Your vacation guide to Fire Island's Cherry Grove and The Pines

Fire Island Pines

This LGBTQ-centric community is also 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. 

Fire Island Pines, architecture

The living room of a modernist house built in the 1960s in the Pines, where there is an unparalleled collection of modernist beach architecture by the likes Horace Gifford, Andrew Geller and Don Page. Take a walking tour of the Pines’ Modernist masterpieces. Go to pinesmodern.org for a map of distinguished homes including the TV house at 142 Ocean Walk and an Earl Combs octagon at 30 Fire Island Blvd. 

Fire Island Pines, 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.

Fire Island Pines, where to eat, drink and dance

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. 

Pictured: Partyers crowd the dance floor earlier this summer, during Low Tea at the Blue Whale.

Fire Island Pines, where to play

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. 

Pictured: Visitors relax earlier this summer at the Pavilion pool in the Fire Island Pines. 

Fire Island Pines, where to shop

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. 

Pictured: Dan Ofori tends to the displays at Tola.

Cherry Grove

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

Cherry Grove, 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. 

Pictured: The Venetian-inspired Belvedere Guest House for Men.

Cherry Grove, where to eat, drink and party

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 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. 

Pictured: Bartenders mix drinks at the Sand Castle.

Cherry Grove, where to eat, explore and shop

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 house-made granola.

Cherry Grove, where to play

Nightlife abounds. Cherry’s on the Bay (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.

Pictured: Guests take in a poolside drag show at the Ice Palace in Cherry Grove during late July 2018.

Getting there

To get to Cherry Grove or the Pines take the Sayville Ferry (sayvilleferry.com) on River Road in Sayville. Park in the nearby lot ($9/day Monday to Thursday; $16/day Friday through Sunday; call lot at 631-589-7548) or take the LIRR to Sayville and then a taxi to the terminal. Round-trip fares on the ferry are $18 for adults, $8.50 for kids and $5 for dogs. Credit cards are accepted in the Cherry Grove office. Passengers are limited to two pieces of luggage, one large suitcase or a small cart. Beyond that, wagons, loaded strollers and hand trucks are $8 on ferries, other large items between $2 and $8.