NEWSLETTER
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 and impressive collection of modernist seaside architecture.
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, which starts at the Pines and ends in Cherry Grove. Photo Courtesy of Discover Long Island.
Updated 04/29/2025
FRIDAY
1 pm: Hop on the ferry
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 so be sure to bring your best walking shoes! To reach either the Pines or Cherry Grove, 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). The boat ride drops you off in the “downtown” part of each village, where you’ll find most of the restaurants, shops, and nightlife. Check MTA Away for any special beach and summer getaway packages.
2 pm: Head to the beach
Credit: @kellyom_pilates_and_wellness on Instagram
As soon as you arrive, hit the beach to soak up the sun and surf! The Fire Island National Seashore is a wondrous stretch of nature, and both the Pines and Cherry Grove 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.
4 pm: Go dancing at the Blue Whale
It’s not a trip to the Pines without a stop at the legendary Low Tea at The Blue Whale, a Fire Island institution known as the home of the original “Tea Dance,” started in 1966. Enjoy the biggest happy hour in town with stunning harbor views, cocktails, and coastal fare.
7 pm: Fuel up for the night at Pines Pizza
Nothing hits the spot quite like a slice of pizza. Take a two minute walk to this pizza mainstay with a deck overlooking Fire Island Boulevard for a perfectly crisp, thin crust slice with all your favorite toppings, salads, and more.
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
9 am: Grab breakfast at Canteen
Start your morning with breakfast on the boardwalk at Canteen in The Pines. Perched harborside, grab an egg sandwich and a cup of coffee and watch the boats and ferries roll in as you get ready for another day of adventure.
11 am: Explore the Sunken Forest
Nearby, take a short ferry ride to check out a natural phenomenon that’s unique to Fire Island— The Sunken Forest. 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).
3 pm: It’s time for Cherry Grove
Photo courtesy of Discover Long Island
Next, climb aboard the ferry to Cherry Grove, where you can wander along the boardwalk and explore local shops. Be sure to stop by Sweet Licks Ice Cream to cool off with a treat!
6 pm: Dinner with a view
Photo courtesy of Discover Long Island
Up the wow factor at dinnertime as you settle in at Sand Castle on the Ocean (pictured) serving up delectable surf and turf with amazing Atlantic Ocean views or Top of the Bay, where you’ll find unique twists on classic dishes served alongside stunning views of the sunset over Great South Bay. Cherry Grove Pizza is the spot for delicious, giant New York–style pies and slices, plus a variety of pasta dishes.
9 pm: Dance the night away at Ice Palace
For a night of fun, visit the longest continually-running LGBTQ+ nightclub in the world, Ice Palace, which hosts drag shows, dance parties and other nightly events.
SUNDAY
10 am: Take a beach stroll
Photo courtesy of Discover Long Island
Start your last day on Fire Island with a relaxing walk on the beach and soak in some final moments in the sun and sand.
12 pm: Enjoy lunch with a view
Photo courtesy of Discover Long Island
Grab a burger or a modern seafood dish and take in the scenery on the outdoor seating deck nestled on the glistening Great South Bay at Island Breeze or toast to your excellent weekend with brunch at Cherry’s on the Bay (pictured), where you can watch the ferry arrive 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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This article was originally published 04/19/2019.