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Fire Island gay travel is a heaven of drag shows, underwear parties and relaxation. Find Fire Island gay hotels, house rentals, beaches & events with wolfyy.

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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.

gay pines
gay pines
where to stay cherry grove

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 locals. The Fire Island Pines and Cherry Grove communities comprise the gay area of Fire Island, which you absolutely must visit at least once!

where to stay cherry grove

Before we get 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.

Fire island gay community
Fire island gay community
deer in woods

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. 

deer in woods

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.

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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.

private house fire island pines

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. 

home rental

If you are someone who absolutely must be in the center of the fun, then the Fire Island Pines neighborhood will probably be a better choice. In my opinion, first time Fire Island gay travelers should stay in The Pines.

private house fire island pines
fire island pines gay

Cherry Grove tends to have a slightly older population, but is truthfully just as popular. For those specifically wanting to attend the famous cherry Grove underwear party (more on this in the nightlife section), it may be more convenient to book a place in Cherry Grove. 

home rental
fire island pines gay

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 have never booked a place to stay in Fire Island Pines, there are several things you should know. Firstly, you will almost definitely reserve a single room in a shared house. Often, even individual rooms are shared, but usually among friends.

fire island gay travel

Firstly, you should join a Facebook group used for reserving rooms in Fire Island Pines. 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. 

fire island gay travel

Next, message people who have already posted availabilities. From here you can settle on details and payment, which usually will require some sort of deposit. 

Locals purchase what are essentially timeshares, where rotating groups of gay guys occupy a house each week of each summer month. These shares are frequently listed for re-rental in certain Facebook groups.

These “room shares” are the accommodations you are seeking to reserve. It is a bit complicated, but since there is such high demand and a lot of interested visitors, this is how Fire Island rentals are done!

pines gay travel
pines gay travel

The best place to find last-minute rentals and places to stay in The Pines is in a Facebook group called Boys of Fire Island. You will need to request admission to the group, but as long as you don’t seem like a robot or blank profile, you should have no issues getting access. 

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.

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Fire Island Pines Rentals on Airbnb

Depending on how far in advance you are looking for your place to stay, Airbnb might be a viable option. For last minute trips, you might find that Airbnb options are expectedly slim. I would still do a search though. Here’s the best area for Fire Island Pines Airbnb listings.

fire island airbnb rental
airbnb rental
fire island airbnb rental

Some owners or those selling shares prefer Airbnb’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 Airbnb or the Facebook groups.

airbnb rental

Fire Island Gay Hotels

For those not familiar with the types of accommodations in The Pines and Cherry Grove, take note that there is no such thing as a Fire Island gay resort, or anything similar to that. The Fire Island gay areas are small and residential. The only hotel in The Pines is the one mentioned above.

Cherry grove hotel

Cherry Grove’s hotel has a much better reputation. Home of the famed Fire Island gay underwear party, the Grove Hotel, also is a fantastic place to stay in Cherry Grove. The Grove Hotel is adjacent to the Ice Palace Nightclub, where you can count on hysterically funny drag shows every weekend.

Ice Palace Fire Island
Ice Palace Fire Island
Cherry grove hotel

Lastly, I advise that you do not stay in 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

There is only one way to get to both The Pines and Cherry Grove, and it can definitely be confusing for a newcomer. So, read the following very carefully. I encourage you to bookmark this page for future use. While you’re at it, subscribe to wolfyy email alerts using the form at the bottom of this page.

how tp get to Fire Island Pines
how tp get to Fire Island Pines
ferry to fire island

You will likely be departing from Penn Station in New York City on the Long Island Rail Road. 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.

ferry to fire island

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.

walking on Fire island
boardwalk
walking on Fire island

Upon arrival at the Sayville LIRR train station, follow everyone toward the white mini-busses. 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

Upon arrival 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 is quite enjoyable! These boats have open-air top seating decks where everyone gets comfortable in the summer sun.

fire island ferry service

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.

fire island ferry service

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.

gay pool parties fire island
gay pool parties fire island
gay party fire island

One of my favorite things to do in Fire Island is to stroll the winding pathways and gaze at the wonderful architecture. Neighborhoods here boast such beautiful vacation homes nestled in the woods.

gay party fire island

To get yourself oriented, 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.

Low Tea at Pavillion

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. 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!

