Fire Island Gay Travel
Find Fire Island gay hotels, house rentals, beaches, parties & events with wolfyy’s gay Pines guide.
The Gay Travel Experience: Fire Island Pines, New York
Stoic faces of New Yorkers relax into smiles on this wonderful barrier island. The Fire Island LGBT community becomes one, carrying on with cheerful activities under the sun.
A destination only reachable by boat, the secluded neighborhoods of Fire Island Pines and Cherry Grove are global gay travel must-sees.
The Fire Island Pines neighborhood holds significant history for the LGBT community. Originally a safe haven for gay men to express themselves freely, The Pines is held close to the hearts of many.
The Pines and Cherry Grove are the two neighborhoods that comprise the gay area of Fire Island. You absolutely must visit at least once!
Before getting into the details of this Fire Island Pines gay travel guide, I recommend you read the brief segment below about the precious history of these Fire Island gay communities.
Brief History on the Fire Island Gay Community
The LGBT history of Cherry Grove and Fire Island Pines dates back to the 1940’s.
When gay and lesbian members of society had no protections against discrimination based on sexual orientation, these hamlets on Fire Island were literal escapes from mainstream life.
Over time they have blossomed into today’s wonderful collective Fire Island gay community.
New Yorkers would leave their responsibilities behind, bound for a weekend getaway to a place where they could be themselves.
On this tiny island, they could live freely and show affection in public without repercussion. It was a place without rules, where LGBT people of all types could feel at ease.
Over the years, the gay communities of Fire Island Pines and Cherry Grove have continued to grow in popularity, even despite several destructive events such as powerful hurricanes and building fires.
The LGBT community has proved resilient in maintaining our sacred gay paradise outside of bustling New York City.
Fire Island Gay Hotels, Rentals & Where to Stay
Fire Island is a large, skinny barrier island off the southern coast of Long Island, New York. The Pines and Cherry Grove are two separate neighborhoods where the LGBT community stays.
Where in Fire Island Pines should you stay? I’ll help you decide. I’ll begin with what each neighborhood is like, then show you the trick to book a rental.
Staying in The Pines Vs Cherry Grove
The Pines is where most of the social action is, but Cherry Grove is not without its own flavor. They both are just about 100% gay neighborhoods, not to mention popular with many gay celebrities and influential New Yorkers.
The Fire Island Pines neighborhood will be a better choice if you prefer be in the center of the fun. In my opinion, first time Fire Island gay travelers should stay here.
Cherry Grove tends to have a slightly older population, but is truthfully just as popular. If you plan to attend the famous cherry Grove underwear party (more on this in the nightlife section), this neighborhood may be more convenient.
All in all, don’t stress too much about where to stay on Fire Island. There is no inferior area of this gay wonderland. But, try to reserve your spot as soon as possible before prices increase.
Fire Island Pines Rentals & Finding a House
If you’ve never booked a place to stay in Fire Island Pines, there are several important details you need to know.
How Rentals Work
Locals purchase what are essentially timeshare rentals from homeowners. Rotating groups of guys will occupy a house for one week of each summer month. These “shares” are frequently listed for re-rental. This is what you will look to reserve.
You will most likely reserve a single room within a shared house. Sometimes, even individual rooms are shared, usually among friends.
How to Book
You’ll want to join the Boys of Fire Island Facebook group used for reserving rooms in Fire Island Pines. Group approval is required, but as long as you don’t seem like a robot or have a blank profile, there should have no issue.
Create a post stating what type of accommodation you are looking for, as well as your budget. Keep in mind a single room with two twin beds generally runs about $600 USD per night.
Typically, guys will post a photo of themselves along with their solicitation for a place to rent in an effort to introduce themselves as a good candidate to share a residence with for the weekend.
Then, message people who have already posted availabilities. From here you can settle on details and payment, which usually requires some sort of deposit.
Planning Made Easier with wolfyy.
Add Your Email.
Fire Island Pines Rentals
Depending on how far in advance you are looking for your place to stay, VRBO might be a viable option. For last minute trips, you might find that VRBO options are expectedly slim. I would still do a search though. Here’s the best area for Fire Island Pines VRBO listings.
Some owners or those selling shares prefer VRBO’s simplicity and security. Do make sure to understand the conditions of each listing. Many have specific house rules, which will be the case no matter if you use VRBO or the Facebook groups.
