Aboard a Fire Island ferry to Ocean Beach, Brian Shea,...

Aboard a Fire Island ferry to Ocean Beach, Brian Shea, of Larchmont in Westchester County, takes a selfie with his family, clockwise from left, Kyle, Margaret, and Trevor.  Credit: Daniel Goodrich

Fire Island has been inhabited by pirates, whalers and the Coast Guard. Today, its population is just as diverse. Distinct but overlapping communities welcome young singles, families, moguls and regular Joes. All vacationers agree that the absence of cars and proximity to the water are the prime attractions. Then there are restaurants, clubs, shops, historical sites and natural wonders galore. Here is a guide to vacationing in 7 of the island's most popular communities.

KISMET For nature lovers  

The westernmost community on Fire Island is both a nature lover’s paradise and a party person’s dream.

People walk along the beach at Kismet on Fire Island. 

People walk along the beach at Kismet on Fire Island.  Credit: Marisol Diaz-Gordon

WHERE TO STAY Share houses abound in Kismet, where friendly partying takes place on beach cottage deck after beach cottage deck. Margarita Villas (631-583-5325; margaritavillasllc.com), a group of formerly derelict apartments renovated by brothers Chris and Greg Pecoraro, is now the option in Kismet for daily, weekly and monthly room rentals. If your group is large (a family reunion, bachelorette party or birthday celebration) book the Margarita Villas’ Taj Mahal, a seven-bedroom, two-bath house that can sleep up to 26.

Surf's Out, a popular eatery in Kismet on Fire Island. 

Surf's Out, a popular eatery in Kismet on Fire Island.  Credit: Johnny Milano

WHERE TO EAT There are two choices in Kismet, the Inn and the Out. The Kismet Inn (631-583-5592; thekismetinn.swamponline.com) has been a community gathering place since 1953. Serving an old-fashioned and crowd-pleasing menu that includes everything from clams casino to chili dogs, it overlooks the bay and marina and is open seven days for lunch and dinner.

Surf’s Out (631-583-7400; surfsout.com) is the youngster, celebrating just over 10 years in business. In addition to old favorites like spaghetti and meatballs and linguine with clam sauce, it serves trendy items like kale and quinoa salad, along with a full sushi menu. The courtyard at The Out serves as a stage for live bands on Saturdays and some Sundays from 6 to 10 p.m. On Sundays, it hosts a $45 Shipwrecked Bottomless Brunch and DJ Party beginning at 11:30 a.m. so patrons can “dance under the sun.” If you’d like to take a swim, the Out offers more than 30 free lockers and two showers — bring your own lock and towel.

Visitors ride bikes along the walkways of Fire Island's Kismet community. 

Visitors ride bikes along the walkways of Fire Island's Kismet community.  Credit: Marisol Diaz-Gordon

WHAT TO DO Both Robert Moses State Park’s Field 5 and the Fire Island Lighthouse are within walking distance of Kismet. Day-trippers can park at Field 5 of Robert Moses State Park (631-687-4750, parks.ny.gov), enjoy the beach, and then stroll the boardwalk nature trail that leads from Field 5 to the iconic Fire Island Lighthouse (631-321-7028, fireislandlighthouse.com), with its black and white stripes. Climb the lighthouse’s 182 steps for a view of the 32-mile barrier island coastline. 

INSIDER'S TIP Buy flowers on the dock on Friday nights from full-time residents of Kismet, who are raising money to pay for the beach’s lifeguards.

SALTAIRE Quiet residential hamlet 

This small incorporated village is known as the most insular community on Fire Island, with no hotel rooms, very little shopping and only one restaurant, at the members-only Saltaire Yacht Club. That said, it is an extremely friendly place for those lucky enough to rent a house there, offering youth sports programs, a day camp, basketball courts and tennis for residents.

A ferry docks at Saltaire on Fire Island, and will...

A ferry docks at Saltaire on Fire Island, and will return to Bay Shore.  Credit: Johnny Milano

WHERE TO STAY If you want to stay in Saltaire, you’ll have to rent. Barrierbeachproperties.com offers some beautiful houses, with a two-week minimum. (They also specialize in Saltaire sales, if you fall in love with the place.) For shorter stays, check, airbnb.com.

Chelsey Rubin, left, and Roopa Unnikrishnan, both of Manhattan, dine...

