Fire Island vs. Montauk: The Ultimate Long Island Getaway

Intro

This is the second installment on my series about things to do in and around New York City. In the previous post, I did a deep dive on Coney Island, and everything it has to offer, especially in the Summer. But now, we’re going to explore a couple of destinations located in Long Island, that long strip of land to the East of New York City. Fire Island and Montauk are our chosen escapades in this island, the first one being almost an annual tradition to do sometime in the Summer, and the second one being a bucket list spot for me for a while. Let’s explore them together!

On my way to Fire Island

Fire Island is a narrow barrier island off the southern coast of Long Island, New York, known for its stunning beaches, car-free communities, and vibrant mix of nature and culture. Stretching about 30 miles along the Atlantic Ocean, it offers a unique escape from city life, with sandy dunes, maritime forests, and a laid-back atmosphere. The island is home to charming seaside towns, lively LGBTQ+ communities, and family-friendly spots, making it a diverse destination for visitors. Accessible by ferry, Fire Island blends rustic tranquility with nightlife and social energy, all while preserving its natural beauty within the Fire Island National Seashore.

There are basically 2 towns that are the most LGBTQ+ friendly: Cherry Grove and Fire Island Pines (or The Pines), the last one being more gay/male friendly. But both towns are a haven for any queer people regardless, and probably the safest for this community in the US.

To go there from Brooklyn, we must take the LIRR to Sayville. In our case, the Jamaica station was the best solution as a start point. This is how it looks on the TrainTime MTA app, where tickets can be purchased also.

After almost an hour, we were in Sayville. There are shuttle buses that for a small fare would take you to the Ferry Station from the LIRR station. From here you can tell the vibes and the crowds coming into the island.

Tickets are sold over here in these cabins, and the Ferries go to Cherry Grove, Fire Island Pines and Sailors Heaven. Prices and timetables vary so just check the website, and schedule your train as well accordingly.

The ferry ride on that bay is quick, and smooth. There are no big waves or tides, so I do not think you have to worry about dizziness. There are sits inside and outside as well.

Leaving Long Island to go into Fire Island…

And quickly Cherry Grove is on sight, with the iconic Belvedere Guest House for Men to the very left. I can’t wait to walk the little paths on these towns and check the design and architecture of these beach houses.

Finally arrived to Cherry Grove for our 1-night stay at this island. The flags mark what Fire Island is all about. If you are not into any of that or spew hate you better do not get close here, otherwise everyone is welcome!

Beach, pool and Drag Shows!

What a really great weather on this August day in Fire Island. We chose to stay in The Grove Hotel since it was more affordable and had the option to do one night only. Many places allow a minimum of 3 nights, which is usual for many groups of friends. They can also be very expensive and sell out quickly. I would recommend start checking for hotels and houses in January before your Summer trip.

We arrived, got ready, and went to enjoy the beach. Nudity is not allowed but it is very common to see. There are park rangers policing the beaches, so maybe do not try to do anything naughty, but for example we saw people fully naked just laying down and enjoying the sun. So yeah, it is up to you to decide what to do.

In one of my previous posts, I talked about Fire Island, but also mentioned Gunnison Beach in New Jersey, as an alternative, also very gay beach, where nudity is allowed 100%.

Back in the hotel and after a shower, we enjoyed the mid afternoon Drag Show in the Ice Palace (basically the same building as The Grove Hotel), and it was really fun. They did many covers of Disney songs and of course I was living haha.

And of course I had to get a hot dog from the Pup Dogs at the event haha. Our lunch this day were some Italian subs that we got at the grocery store in front of the Ice Palace, and ate at the beach. They were really good. Expect way higher prices in the island compared to New York City.

For example these drinks were in the $20s range. Yikes. To be fair, these ones particularly were very strong. So yeah, expect more alcohol than usual.

A night at The Pines

Fire Island Pines is a 20 min walk away from Cherry Grove, through the Meat Rack, basically a small portion of land separating the two towns. This area is famous for cruising, although obviously not allowed. But if you want to skip the walk, you can take the Fire Island Water Taxi, although be aware of the times since they stop working at different times every night.

The epicenter of the action in The Pines is The Pavilion, a building with many elements on it, including a bar, where we were for a bit. Not much was happening this Sunday night, so instead walking through the Meat Rack again, we took the last water taxi, really quickly back into Cherry Grove.

A chilly second day

Even in the middle of the Summer, you can encounter days where it is not optimal to go to the beach, and the Monday where we were checking out was that kind of day. We still went to check the beach, and some people were in there lol.

We skipped breakfast kinda, and went to have lunch to Cherry’s on the Bay, where I got the grilled salmon. Love eating fish when I am by a beach.