Fire Island Gay Hotels
No matter where you are in The Pines or Cherry Grove, you’ll be surrounded by gay men. There is one gay hotel in The Pines and one in Cherry Grove, but there isn’t necessarily any type of Fire Island gay resort.
The Grove Hotel is a fantastic place to stay in Cherry Grove. It’s adjacent to the Ice Palace Nightclub, home to Fire Island’s best gay underwear party. You can also catch some hysterically funny drag shows here by the pool every weekend.
I advise against staying at the Fire Island Pines hotel located in the harbor. This hotel stays in business due to it’s proximity, but I’ve never met anyone who said they enjoyed staying here.
Sandy concrete floors, shared bathrooms between rooms and frequent power outages from blown fuses in hotel rooms are not what you want to experience while visiting a place as beautiful as The Pines. I did it once. Never again!
How to Get To Fire Island Pines: Directions from NYC
Getting to The Pines and Cherry Grove can definitely be confusing for first-time visitors. So read the following very carefully. I encourage you to bookmark this page for future use.
Departing from Penn Station in New York City via the Long Island Rail Road is most common. At the ticket machine in Penn Station, choose the special option of “getaways.” Proceed to the option of Fire Island Pines / Cherry Grove.
The tickets are about $40 per person round trip. A set of tickets for the train, shuttle bus and ferry will print, for both outbound and return journeys.
Sayville will be your destination train stop. Some trains running eastbound from New York City require a transfer at an intermediate station, so listen to the conductor’s instructions when he checks your ticket on the train.
If you are unsure which train, just ask someone near you. Most likely you’ll be following the crowd if traveling during a popular time.
Upon arrival at the Sayville LIRR train station, follow everyone toward the white mini-buses. These will shuttle you to the ferry in about seven minutes. Be prepare to cram in on busy summer times!
Ferry Service to Fire Island Pines
Once you’re at the ferry terminal, look for signs for either The Pines or Cherry Grove. There is a separate ferry for each neighborhood. The boat ride is roughly 20 minutes and quite enjoyable! These boats have open-air top seating decks where everyone gets comfortable in the summer sun.
It’s best to know your ferry departure time beforehand, so you can make sure your LIRR train arrival synchronizes well with your ferry departure. Here is the official Fire Island Sayville Ferry Service Schedule for Fire Island Pines. Note that Cherry Grove service is a separate schedule.
During busy times, especially in summer, ferries to Fire Island will typically depart shortly after a a train arrival, making the trip seamless. But during off-season, you should definitely check ahead to avoid waiting around unnecessarily.
Voila! You’ve made it to Fire Island. From the ferry drop-off point you will walk to your rental. Also, surprise! There are no cars on the island. The maze of boardwalks makes Fire Island even more majestic. It’s also one more reason to pack on the lighter side.
Fire Island Pines Gay Travel Experiences
Stroll the wide-open beaches, find a pool party and get ready for Tea! If your house does not have a pool, take advantage of the communal pool right in the harbor, completely free to use. You can grab a drink at the pool bar and relax after your journey.
Whether you’re here at the pool or anywhere else on Fire Island, you’ll definitely want to be strutting around in a fun, sexy swimwear look!
Strolling the winding pathways while embracing the wonderful local architecture is one of my favorite things to do in Fire Island. Neighborhoods here boast such beautiful vacation homes nestled in the woods.
To get oriented with the local gay scene, I’ll firstly mention the Pavilion. This complex a relatively new, mixed-use structure that hosts just about all the official Fire Island gay events such as Low & High Tea.
It houses all the restaurants in Fire Island Pines as well as the gym and public restrooms. The Pavilion is sort of like home base in The Pines.
Gay Pines Activities: Low Tea & High Tea
Low Tea at the Pavillion is a mainstay of gay social life in The Pines. Every day, especially Friday and Saturday, gay men fill the harbor to drink and be merry.
The gathering for Low Tea officially starts at 5:00 PM and continues until 8:00 PM. Usually by 6:30 or 7:00 PM, the deck is completely packed. Gay men take over, rain or shine!
As Low Tea winds down, High Tea is just beginning. As the time nears 8:00 PM, the crowd will pour to the adjacent pool deck, as well as toward the upper Pavilion deck.
