Tuesday, January 31, 2023

Where To Stay In Cherry Grove Fire Island

Fire Island Pines Retreat

Fire Island Pines and Cherry Grove short tour

Enjoy incredible sea views at this decadent and welcoming Fire Island gay hotel or, as it terms itself, a gay retreat. There are a range of private suites that are quirkily decorated and have all the extras your heart desires. Community spaces include the saltwater pool, panoramic deck and a living room for when you just want to kick back.

Its right on the beach and offers a range of beach and outdoor activity gear for whatever you might want from your Fire Island stay. Theres also a food plan option, so if you dont want to go shopping you can pay $25 per day for unlimited food and drink. Come and stay at this retreat and you might seriously consider relocating to Fire Island.

The Fire Island Pines Gym

You may be on vacation, but that hasnt stopped droves of muscled men from getting a workout in, all wearing their tantalizing sexy workout clothing. 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 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? Ill help you decide! First Ill explain what each neighborhood is like, and then show you the way to book a rental.

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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 elses house, 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 its 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 havent seen this as much.

The Cherry Grove Beach Hotel

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Reopened in 2017 after extensive renovation work required by a fire that destroyed much of the building, the Grove Hotel is a charming clapboard building with peaked roofs decorating its skyline. It is right in the heart of Cherry Grove so a perfect destination for weekend visitors who want to be in the middle of the action.

Enjoy the good-sized pool before popping next door to the Ice Palace nightclub. Or if clubbing isnt your scene, there are plenty of nearby cafes, bars and shops to keep you entertained for your weekend .

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Best Hotel In Fire Island: Cleggs Hotel

This hotel in Fire Island is perfectly positioned to allow you easy access to the beach. It has a snack bar where you can grab a quick bite, and a terrace where you can enjoy the views. The rooms come in a range of sizes to suit every travel group, and are spacious and comfortably furnished.

Fire Island may not be the first destination that comes to mind when youre looking for places to visit in New York. Its tiny, a narrow strip along the coast, so there arent many choices when it comes to neighborhoods. In fact, there are only three main areas offering accommodation on Fire Island, and theyre all fairly close together.

The first area is Ocean Beach, and is the best option for travelers visiting the island for the first time. Its a family-orientated neighborhood with lots of restaurants, hotels and great beach access.

Bay Shore is another area worth considering. This area is actually on the mainland, just a 30-minute ferry-ride away from Fire Island, and is a great option for those traveling on a budget. Its in a less-touristy area, offering cheaper local prices and accommodation options as a result.

If youre looking for where where to stay in Fire Island with kids, the Ocean Bay Park area is a good option. This hamlet close to Ocean Beach is known for its relaxing and friendly atmosphere, and has a number of restaurants on offer.

Fire Island Gay Hotels

No matter where you are in The Pines or Cherry Grove, youll be surrounded by gay men. There is one gay hotel in The Pines and one in Cherry Grove, but there isnt necessarily any type of Fire Island gay resort.

The Grove Hotel is a fantastic place to stay in Cherry Grove. Its adjacent to the Ice Palace Nightclub, home to Fire Islands 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 its proximity, but Ive 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!

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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. Heres the best area for Fire Island Pines VRBO listings.

Some owners or those selling shares prefer VRBOs 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.

The Madison Fire Island Pines

The 35th Annual Invasion of the Pines by Cherry Grove – Fire Island, NY

The Madison is a more low-key yet much more glamorous option among the Fire Island gay hotels. Theres a modern and beautiful building set in a secluded compound that feels far away from all the comings and goings of the main part of town, even though its only a minutes walk.

Minimal white décor with blonde wooden floorboards creates a clean, contemporary and elegant feel. Every amenity you can imagine is present, from air conditioning and en-suite in every room, to pool decks and massages. After a days relaxing and pampering, you can stroll down to the beach and watch the sunset. Its a delightful retreat perfect for me time, or time with that special someone.

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Things To See And Do In Bay Shore

James Griffiths Photo

  • Play a round of golf in beautiful surroundings at the Southward Ho Country Club.
  • Pick up some bargains at the Westfield South Shore.
  • Indulge in local food in spots such as Maxwells, Bayside Clam and Grill Bar, or Captain Bills Restaurant.
  • Enjoy the ferry-ride across to Fire Island.
  • Explore the sports fields and multi-use trails at the beautiful Heckscher State Park.
  • Explore some of the local villages along the shore like Babylon or West Islip for a real small-town feel.

Cherry Grove Where To Eat Drink And Party

Sand Castle 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 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.

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Your Vacation Guide To Fire Island’s Cherry Grove And The Pines

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Fire Island has a long history as a bohemian summer retreat, and it is still a favorite of artists, writers, and actors. The LGBTQ community was welcome on Fire Island long before the watershed Stonewall Inn uprising and made the Pines and Cherry Grove their own. Vacationers of all stripes agree that the absence of cars and proximity to the water are the prime attractions. Secondarily, there are restaurants, clubs, shops and natural wonders to be enjoyed. Here is a guide to vacationing in these two iconic Fire Island communities.