Chelsey Rubin, left, and Roopa Unnikrishnan, both of Manhattan, dine on Labor Day barbeque at the Saltaire Yacht Club on Fire Island.  Credit: Marisol Diaz-Gordon

WHERE TO EAT AND DRINK The Village’s only restaurant is at the Saltaire Yacht Club (631-583-5117; saltaireyc.com), which is the village’s social hub. It’s open only to members and their guests, but renters are eligible to join, and depending on the length of your stay the membership fees (just under $2,000, which includes sailing and a $225 restaurant credit) might be worth the benefits. In addition to selling groceries, Saltaire Market (631-583-5522; saltairemarket.org) has a full takeout menu, everything from penne alla vodka to seafood paella as well as pizza by the pie and slice.

Patrick Busby, of Brooklyn, on the beach in Saltaire. 

Patrick Busby, of Brooklyn, on the beach in Saltaire.  Credit: Marisol Diaz-Gordon

WHAT TO DO The Saltaire Library (saltaire.org/library), located in the Village Hall, hosts frequent children’s story hours and other events, and brings in occasional adult authors for talks and readings. The Village also runs a daycamp for prekindergarten through sixth graders, with visits to the beach, nature study, drama, dance and more from 9 a.m. to noon on weekdays. The yacht club shows children’s movies once a week, open to the public.

INSIDER'S TIP Most of Saltaire is built on wetlands, so there are no concrete sidewalks, only wooden boardwalks, making it a particularly picturesque place for walking.

OCEAN BEACH Bustling, family friendly haven 

Ocean Beach is the most populous town on Fire Island with the biggest commercial district. Relatively unscathed by the hurricane of 1938, it has a good number of older houses, lending its streets old-fashioned charm.

The ferry dock in Ocean Beach on Fire Island. 

The ferry dock in Ocean Beach on Fire Island.  Credit: Linda Rosier

WHERE TO STAY Two big hotels compete for business from visitors to Ocean Beach. The Palms Hotel Fire Island (631-583-8870; palmshotelfireisland.com) is the luxury choice, offering rooms, suites and cottages with Egyptian cotton sheets and pillow-top mattresses. A courtyard has barbecues and outdoor showers for hotel guests. Bikes, umbrellas, wagons, and beach towels are available. Activities for kids include movies and arts and crafts. The hotel bar and restaurant, C.J.’s, claims to be the inventor of Fire Island’s unofficial cocktail, a vodka-tequila-rum concoction called the Rocket Fuel. Clegg’s Hotel (631-583-9292; cleggshotel.com), decorated in nautical navy and white to evoke a sailor’s rooming house, offers rooms with shared baths as well as suites with kitchenettes that can accommodate a family of four. A continental breakfast is included in the rate, and bicycles, beach chairs and umbrellas are also provided.

Mira and Fred Alomar, of the Bronx, have dinner by...

Mira and Fred Alomar, of the Bronx, have dinner by the bay at the Island Mermaid in Ocean Beach.  Credit: Linda Rosier

WHERE TO EAT For breakfast, stop in at Rachel’s Bakery (631-583-9552; rachelsfireisland.com) for a slice of Rachel’s famous crumb cake and a cappuccino. The recently renovated Ocean Beach institution also serves lunch and dinner in an airy dining room, and stays open until 4 a.m. to satisfy late-night cookie cravings. Along with a prime bay view, Island Mermaid (631-583-8088; islandmermaid.com) serves up creative versions of fish house classics. Crabcakes come with red onion tartar sauce. Pan-seared scallops are served with truffled creamed corn. For lobster rolls, seafood Cobb salad or the catch of the day, pull up a seat at the covered bar at Matthew’s Seafood at the east end of Ocean Beach (631-583-8016; matthewsseafood.com). Matthew’s also offers fresh fish, prepared food and groceries at its adjacent market, Matty’s. Houser's Bar (631-583-8900; housershotel.com), established in 1921 and the longest continuously running dining establishment on Fire Island, is home to good music and views of the Great South Bay, with a front-row seat to view a Long Island sunset. A snack, appetizer and food menu is available outside, and there's a full service bar with a pool table inside

A couple wallks along Brighton Lane in Ocean Beach, Aug...

