Living on an island means being surrounded by beach towns.
Lounging in the sand, dining on the water, strolling along the boardwalk, and being stuck in oceanfront traffic are all part of the Long Island beachgoer’s rite of passage.
Here's a guide instructing those seeking sand and sun on how to get to some at Long Island's beach towns. So, grab a towel and some sunblock, and follow the sound of the waves.
Getting there: As a true beach town should be, Fire Island is best accessed by boat. Hop a ferry out of Bay Shore, Sayville or Patchogue and enjoy a roughly half-hour cruise across the Great South Bay. With the island’s many car-free communities, arriving by sea is highly recommended. Water taxis are available but can be costly. Is Uber Boat available yet?
Dining scene: If captaining your own vessel to grab dinner or lunch at a bayfront restaurant, dock at one of the island's marinas. Enjoy some seafood or American cuisine at Maguire’s Bayfront Restaurant in Ocean Beach (1 Bungalow Lane) while taking in the island’s most picturesque views of the sunset. Grab a drink at fixtures like C.J.’s Restaurant and Bar (479 Bay Ave.) — a first stop off the Ocean Beach ferry that’s home to lobster specials and the popular rocket fuel tropical drink — and Flynn’s (1 Cayuga St.) — which offers happy hour and live music during the day and a nightclub vibe after dark, as well as waterside dining and even dining *on* the water with their dinner cruise.
Take the kids for some of the island’s best pancakes, French toast and egg sandwiches at Rachel’s Bakery and Restaurant (325 Bay Walk, Ocean Beach), or simply stop in for a cup of coffee and comfort foods like the famed crumb cake at the all-day eatery. For upscale dining, there are options like Top of the Bay in Cherry Grove (159 Dock Walk), The Hideaway in Ocean Beach (785 Evergreen Walk), and the Pines Bistro in Fire Island Pines (36 Fire Island Blvd.).
Exploring nature: The 32-mile long island is situated between the Great South Bay and Atlantic Ocean and bookended by Robert Moses State Park and Smith Point County Park. In between are 101 miles of coastline with beaches stretching from Kismet to Ho Hum Beach and beyond. Get out of the sun for a bit by taking a stroll around the 1.5-mile boardwalk of the Sunken Forest in Sailors Haven, a rare maritime holly forest sunken behind dunes near the island’s center.
Getting active: Fire Island is a haven for boating, surfing, fishing and other outdoor activities. Rent a bike on the island and take a ride down multiple trails, but be sure to let some air out of the tires for a smoother ride in the sand. Get a bird’s-eye view of the island by going parasailing in Ocean Beach. Go camping at Watch Hill. Take a hike through nature trails that stretch from two to five miles long. Or simply walk around the communities.
Getting there: Directions to Montauk are short and simple: head East. The commute there isn't always quite as easy, particularly during peak season when in gridlock with fellow beachgoers traveling to Long Island's easternmost point. The drive on Sunrise Highway eventually will merge into one lane, weaving through areas in the Hamptons that are home to some of the country's most renowned beaches. If you'd rather not be behind the wheel, hop on the Hampton Jitney, a bus service with connections at MacArthur Airport via reservation, or take the Long Island Rail Road, with a train from Patchogue to Montauk taking roughly an hour and 45 minutes.
Dining scene: Breakfast in Montauk starts with a difficult decision: a stack of pancakes at Anthony's Pancake House or John's Pancake House? The answer: whichever of the longtime and typically crowded establishments has a table available first. Other mainstay eateries include Harvest on Fort Pond for Italian, Gosman's Dock for seafood, Shagwong Tavern for clams, John's Drive-In for ice cream, and The Lobster Roll (aka LUNCH) for, well, lobster rolls.
Montauk's ever-expanding menu continues to evolve with a growing list of popular eateries like Navy Beach, where diners can eat on a private beach overlooking Fort Pond Bay with their toes in the sand; Joni's Kitchen, with creative breakfast offerings, acai bowls, salads, wraps, and healthy alternatives; and The Inlet Seafood Restaurant, for sushi and views of the Long Island Sound. There's also The Crow's Nest, Duryea's Lobster Deck & Seafood Market, The Surf Lodge and many more. Wash it all down at Montauk Brewing Co.