Cherry Grove Where To Stay

A Beginners Guide to Summer on Fire Island

The Grove Hotel , 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 . Rooms in the palatial structure range from economy to luxury . Clothing is optional. Dune Point , an oceanfront guesthouse, has cutely decorated rooms and suites with kitchenettes.

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

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Fire Island Gay Bars Clubs & Parties

Firstly, in an ultra-gay destination like Fire Island, every bar is a gay bar and every club is a gay club!

Weekend crowds interested in Fire Island gay nightlife will typically stop home for dinner after attending High Tea and come back a couple of hours later. If you missed the earlier descriptions of Low & High Tea, scroll up to the things to do section of this guide.

Later in the night, the club on the Pavillions first level will open up. On most weekends during the summer season, there will be at least one party per weekend here.

Check events on the Pavilion Website to be sure, since theres no guarantee. 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, dont stress about it. Most likely, you will only find out about scheduled events on Fire Island after you arrive. Just make sure to bring along your best gay party accessories!

Karaoke night at a gay bar called Blue Whale is a tamer option if youre not up for dancing!

Fire Island Pines Parties & Events

Fire Island Pines has become so extremely popular over the past couple of decades, the community now hosts some incredible, huge gay events. Ill let you know all the best ones in the sections below.

While these events are always a blast, first-time Fire Island gay travelers shouldnt necessarily prioritize their trip to be during one of them, at least in my opinion.

With so many parties and events happening on regular summer weekends, youll still be plenty busy no matter when you visit!

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Cherry Grove Where To Play

Nightlife abounds. Cherrys on the Bay offers dinner and a show 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 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.

Fire Island Pines Architecture

What’s In a Name? (House Names in Cherry Grove, Fire Island)

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.

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Final Thoughts On The Best Places To Stay In Fire Island

If youre looking for a beach vacation from New York City, look no further than Fire Island. This lively area has everything from amazing beaches to a relaxing atmosphere, giving you the freedom to truly enjoy your vacation. And with our Fire Island neighborhood guide, youll easily be able to find the best accommodation options no matter what your travel style or budget!

And dont forget to take out Travel Insurance for your trip! I have been using World Nomads for some time now and made a few claims over the years. Theyre easy to use, professional and relatively affordable. They may also let you buy or extend a policy once youve started your trip and are already abroad which is super handy.

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Fire Island Pines Where To Eat Drink And Dance

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 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 , order a Blue Whale 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.

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Fire Island Restaurants Other Businesses Staying Open Into The Fall

Business owners have seen a steady stream of visitors on Fire Island despite the pandemic this summer. Credit: Linda Rosier

In a year when businesses have had to be flexible, the owners of several Fire Island eateries have banded together to offer visitors a reason to drop by after Labor Day weekend.

Initially, we struggled with the idea of staying open after Labor Day after an unusual season, says Jacquelyn Piazza, owner of Cherrys On The Bay in Cherry Grove. However, the decision to stay open was fueled by the support she and her fellow business owners received from visitors. “Our hope is that the weather will cooperate, allowing us to utilize our outdoor venues to offer our loyal customers a little bit of summer in September.”

Cherry Grove is not the only place where businesses are trying for a successful early fall. Chris Mercogliano, co-president of the Ocean Beach Chamber of Commerce and owner of both the Palms Hotel and CJ’s explains, We have been advocating all businesses to stay open as long as possible We feel with many people fleeing the city, Ocean Beach will be a viable destination through the fall.

Heres a breakdown of the suddenly plentiful options of things to do on Fire Island this September. Check fireislandferries.com for updated ferry schedules before you head out.

Ocean Bay Park Where To Stay In Fire Island For Families


Isabelle OHara

  • COOLEST thing to do in Ocean Bay Park Go parasailing and see the ocean from a whole new perspective!
  • BEST place to visit in Ocean Bay Park Take a tour through the beaches, dunes, and holly of the Sunken Forest.

Ocean Bay Park is very close to Ocean Beach and has a relaxing, kid-friendly atmosphere. This makes it one of the best places in Fire Island to stay for families. Its also close to the beach, and a number of bars, restaurants, and pizza shops.

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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. Its pretty much just one enormous outdoor gay bar!

The gathering for Low Tea officially starts at 5 PM and continues until 8 PM. Usually, by 6:30 or 7 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 PM, the crowd will pour to the adjacent pool deck, as well as toward the upper Pavilion deck.

High Tea is branded as a bar called Sip n Twirl. As the sun sets, the music gets around the pool gets louder and the night transitions to dance mode!

At Sip n Twirl, you can always count on a live DJ entertaining patrons on both the pool deck and upstairs.

While youre 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.

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 conductors instructions when he checks your ticket on the train.

If you are unsure which train, just ask someone near you. Most likely youll 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 prepared to cram in on busy summer times!

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