NEWSLETTER
This article was originally published on 04/26/2018 and last updated on 05/14/2026.
FRIDAY
4 pm: Make a pit stop for some seafood
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After you’ve passed East Hampton, you’re in the home stretch of your trip to the tip of Long Island’s South Fork and almost to Montauk. Before you get into town, you’ll pass two classic seafood shacks practically across the street from each other: The Lobster Roll and Clam Bar at Napeague (both open seasonally). Stop at either one and get your first taste of fresh seafood to start your weekend right, whether it’s a succulent lobster roll, a lobster BLT, a dozen local oysters, crispy strips of fried clam, or even an early dinner with a catch straight off the day-boat.
5:30 pm: Check into your hotel
Credit: @where.do.you.summer on Instagram
Montauk hotels have grown increasingly chic as the area has evolved from quiet beach town to luxurious getaway. In season—between Memorial Day and Labor Day—you’ll pay top dollar whether staying in a small motel or at the famed Gurney's Montauk Resort & Seawater Spa, featuring ocean-view rooms, suites, and cottages, plus a world-class seawater spa. Daunt's Albatross is a casually cool, family-run boutique motel featuring a saltwater pool and daily dining at the Bird on the Roof café across the street. Boutique hotels like Hero Beach Club and Breakers, present varying takes on the new Montauk, while The Surf Lodge offers a boho-chic waterfront retreat known for live music, wellness programming, and an irresistible summer energy. Wherever you decide to stay, you’ll be close to beaches, parks, and shopping.
8 pm: Dinner at South Edison
There are plenty of options for restaurants in Montauk. To start the weekend on a sophisticated note, head just one block south of town to South Edison, which serves fresh seafood and farm-to-table cuisine in an upscale-casual dining room with sleek city-meets-beach décor.
SATURDAY
7 am: Go fishing! (optional)
Many who come out east are here for one thing: Montauk fishing! Whether you’ve booked a private fishing charter or want to try your hand at reeling in a few bluefish, bass, or fluke out on the open waters, this town has you covered. If you’re in the latter category, head to the docks on Montauk Harbor and look for half-day trips with a reputable operator like Viking Fleet (which also offers whale watching cruises), Ebb Tide, or Miss Montauk II.
9 am: Grab breakfast at Montauk Bake Shoppe
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If you’ve missed the boat, so to speak, head to Montauk Bake Shoppe, one of the best breakfast spots in town, for a mix of savory and sweet options to go. Grab their famous fried jelly croissant, an egg sandwich on a fresh-baked bagel, or try a “cruffin,” a mash-up of a croissant and a muffin that locals swear by. Traveling with kids? There are buttermilk pancakes and French toast on offer as well. This place is a classic, too; the menu notes they’ve been “Serving Montauk for over 50 years" and have introduced a second location in East Hampton, open year-round. For a sit-down breakfast, Bird on the Roof is one of Montauk's most-raved-about spots, beloved for blueberry pancakes and a soft scramble toast with avocado and burrata.
10:30 am: Visit the Montauk Lighthouse
Photo by Lenny Catalanotto, Courtesy of Discover Long Island
One of the most picturesque places in all of New York State is Montauk Point, the home of Montauk Lighthouse (pictured), completed in 1796 after authorization from President George Washington. Today, the beautiful 110-foot tower houses a museum about its rich history (admission is $15 for adults, $10 for seniors and $5 for children 12 and under; parking is $8 from 8am-4pm), while the grounds around it encompass a state park, scenic bluffs, and of course, beaches. If you’re visiting from November-April, be sure to take a stroll along the shore–you may even get to see seals sunning on the rocks!
1 pm: Grab lunch at Inlet Seafood Restaurant
Credit: Bonnie Brady
Before heading back from the Point, have lunch at Inlet Seafood Restaurant, a stunner on Lake Montauk known for its sushi (pictured), lobster rolls, burgers, and more. Owned and run by six commercial fishermen from the area, this is a homegrown gem. Try to score a table on the second level, which offers tranquil views of the surrounding waters. (If you can’t make it for lunch, a sunset dinner here is also spectacular.)