Exploring nature: Nearly an island in itself with water to its north, south and east, Montauk offers natural beaches and towering bluffs. There are plenty to choose from — some sandy, some rocky — including favorites like Ditch Plains, Gin Beach and Kirk Park Beach. Reserve a beach cottage at Gurney's Resort & Seawater Spa and consider their Beach Club, which includes king-size daybeds on a private beach. Or simply walk the shorelines at Montauk Point State Park Beach to take in views of the Montauk Lighthouse as ocean waves crash into boulders along Long Island's endpoint. Hike or bike the various nature trails along cliffs and overlooks at various parks, including Camp Hero State Park, Shadmoor State Park and Hither Hills State Park, which features Walking Dunes.
Getting active: See Long Island from above with Montauk Parasail. Hit the links at Montauk Downs State Park Golf Course, an 18-hole, par-72 public course. Take surf lessons or learn to stand-up paddleboard at one of many water activity locations like CoreysWave. Rent a bike at Montauk Cycle Company. Go horseback riding at Deep Hollow Ranch. Or just get a boat, kayak, canoe or Jet Ski at various rental locations and set sail.
Getting there: Nestled between the Hamptons and the North Fork, but surrounded by water, Shelter Island is most readily reached by sea. For those traveling from the south, board the South Ferry in North Haven. Visiting from the north, take the North Ferry from Greenport. In either direction, the relaxing ride along the Peconic River takes about 10 minutes. Helicopters and boat-cars are also options, but we're assuming the ferry is more practical for most. The ferry stations can be reached by car or the Long Island Rail Road. At both, boats run from about 5 a.m., leaving every 10-20 minutes, until 11:45 p.m.
Dining scene: Grabbing grub is convenient as there are several eateries along North Ferry Road. Early arrivers can enjoy a classic breakfast of omelets and French toast at The Islander on North Ferry Road. After a few hours of sightseeing, pick up a Tex-Mex lunch to-go at Maria's Kitchen. Gooey cheese quesadillas and grilled chicken salads are a good option for kids and even adults with not-so-adventurous taste buds. An upscale seafood-centric brunch or lunch can be had at Vine Street Cafe. Complement your grilled tile or Moules-frites with a glass — or few — from their deep selection of wines. Looking for a more familiar bite, or something the kids won't ask, "What's that?" swing by the recently-opened Shelter Island Slice to grab a slice of pizza.
Wrap up the day trip with dinner at 18 Bay. Keep your eyes peeled while traveling along North Ferry Road as this restaurant is set in a Victorian-era house. Inside, though, you'll be roused by the menu of fine Italian meals and local fish. If you've saved on calories throughout the day, try the five-course pasta tasting feast. SALT Waterfront Bar & Grill offers everything from lobster rolls to gyros.
Exploring nature: Of course, as one would infer from the town's name, there is plenty of coastline. Enjoy kayaking and kiteboarding at Shell Beach on the island's southern peninsula. Enjoy the sand and ambiance of Crescent Beach, located on the north and within walking distance of Sunset Beach Hotel and a few eateries. Enjoy bucolic views along hiking trails of up to 11 miles in the Mashamock Preserve, a 2,000-acre wildlife sanctuary. A visit to the Sylvester Manor Educational Farm is ideal for kids as it offers a quick lesson in agriculture and local history, along with archaeological sites and homegrown produce.
Getting active: Stop by Taylor's Island for some afternoon kayaking. Visitors often marvel at the serene scenery while paddling along the Coecle's Harbor Marine Water Trail. Kayaks can be rented and, for those inexperienced or uncomfortable paddling on their own, tours can be scheduled. The Shelter Island Country Club features a public nine-hole golf course that spans more than 2,500 yards with views of the Peconic Bay.
Getting there: Drive or ride, take your pick. The resort-like city is an isthmus connected to the mainland by bridges on its east and west ends. With that, area is easily accessible by land — traffic notwithstanding. Coming from western Long Island or New York City, head south past Far Rockaway and take the Atlantic Beach Bridge. From the east, Meadowbrook State Parkway connects to Loop Parkway, which carries a motorist straight into Point Lookout. The Long Island Rail Road is an option for those wanting to skip the highways and parking expenses, with the Long Beach station toward the center of the city. The LIRR offers a "Long Beach Package" that includes roundtrip train tickets, a coupon for the 24-hour Long Beach Bus and discounted admission to a beach.