High Tea is branded as an event called Sip n’ Twirl. As the sun sets, the music gets around the pool gets louder and the night transitions to dance mode!
You can always count on a live DJ entertaining patrons on both the pool deck and upstairs at Sip n’ Twirl. Just for your information, here is the official Sip n’ Twirl Web Page.
While you’re out enjoying Fire Island, keep fresh and prepared for anything with these on-the-go essentials. Everything from travel-sized bug spray to pocket combs to keep your hair on point.
The Fire Island Gay Beach: Where is it?
This is almost a trick question! The Fire Island gay beach is essentially all the beach area adjacent to Fire Island Pines and Cherry Grove.
These neighborhoods are the gay areas of Fire Island, so you’ll find LGBT beachgoers all along this stretch. Essentially, the entire waterfront is one giant gay beach.
Fire Island beach culture is quite relaxed. You’ll probably notice that these sandy shores are a little calmer than what you might imagine a typical gay beach to be like.
Fire Island Gay Beach Tips
Firstly, you’ll definitely need to pack cold drinks and snacks for your beach time. There are no commercial establishments on the waterfront. Remember that The Pines and Cherry Grove are largely residential communities. You won’t find any beach bars or even tents selling drinks.
Since the gay Pines community is so physically isolated, you will not even encounter any individuals selling drinks out of coolers. You’ll be completely on your own for this.
However, The Pines Pantry is not too far away should you need anything, but it comes at quite an elevated price.
The best thing about the beaches in Fire Island Pines is that they’re never crowded. There is always plenty of space to spread out, run around, or play beach games. If you prefer to travel light, I definitely recommend bringing along a portable, bottle sized Cliq Chair.
Friendly groups of gay men and solo wanderers stroll the beach throughout the day. So, while it may not have a crowded feel, there is always an opportunity to make a new friend. Attract some attention with a gorgeous striped red beach towel. It’ll get you noticed from far away!
Find a Private Pines Pool Party
Any local Fire Island gay visitor will tell you that some of the most memorable days are at private pool parties. These could be pool parties hosted in someone else’s house, to which you can find by making friends with locals, or they could be publicly advertised or promotional events.
Sometimes these private pool party events on Fire Island are publicized, especially so if it’s a for-profit event like the Summer Camp Open Swim Sunday Pool Parties hosted by Spray Fire Island in 2019.
Some years there are weekend pool parties advertised around The Pines, but the past couple of seasons I haven’t seen this as much.
The Fire Island Pines Gym
You may be on vacation, but that hasn’t stopped droves of muscled men from getting a workout in. The Fire Island Pines Pavilion has a small indoor/outdoor gym space that some guys use to get their blood pumping.
Large weights are in a covered outdoor area, not too far from the public pool deck. Cardio machines are indoors in an air conditioned space. Check hours and rates at the Fire Island Pines Gym Website.
If you prefer working out a little less publicly, there are so many quiet boardwalks to go running on. If you like guided workouts, definitely check out Aaptiv. They offer a 30 day free trial. I love their HIIT workout programs.
Fire Island Gay Clubs & Parties
Weekend crowds interested in Fire Island gay nightlife will typically stop home for their dinner after attending High Tea (known as “Sip and Twirl”) and come back a couple of hours later.
If you missed the earlier descriptions of Low & High Tea, scroll upward to the “Fire Island things to do” section.
Later in the night, the club on the Pavillion’s first level will open up. On most weekends during the summer season, there will be at least one party per weekend here.
However, there is no guarantee, so check events the Pavilion Website to be sure. If you plan to attend, remember that cover fees are usually cash only.
If you feel overwhelmed about finding the right Fire Island gay parties for your visit, don’t stress about it. Most likely, you will only find out about scheduled events after you arrive on the island.
During the summer months, there is always something happening. Often, you’ll see locally posted advertisements along the boardwalk for parties.
There’s also the famous karaoke night at the Blue Whale, a more tame option if you’re not up for dancing!
Cherry Grove Underwear Party
Every weekend, the Ice Palace Cherry Grove gay club hosts a legendary underwear party. There is an enormous dance floor, multiple bars and a rear deck space where everyone socializes. If you’re visiting The Pines for the first time, this party is a must!