2:30 pm: Spend some time on the sand
Credit: Marta Zielinska
Drive back to town, ditch the car, and spend the rest of the afternoon on one of Montauk’s famous beaches. Kirk Park Beach is a public beach with lifeguards, restrooms, and a usually pleasant surf that’s great for playing in the waves. It can get crowded in summer but hey, Montauk isn’t as sleepy as it used to be. For a more secluded experience, Hither Hills State Park offers a beautiful ocean beach with campsites, hiking and nature trails, and the unique "walking dunes" of Napeague Harbor. History buffs and outdoor adventurers should also consider Shadmoor State Park (pictured) or the Camp Hero State Park, a 415-acre park with dramatic Atlantic bluffs and pristine maritime forests, world-class surf fishing (permit required), extensive hiking and biking trails, and a fascinating former WWII military installation registered as a National Historic Site.
5 pm: Grab a beer at Montauk Brewing Company
Credit: @montaukbrewco on Instagram
A short walk from Kirk Park Beach is the charming tasting room for Montauk Brewing Co., the craft brewer whose beers reference their location, in name and in flavor. The company makes a crisp pilsner and a light summer ale that perfectly complement a day spent on the beach, while their IPAs and fruit-tinged specials are perfect as a seaside aperitif. They're also gaining national recognition for their non-alcoholic lineup. For families whose kids’ boundless energy prevails over the beach, wind down with a game of mini-golf at Puff ‘N’ Putt (open seasonally on weekends starting in mid-May).
6 pm: Choose your sunset spot
Decisions, decisions. In the mood for a sunset cocktail at Navy Beach (pictured)? Head to Duryea’s for a glass of rosé and lobster on the docks for a more casual night out (or with kids). Trust the locals when they say you'll love the sunset views and vibes at The Montauket. Or just take a stroll on the beach. There’s no incorrect way to do sunset in Montauk.
8 pm: Grab dinner at Gigi’s Montauk
Still hungry and want to tap into Montauk’s more glamorous side? Head to Gurney’s Montauk Resort for dinner at Gigi's, the resort's premier dining destination offering spectacular ocean views and a coastal fine-dining menu built for sharing. You’ll get a true taste of Long Island with a new-American menu that features impressive seafood towers, delicate crudos, locally-sourced fish, premium steaks, handmade pasta, and decadent house-made desserts.
SUNDAY
8 am: Grab a quintessential New York breakfast
Head to Goldberg's Bagels for fresh-baked bagels, breakfast sandwiches, and "flats," a flattened bagel with more surface area for cream cheese. Don't let the lines scare you off in summer, they move quick!
9 am: Spend the morning surfing or golfing
Surf’s up! Take a surfing lesson with one of the many teachers who offer 1.5-hour private or group lessons, such as Coreyswave. They welcome first-timers but be sure and reserve in advance during busy summer weekends. Not up for surfing? If a round of golf appeals, hit the greens at Montauk Downs State Park Golf Course (pictured), a public 18-hole, par-72 course dating to 1927. Redesigned by famed golf course architect Robert Trent Jones Jr. in 1968, Montauk Downs is open year-round and features a driving range, clubhouse, and more.
12 pm: Time for more seafood!
If you’re looking to squeeze in a little more seafood before you hit the road, try 668 The Gig Shack back on Montauk’s main drag. The menu has something for everyone with lobster rolls, blackened fish tacos, burgers, and even a grilled chicken croissantwich. There's also a kids menu.
1 pm: Pick up souvenirs
Nearby is Montauk’s vibrant downtown featuring a great collection of shops where you can pick up souvenirs. Homeport offers a selection of clothing, accessories, and local finds and Montauk Clothing Company has all things coastal apparel and Montauk-themed gear. If you’ve got a sweet tooth, the nostalgic Candied Anchor has gourmet candy, chocolates, and desserts.
3 pm: Stop for ice cream
As you leave magical Montauk, give yourself a treat at the cash-only John’s Drive-In, a local institution since 1967 that makes its own ice cream on-premises, including soft serve! Grab a cone of your favorite flavor topped with rainbow sprinkles and hit the road back to reality, but with amazing memories of your Montauk trip.
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