as you should also always have a wide-brim hat and some sunglasses on hand. Depending on your planned activities, pack accordingly. Going on a hike? Make sure you have your most comfortable walking shoes with added support. Want to try your hand at surfing or snorkeling? A comfortable swimsuit and/or wetsuit will be a must.