Entering the underwear party, you will be given a drawstring backpack to put your clothes into, which you then check with an attendant. It is all very organized. The Ice Palace underwear party entrance fee is also cash-only, so don’t forget some money.
If you’re staying in The Pines, I recommend you plan to catch one of the final water taxis back (more on this in the travel tips section).
Alternatively, you can walk along a dark path through the dunes, passing the “Meat Rack” on your way home. I’ll leave this part of the adventure to you—go ask a local what it is!
Fire Island Pines Parties & Events
The Pines has become so extremely popular over the past couple of decades, that there are several yearly events that you should consider attending.
First-time Fire Island gay travelers shouldn’t prioritize planning their trip during one of these events in my opinion.
There is usually so much activity happening on regular summer weekends that you’ll be plenty busy. However, if you’ve been to Fire Island before, maybe it’s your time to try one out.
Pines Party: The Biggest Fire Island Gay Party Event
The Pines Party special gay event on Fire Island attracts an enormous crowd each summer. Many local gay New Yorkers love Pines Party and buy tickets far in advance.
The yearly Pines Party is quite an extravagant gay circuit festival. Colossal stage equipment is installed on the beach and big-name DJ’s are promoted for the giant party weekend. It’s a big deal!
Pines Party is known to be an intense gay event. If you’re planning to buy tickets, come prepared for bustling crowds of frenetic gay men on this tiny sliver of gay paradise.
Ticket sales typically start a year beforehand. While they can be quite pricy, many guys wouldn’t miss Pines Party for anything.
The Invasion of The Pines Event
A yearly event called “The Invasion of The Pines” is a prideful, celebratory ritual that dates back to the 70’s. In 1976, Terry Warren was refused service in a Fire Island Pines restaurant for being dressed in drag.
Upon hearing of such discrimination, Terry’s friends in neighboring Cherry Grove dressed themselves in full drag, took a boat to The Pines and stood their ground in what was called the first ever “invasion.”
Every year, Fire Island welcomes droves of drag queens from all over in performing a glorious repeat Invasion of The Pines. The Invasion event is held very dear to so many residents and frequent visitors of Fire Island Pines.
Fire Island Gay Travel Tips
Part of Fire Island’s charm is the disconnectedness and ability to feel oneness with nature. You won’t find certain modern conveniences here, and many people prefer it that way.
Boardwalk pathways don’t have lighting at night, so be sure your phone has enough battery to power its flashlight. Or, carry a nifty little camping flashlight while out at night. Otherwise you will be walking in complete darkness.
Depending on your mobile phone carrier and the number of visitors in the area, you may not have a cellular connection. Many locals are accustomed to leaving their phones back at their house and relying mostly on wi-fi.
Day Trips to Fire Island Pines
Day trips to Fire Island Pines from New York City are common and quite popular given how expensive rentals can be. Most Fire Island day trip visitors arrive late in the morning and catch one of the last few ferries that night.
Keep in mind the Sayville Ferry does not run overnight, so don’t miss the last one of the evening.
While I wouldn’t suggest this for just anyone, some guys do stay the entire night partying on the island and then take the first ferry back toward New York City in the morning. For the night owls and hardcore partiers, only do this if the weather is pleasant enough.
Waiting in the rain or cold for hours until the first morning ferry arrives can be an uncomfortable experience. If you’re thinking “I’ll just sleep on the beach,” think again! It’s illegal in this area and the police will find you.
Water Taxi Between The Pines & Cherry Grove
Not to be confused with the ferry that you take from mainland Long Island to Fire Island, there is a separate water taxi service that runs along the shoreline. The Fire Island water taxi stops at many different neighborhoods, including The Pines & Cherry Grove.
The FI Water Taxi can be very convenient, but their schedules are not as dependable as the larger ferries. Typically, the water taxi passes each location once per hour, however they sometimes skip an hour depending on demand, but without notice.
The fare from Cherry Grove to The Pines is $9 USD cash, unless you buy a ticket on their mobile app. Final boat service each night is usually around 3:00 AM.
I recommend that you always call ahead of time to verify when the next water taxi boat will depart from your location. Keep in mind that scheduled departures vary depending on if the taxi is headed eastward or westward.
Looking for a more elegant and luxurious summer getaway? Explore the nearby Hamptons with wolfyy’s Hamptons gay guide.