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48 Hours in Cherry Grove and the Fire Island Pines, NY

Cherry Grove and The Pines Have Long Been A Cherished Getaway For The LGBTQ Community

by Our Editors
48 Hours in Cherry Grove and the Fire Island Pines NY

from families and couples to LGBTQ vacationers, who gravitate toward Cherry Grove and the Fire Island Pines, communities that have been gay-friendly since before Stonewall.

Photo: I Love NY

Located east of New York City, just off the southern edge of Long Island, 31-mile-long Fire Island is home to some of the most spectacular, pristine beaches in the United States.

Its proximity to NYC and the laid-back vibe have made Fire Island a favorite for all types of visitors—from families and couples to LGBTQ vacationers, who gravitate toward Cherry Grove and the Fire Island Pines, communities that have been gay-friendly since before Stonewall. These two charming villages make for a perfect summer weekend retreat. Just follow the itinerary below.

FRIDAY
4 pm: Hop on the ferry

CREDIT: @FIPINES ON INSTAGRAM

CREDIT: @FIPINES ON INSTAGRAM

Kick off your weekend in Fire Island with a serene ferry ride through the Great South Bay—and you’ll have to; the boat is the only way to get here since this section of Fire Island is car-free. To reach both Cherry Grove and the Fire Island Pines, you’ll want to catch the Sayville Ferry, just a quick shuttle ride from the Sayville LIRR station (buses will be waiting when your train gets in). Check MTA Away for any special beach and summer getaway packages.

7 pm: Grab dinner at Pines Bistro or Top of the Bay

CREDIT: @TOPOFTHEBAYBISTRO_ ON INSTAGRAM

Top of the Bay (CREDIT: @TOPOFTHEBAYBISTRO_ ON INSTAGRAM)

Whether you’re staying in the Grove or the Pines, the 20-minute boat ride drops you off in the “downtown” part of each village, where you’ll find most of the restaurants, shops, and nightlife. For your first night, fuel up at the Pines Bistro and Martini Bar, serving seasonally inspired fare in the Pines, or Top of the Bay (pictured) in Cherry Grove, where you’ll find unique twists on classic dishes served alongside stunning views of the sunset. Both locations can get busy during the peak of summer, so call ahead for reservations.

9 pm: Hit the club

After dinner, get a sample of the Pines’ world-famous nightlife. Sip N Twirl on Fire Island Boulevard is the biggest club here, and it offers the chance to socialize, drink, and dance into the early hours. Or check out the nearby Pavilion, a sprawling, architecturally stunning complex with indoor and outdoor bars, terraces, and a dance floor. Though it’s a popular daytime hangout, it’s also open late into the night.

SATURDAY
10 am: Grab breakfast at Rachel’s

Hop on a bike and head over to Rachel’s Restaurant & Bakery in Ocean Beach. This Fire Island staple, founded in 1975, will fuel you for the day, whether you choose fresh pastries or a savory brunch.

12 pm: Tour a Lighthouse

Fire Island Light House

Fire Island Light

Climb the 182 steps of the Fire Island Lighthouse and enjoy a tower tour ($10 adults, $5 seniors, $5 children) Revel in the magnificent panoramic views of the ocean, Fire Island, the bays, Long Island to the north and on a clear day the skyline of New York City. After soaking in the scenery, view two floors of interactive exhibits in the Keeper’s Quarters.

1 pm: Head to the beach

CREDIT: @KELLYOM_PILATES_AND_WELLNESS ON INSTAGRAM

CREDIT: @KELLYOM_PILATES_AND_WELLNESS ON INSTAGRAM

The Fire Island National Seashore is a wondrous stretch of nature, and Cherry Grove and the Pines are right in the middle of it. You can spend the day sunning yourself, frolicking in the surf, and taking photos that will make your friends and family members Insta-jealous. Keep in mind that some of the beaches are unguarded, so be careful and heed surf advisories.

3 pm: Explore the Sunken Forest

The Sunken Forest

The Sunken Forest

Just to the west of Cherry Grove, you’ll find a breathtaking natural phenomenon: The Sunken Forest (pictured). This collection of holly trees gets its name thanks to an optical illusion—the high dunes that separate it from the nearby beach tower over the forest floor, giving you the sense you’re below sea level as you stroll through on the boardwalk (technically you are not).

7 pm: Plan your evening

Cherry Grove

Cherry Grove

While the Pines are perfect for high-octane partying, Cherry Grove offers a more relaxed nightlife. Have dinner at Cherry Grove Pizza, which serves delicious, giant New York–style pies and slices, plus a variety of pasta dishes. Up for an adults-only night out? Visit the Ice Palace, which hosts drag shows, dance parties and nightly events.

SUNDAY
10:30 am: Explore the local architecture

Along with its long-running status as a haven for the LGBTQ community, especially its artists, actors, and writers, Fire Island continues to attract architecture and design buffs. In fact, Cherry Grove and the Pines offer an impressive collection of modernist seaside architecture. Pines Modern offers an interactive map with details about architects and standout projects to seek out on a morning stroll.

12 pm: Enjoy lunch with a view

CREDIT: @ERINCOLTON ON INSTAGRAM

CREDIT: @ERINCOLTON ON INSTAGRAM

Sit back and enjoy a delightful lunch with a view at Island Breeze in Cherry Grove. Grab a burger or a modern seafood dish. Take in the scenery on their outdoor seating deck right on the glistening Great South Bay (a perfect spot to view the sunset if you decide to go for dinner).

1:30 pm: Hit the shops

Don’t forget to bring home some gifts and souvenirs to remember your weekend memories. Search the Ocean Beach boutiques for the perfect item, then stop by a few of the Pines’ finest shops—TOLA and General Store, both featuring upscale gifts and chic clothing.

3 pm: One last hurrah

Cherry's on the Bay

Cherry’s on the Bay

Toast to your excellent weekend at Cherry’s (pictured) in Cherry Grove, an outdoor bar known for its fruity mixed drinks. You can watch the ferry arrive from Cherry’s, so you’ll know exactly when it’s time to set sail back to “the mainland.”

HOTELS & RENTALS

Grove Hotel
Dune Point
The Palms Hotel
The Madison Fire Island Pines

GETTING THERE

By Car (travel time to Sayville Ferry):
From New York City: 1 hour 30 minutes
From Philadelphia: 3 hours
From Albany: 3 hours 30 minutes
From Boston: 4 hours
From Syracuse: 5 hours 10 minutes
From Montreal: 7 hours
From Buffalo: 7 hours 15 minutes
Note: Drive times can vary greatly depending on traffic in summer months; allow extra time if you’re traveling during peak season.

By Train:
Take Long Island Railroad to Sayville Station, then take a taxi or shuttle bus to the Sayville Ferry.

By Plane:
Fire Island is easily accessed from all New York City airports. The Long Island MacArthur Airport, with service from American, Frontier, and Southwest Airlines, is about 20 minutes away.

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