A couple wallks along Brighton Lane in Ocean Beach, Aug 10, 2018. Credit: Linda Rosier

THINGS TO DO Ocean Beach’s main square is dotted with shops. Searching for the perfect Ocean Beach T-shirt? Try Kline’s (631-583-3333). Looking for decorative nautical décor? Browse through The Gallery (631-583-9724), often referred to as the General Store because of the sign above its front door. The Ice Castle Sweet Shoppe (631-583-0225) sells ice cream and fudge, along with shelves and shelves of candy. For beachy dresses and sterling silver and shell jewelry try Hanalei and Kula’s (516-220-1903; hanaleiandkulas.com), “where Hawaii meets Fire Island.”

INSIDER'S TIP Ocean Beach has a strict village code, with rules against eating on the beach. To avoid a summons, plan your dining carefully, fueling up at home or in a restaurant before hitting the sand.

OCEAN BAY PARK Party central 

Ocean Bay Park was originally conceived as a community for retired New York City police and firefighters. Today, it is a magnet for young people looking for a good time. There is also a strong sense of civic-mindedness coming from longtime homeowners, on display at the annual Community Fair, held this year on Aug.10 from noon to 3.

The Darcy family walks back to their home after a...

The Darcy family walks back to their home after a day at the beach in Ocean Bay Park.  Credit: Yvonne Albinowski

WHERE TO STAY If you haven’t purchased a share in a summer house, check into the Fire Island Hotel (631-583-8000; fireislandhotel.com), which occupies an old U.S. Coast Guard station, as do a few other commercial buildings in town. In addition to standard rooms, there are several two-bedroom detached cottages with kitchenettes, sleeping up to eight. Amenities include a pool, coffee bar, lounge and restaurant, and yoga on the beach.

Julia Knapp, left, of Bay Shore, and Michelle Waaland, of...

Julia Knapp, left, of Bay Shore, and Michelle Waaland, of Huntington, have their drinks outdoors at Flynn's in Ocean Bay Park.  Credit: Yvonne Albinowski

WHERE TO EAT AND DRINK Ocean Bay Park was developed around the Flynn family’s restaurant and casino on the Bay, which opened in 1937. Today, Flynn’s remains the center of Ocean Bay Park nightlife and a boisterous day time scene(631-583-5000; flynnsfireislandny.com). Sunday Funday features DJs and live music from 11 a.m. to 11:45 p.m. The Schooner Inn (631-583-9561; schoonerinnfireisland.com) opens at 8 a.m. for breakfast and doesn’t close until 4 a.m., when the DJ packs up. The bayfront complex has its own beach, a pizzeria, and two bars. The restaurant, with outdoor seating, serves standard Fire Island fare like fried calamari, Buffalo wings and linguine with clam sauce.

A steamed lobster platter is served at the Schooner Inn...

A steamed lobster platter is served at the Schooner Inn in Ocean Bay Park.  Credit: Yvonne Albinowski

WHAT TO DO The Schooner Inn rents bikes for exploring nearby communities. Hurricanes, at the Fire Island Hotel, has live music on Friday nights and on Saturday and Sunday afternoons.

INSIDER'S TIP Use caution when swimming, since there are no lifeguards on duty at the beach here, and riptides are famously powerful.

CHERRY GROVE Lively LGBTQ social scene   

Cherry Grove has a long history as a bohemian summer retreat, and it is still a favorite of artists, writers and actors. The LGBTQ community was welcome on Fire Island long before the watershed Stonewall uprising and made Cherry Grove (and the Fire Island Pines) its own. Vacationers of all stripes love the Grove for its colorful drag shows, lively nightlife and down-to-earth vibe. 

The Venetian-inspired Belvedere Guest House for Men, at Cherry Grove, may...

The Venetian-inspired Belvedere Guest House for Men, at Cherry Grove, may be the most architecturally distinctive lodging on Fire Island. Credit: Johnny Milano

WHERE TO STAY The Grove Hotel (631-597-6600, grovehotel.com), a town fixture since 1957, burned to the ground in 2015 but has risen from the ashes, with more spacious guest rooms and a familiar lineup of entertainment in its nightclub, the Ice Palace. The most architecturally distinctive lodging on Fire Island may be the Venetian-inspired Belvedere Guest House for Men (631-597-6448, belvederefireisland.com). Rooms in the palatial structure range from economy (four to a room with a shared bath) to luxury (water views, king bed, private bath). Clothing is optional. Dune Point (631-597-6261, dunepointfireisland.com), an oceanfront guesthouse, has cutely decorated rooms and suites with kitchenettes. 