Low Tea at Pavillion

While 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! 

pool parties fire island pines
high tea FIP
high tea FIP

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.

tea dance fire island

Where is The Fire Island Gay Beach?

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.

gay beach fire island
gay beach fire island

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. Compared to the bustling gay beaches of Maspalomas or Barcelona, gay men take in the daytime serenity and save their energy for vibrant evening festivities and partying.

gay beach fire island pines

If you’re embarking on your first Fire Island gay travel adventure, there are a few things you should know about “gay beaches” in The Pines.

tea dance fire island
fire island gay beach

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.

fire island gay beach

Since the gay pines community is so physically isolated, you will not even encounter any individuals selling refreshments 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.

gay beach fire island pines
pool parties fire island pines

The best thing about the beaches in Fire Island Pines is that they’re never overcrowded. There is always plenty of space to spread out, run around, or play beach games.

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.

Find a Private Pines Pool Party

Any regular Fire Island gay traveler 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.

Pool party in Fire Island Pines

Usually at least once per summer, you’ll hear about planned pool parties hosted or sponsored by LGBT-oriented organizations or companies. I’ve attended some super fun pool parties hosted by Callen-Lorde as well as Chappy App (which is now Bumble), for example. 

Pool party in Fire Island Pines
man in private pool
man in private pool

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.

Workout in the Fire Island Pines Gym

You may be on vacation, but that hasn’t stopped droves of muscly 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.

fire island pines gym
fire island pines gym
fire island gays

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.

fire island gays
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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 toward the “Fire Island things to do” section.

LGBT nightlife
LGBT nightlife

Later in the night, the club on the first level of the Pavilion 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.

fire island gay party

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 the next big party.

man floating on pool raft

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!

gay party

When you enter 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.

Since you’ll only be wearing your underwear, you may want to wear a fun-colored fanny pack to hold your stuff. Alternatively, you could stash your belongings in some awesome Nasty Pig Sport Socks.

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 gay 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 Gay 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. 

pines party fire island

For those planning first-time Fire Island gay travel, it’s not necessary to plan around 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

Each year, there is a special gay event on Fire Island called Pines Party. Many local gay New Yorkers love Pines Party, and buy tickets far in advance. An event that I’ve not personally been to, many of my friends rave about how they look forward to Pines Party each year. 

pines party fire island

The yearly Pines Party is quite an extravagant 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!

beach party

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. 

pines party outfits

Tickets for Pines Party go on sale well in advance. Sales typically start a year beforehand. While they can be quite pricy, many guys wouldn’t miss Pines Party for anything.

beach party
pines party outfits

The Invasion of The Pines

An event called “The Invasion of The Pines” is a prideful, celebratory ritual that dates back to the seventies. In 1976, Terry Warren was refused service in a Fire Island Pines restaurant for being dressed in drag. 

invasion of the pines

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.”

invasion of the pines

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.

beachgoer
beachgoer
Long Island sound

There are no lights along the boardwalk pathways at night, so be sure your phone has enough battery to power its flashlight. Otherwise you will be stuck 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.

Fire Island day trip

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. 

Fire Island day trip
man floating on pool raft

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 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.

water taxi Fire island

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. Check the FI Water Taxi Web Page for schedules and contact information or to download their mobile app.

Visiting Fire Island During COVID: Worth It?

Fire Island Pines and Cherry Grove are two resilient gay hamlets that have seen their share of bad times. But what about during this global pandemic? Should you still plan a visit to Fire Island this summer 2020?

While the normal jam-packed festivities like Tea and karaoke night at the Blue Whale are legally scaled back, there is still life on the island. It is certainly nothing akin to a typically, energetic pines gay summer, but you’ll still find a huge LGBT population out there.

Fire island COVID 19
Long Island sound

The Fire Island gay communities have improvised and made due with what they have. As reported in a recent New York Times Article on Fire Island Pines, many residents and visitors have switched to private dinner parties. While not everyone follows mandated social distancing rules, it is one of the few ways locals are making the most of this summer.

While New York State has done an exceptional job with containing the virus, there are still opportunities to contract COVID-19 among summer gatherings, especially as they move indoors during the evening. 

If you’re traveling, make smart choices. Have a safe, wonderful Fire Island gay adventure!

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Are you exploring NYC on your journey? Read the wolfyy New York City Gay Travel Guide.

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