Dining scene: Get breakfast or lunch at Lido's Kosher Deli. Try their Delicatessen omelet with pastrami, corned beef and salami, or keep it simple with a brisket sandwich. Head over to Brixx & Barley for a relaxing lunch and explore their something-for-everyone style menu. Get started with the tuna tartare or braised short rib tacos, then consider the lobster tortellini. There also is a vegan menu, and a variety of burgers and familiar dishes for kids.
If there's still room after lunch, hit Swingbelly's. The appropriately-named BBQ joint will send diners home full, what with its burnt ends chili nachos, pulled pork-stuffed jalapeños, Buffalo mac & cheese, grilled shrimp tacos and all the traditional barbecue dishes one would expect. Try Lost at Sea for seafood, Lost & Found for new American, and Gino's for a slice. The dining list also includes LB Social, Roc & Olive and JJ Coopers. The kids will love Dough Hut, offering specialty doughnuts, and Waffle Cabin, for signature Belgian waffles to go.
Exploring nature: The beaches, duh! Ocean Beach Park has a four-mile beachfront and a lengthy boardwalk, making it a popular spot for visitors. It's a good location to enjoy an afternoon swimming, surfing or playing beach volleyball. Nearby, there are fishing piers, playgrounds and eateries. To the east are Lido Beach and Point Lookout, which offers white sand and views across at Jones Bay. Visit the Lido Beach Passive Nature Preserve, a restored tidal wetland. The 40-acre site is home to several indigenous plants and a variety of vegetation and marine life. Settle in for a few minutes to do some bird watching and enjoy the views of the inland waterways. For those who drove, the Marine Nature Study Area might be worth a four-mile drive to Oceanside. The 52-acre preserve has tanks with specimens of marine life from the area along with plenty of educational material.
Getting active: Skudin Surf offers water sports including windsurfing and paddleboarding, along with surfing lessons for kids. Unwind during sunset by cruising along Reynolds Channel in a private yacht chartered through Long Beach Charter Cruises. A two-hour ride costs $495.
Getting there: Once you start seeing vineyards, you're close. Take the Long Island Expressway as far as it goes, wind your way toward Main Road, take it to the near end of the North Fork and escape into the tranquility of this quaint village. Along the way you'll pass farmlands and wineries, all without the heavy congestion that Hamptons traffic brings to its sister Fork. The Long Island Rail Road also stops in Greenport, with a train ride from Ronkonkoma taking approximately an hour and a half. Near the train station there's a Hampton Jitney drop-off point, as well as ferry service to and from Shelter Island.
Dining scene: Let's just say that Front Street and Main Road have enough dining options to satisfy the most undecided of diners and their palettes. The village's burgeoning dining scene boasts an eclectic mix of menus that perfectly complement the area's long-standing mayor of eateries: Claudio's.
For upscale seafood and new American fare, head to noah's. For breakfast and lunch made with local produce, try Bruce & Son, which on Saturday's hosts the popular PAWPAW pop-up serving ingredients strictly of Long Island flavor. For a "classic diner with a twist," grab a seat at Crazy Beans. The list goes on with The Freaky Oyster, First and South, Porto Bello, 1943 Pizza Bar, Billy's by the Bay, Industry Standard Bar, Olive Branch Restaurant & Bar, KonTiki, PORT Waterfront Bar & Grill, and so on. Depending on your preference of post-meal beverage, head to either North Fork Roasting Co. for a cup of coffee prepped by Artisan roasters; or to Brix & Rye, a speakeasy with classic cocktails; or to Greenport Harbor Brewing Company, a brewery and tasting room situated in a mid-1800's firehouse.
Exploring nature: While the dining is in the heart of town, the beaches in the area are a short drive, including Town Beach and Truman's Beach. Inlet Pond County Park features wooded trails that lead to a freshwater pond. Set up a tent and spend the night at McCann's Campground.
Getting active: Arrange for bicycle delivery to your house, hotel, marina or train station through Dan's Bike Rental. Hop onboard a sailboat, lounge in a beanbag chair and sip wine during a chartered trip with Layla Sailing. Throw on a pair of skates and head to George D. Costello Sr. Memorial Skating Rink. And, of course, no visit to Greenport is complete until stopping by Mitchell Park to take a ride on the antique carousel.