Bartenders mix drinks at the Sand Castle restaurant in Cherry...

Bartenders mix drinks at the Sand Castle restaurant in Cherry Grove.  Credit: Johnny Milano

WHERE TO EAT AND DRINK Sand Castle (631-597-4174, fireislandsandcastle.com) serves contemporary cuisine, offering grain bowls and sandwiches like their signature lobster roll at lunch, interesting entrees like seared tuna tataki for dinner, and plenty of vegan and gluten-free options. Top of the Bay Bistro (631-597-6028, topofthebaycherrygrove.com) is a lovely New American spot, serving seared scallops with cauliflower puree and braised short ribs with pesto mashed potatoes, accompanied by spectacular sunsets. For breakfast and brunch, you can’t go wrong at Floyd’s (158 Bayview Walk, 631-597-3569), where all baking is done on premises and specialties include sticky buns, challah French toast and housemade granola.

Guests get a poolside drag show at the Ice Palace...

Guests get a poolside drag show at the Ice Palace in Cherry Grove.  Credit: Johnny Milano

WHAT TO DO Nightlife abounds. Cherry’s on the Bay (631-597-7859, cherrysonthebay.com) offers dinner and a show (“Dining with the Divas”) on Mondays; drag performer Hedda Lettuce doing stand-up, song and dance on Sundays and Tuesdays; and dancing with DJs on Fridays and Saturdays. The Island Breeze (631-597-9111, theislandbreeze.com) offers drag bingo on Thursdays at 5 p.m.

Visitors and residents mingle near the ferry terminal at Cherry...

Visitors and residents mingle near the ferry terminal at Cherry Grove.  Credit: Johnny Milano

A diverse, arty and historic community, it has been welcoming the LGBTQ community since the 1930s. The Cherry Grove Community House and Theater (artsprojectcg.org) has also been named to the National Register of Historic Places for, “the enormous role it played in shaping what gradually evolved into America’s First Gay and Lesbian Town.”

INSIDER'S TIP There are two annual drag contests in Cherry Grove: the Homecoming Queen show (artsprojectcg.org) during Memorial Day Weekend and the Miss Fire Island contest (grovehotel.com/miss-fire-island) the weekend after Labor Day. Both require tickets, which are available online in advance.

THE PINES History, architecture & gay culture 

This LGBTQ-centric community is the island’s most architecturally distinguished, with an unparalleled collection of modernist beach architecture by the likes Horace Gifford, Andrew Geller and Don Page. A little quieter and more low-key than Cherry Grove, it still offers plenty of opportunities for socializing by the sea, including high, middle and low tea dances (a Pines ritual since 1966) every day of the week in season. 

Houses line the beach at The Fire Island Pines. 

Houses line the beach at The Fire Island Pines.  Credit: Linda Rosier

WHERE TO STAY The Madison Fire Island Pines (631-597-6061, themadisonfi.com) is a bed-and-breakfast with bright and airy rooms, in photo, a pool and a pretty roof deck. The Hotel by ShareGurl (hotel.sharegurl.com) is a cleaned-up incarnation of the infamous Botel, with basic but affordable rooms for two to four guests. Go to sharegurl.com to rent Pines homes by the week.

Partyers crowd the dance floor during Low Tea at the Blue Whale...

Partyers crowd the dance floor during Low Tea at the Blue Whale in the Pines on Fire Island.  Credit: Linda Rosier

WHERE TO EAT AND DRINK Canteen (pinesfi.com/canteen) is a casual spot a few steps above Harbor Walk, great for a light breakfast, lunch or dinner with a side of people-watching. Pines Bistro & Martini Bar (631-597-6862, pinesfi.com/pinesbistro) is an upscale choice, an elegant Italian place located on the second floor of a Fire Island Boulevard building and above the crowds. Go to The Blue Whale (631-597-6500, pinesfi.com/bluewhale), order a Blue Whale (made with Blue Curaçao and vodka) and enjoy the full schedule of events that includes Saturday drag brunch and a cabaret. 

Visitors to the Pines use the pool at the Pavillion. 

Visitors to the Pines use the pool at the Pavillion.  Credit: Linda Rosier

WHAT TO DO Aside from sunning on the beach, clubbing is probably the most popular activity here. Pavilion (631-597-6500, pinesfi.com/pavilion), rebuilt by distinguished architectural firm HWKN after a catastrophic fire in 2011, is the community’s primary night (and day) spot, and includes indoor and outdoor bars, terraces, a dance floor, a gym and shops. The adjacent Sip-n-Twirl (631-597-3599, pinesfi.com/sipntwirl) has a large dance floor, breezy outdoor deck and no cover charge. Shop at Tola (631-597-5525, tolanewyork.com) for cool hostess gifts and fashion for men, women and children. General Store by Base (631-597-6500, baseworld.com) stocks a curated collection of books, candles, grooming products and other stuff people love to buy when they’re on vacation. 

INSIDER'S TIP If you love of a good party, visit the Pines during the two weekends when the community goes wild. During Invasion of the Pines (July Fourth weekend), scores of men invade the town in drag to commemorate the protest that took place after a resident in drag was refused service at a local bar in the 1970s. The Pines Party (pinesparty.com), July 26 to 28 this year, is a themed fundraiser for The Pines Foundation and the Stonewall Community Foundation, consisting of several pool- and beach-side bashes, with flowing booze and hours of dancing.

DAVIS PARK Boaters' paradise 

The easternmost community on Fire Island has just 350 homes, and over 200 boat slips in one of the Island’s largest marinas.

Beach homes line the shore at Davis Park on Fire...

Beach homes line the shore at Davis Park on Fire Island.  Credit: Marisol Diaz-Gordon

WHERE TO STAY With so few homes, rentals are scarce. Your best bet is to browse an aggregator website like tripping.com, which collects available rentals from vrbo, airbnb, homeaway, and other sites.

WHERE TO EAT AND DRINK Davis Park has just one restaurant, the Casino Café (631-597-6150; casinocafefireisland.com), which bills itself as “Fire Island’s only oceanfront restaurant.” Operating since June 6, 1945 (the day that Allied troops hit the beaches of Normandy), the Café serves dinner from 5 p.m., seven days a week. On the large and varied menu you’ll find everything from clams on the half shell to mahi tacos to chicken and waffles. The Casino Bar, rowdy sibling of the Café, features indoor and outdoor bars, dancing into the wee hours, and weeknight entertainment beginning at 9:30 including karaoke on Mondays and something called “dirty bingo” on Tuesdays.

Davis Park Marina on Fire Island. 

Davis Park Marina on Fire Island.  Credit: Marisol Diaz-Gordon

WHAT TO DO Leja Beach is lifeguarded throughout the season. If you have a boat, the Davis Park Marina (631-597-9090; davisparkmarina.com) might be the place to dock.

INSIDER'S TIP The Davis Park Medical Association (davispark.org) owns a house called Bedside Manor, which is rented to doctors and nurses in exchange for medical care provided to members during the summer. There are scheduled office hours, on-call availability, and a helipad for emergency evacuation capability. Membership is $60 per household and covers medical visits for everyone in the house. 

GETTING THERE Navigating the ferry system 

The ferry dock in Ocean Beach on Fire Island. 

The ferry dock in Ocean Beach on Fire Island.  Credit: Linda Rosier

Get to any of Fire Island’s car-free communities from one of three ferry terminals in Bay Shore, Sayville or Patchogue.

Fire Island Ferries is based on the south end of Maple Avenue in Bay Shore. It serves the communities of Kismet, Saltaire, Ocean Beach and Ocean Bay Park. Either drive and park in one of the pay parking lots south of Main Street or take the Long Island Rail Road to the Bay Shore station and either take a cab or walk south to the terminal. Round-trip Bay Shore ferry fares for 2019 are $21 round trip for adults, $11 round trip for kids, ages 2 to 11; $20 round trip for seniors, handicapped and military. Cash only. fireislandferries.com

Those going to Cherry Grove or Fire Island Pines take the Sayville Ferry based on River Road in Sayville. Sayville ferry riders can drive to nearby pay parking lots or take the LIRR to a cab to the terminal. Round-trip Sayville ferry fares are $18 for adults, $8.50 for kids and $5 for dogs; $16 for seniors and handicapped passengers. Credit cards accepted in the Cherry Grove office. sayvilleferry.com

Visitors to Davis Park take the Davis Park Ferry on Brightwood Street in Patchogue, where they can drive to a pay parking lot or take a train to a cab to the terminal. Round-trip Patchogue ferry fares are $17 for adults, $16 for seniors, $11 for kids and $6 for dogs. Cash only; checks accepted for multitrip options. davisparkferry.com