We were just chilling after check out, and went to the Ice Palace to get more drinks, and then we got a milkshake from Sweet Licks.

Because of the weather we chose to head back home earlier than expected. It was also a Monday, and the next day we had to work so we took the ferry, then the shuttle and got to the station. This was our original plan:

We got to the Sayville station just to find out that the upcoming train could not come because there was an empty train stuck up front. We had to wait for more than an hour for the train to come. The alternative, an Uber to NYC would have been more than $150. We waited. But regardless a more chill second day, we enjoyed our time in Fire Island. I would recommend going in July for better weather, and on the Weekends if you like more crowds of people and ambience/events.

On the way to Montauk

Montauk, perched at the eastern tip of Long Island, is a seaside town that blends rugged natural beauty with a relaxed coastal charm. Known as “The End,” it’s surrounded by the Atlantic Ocean and Block Island Sound, offering pristine beaches, dramatic cliffs, and iconic landmarks like the Montauk Point Lighthouse. Once a quiet fishing village, Montauk still carries its maritime roots with fresh seafood shacks and a working harbor, but it’s also become a popular getaway for surfers, beachgoers, and city escapees. With its mix of scenic state parks, lively summer scene, and peaceful off-season calm, Montauk captures both adventure and tranquility in a uniquely timeless setting.

The way there is longer, almost 3 hours from New York City, in the LIRR. I was up early, and went to Jamaica to take the express train that would take me to Montauk.

After a long time on that train, in which I was basically seeing YouTube videos and playing TwoDots, I finally arrived in Montauk.

After getting there, I though moving around was going to be easier, just taking Ubers everywhere. But a 10 min ride from the train station to the Lighthouse was almost $80. I gasped. Checked Lyft, and the same. I waited a few minutes for the prices to maybe drop, and eventually the Wait and Save price dropped to $35 and immediately took it. Made it to the iconic Montauk Point Lighthouse and Museum.

Montauk Point Lighthouse and Museum

The entrance is not expensive but the museum is interesting. The line to go up the Lighthouse can get really slow though. Do not rush to do it at the end of your visit, cause you would have to wait a lot.

On the way up, a plaque with the name of Steven Spielberg caught my attention. I thought that maybe he was related to Eternal Sunshine of the Spotless Mind, movie filmed in this town, and that made me wanna come her many years ago. But, I checked and he was not involved.

After going up some narrow staircase, we made it to the top, where the views of a Labor Day chilly day were waiting for us.

We could also see the Easternmost point of the State of New York, full of fishermen and visitors.

The park was full of visitors, probably because of the holiday, but also because it was the last day of the calendar Summer. A quick escapade before classes and work starts is always good.

Just like mentioned earlier, some cliffs are located at this tip of Long Island, making it look very dramatic from some angles.

After standing in the top platform, there was an additional step we could go up, to see the bulb of the Lighthouse and more views, although more enclosed.

Finally it was time to come down. The whole thing took a long time, since everything had to be done slowly and safely.

Back in the Museum area, there were more exhibitions. There was also a very large gift shop. One of my friends told me that they spent some time in Montauk but never came to the Lighthouse. I find that hilarious. It’s the must do!

Easternmost Point of New York State

Standing on these rocky bluffs, you’re truly at the edge of New York, where the Atlantic Ocean stretches endlessly and powerful waves crash against the shore. It’s both a scenic and symbolic spot—known as “The End”—where visitors come to take in breathtaking sunrises, whale-watch in season, or simply experience the sense of being at the farthest reach of the state.

Lots of fishermen in this area.

And of course the Lighthouse was magnificent on the top of the cliff.

Ditch Plains Beach

Time to leave the Lighthouse, the farthest place I was going to go to today, and now I had to figure out how to get to my next destination in Montauk. Phone service here was terrible, so I struggled to get an Uber, and then the line for the car to get into the park was long. Wasted a long time here. However I was finally able to get on the Uber and head to Ditch Plains Beach.

Ditch Plains Beach in Montauk is a beloved stretch of shoreline famous for its laid-back vibe, golden sand, and some of the best surfing waves on Long Island. Just a short drive from Montauk village, it’s a favorite spot for both seasoned surfers and beginners, with long rolling breaks and a friendly surf culture.

Beyond the waves, the beach offers wide open space for sunbathing, beach walks, and picnics, with food trucks often parked nearby serving casual bites. Surrounded by dunes and natural beauty, Ditch Plains captures Montauk’s unpolished charm—making it a go-to destination for those seeking both adventure in the surf and relaxation by the sea.

Lots of surfers were here on this chilly Labor Day.

It was time for lunch, and decided to eat something from Ditch Witch, a famous food truck on this beach.

Grabbed the poke bowl with ahi tuna. That was sooo good.

Leaving Montauk

I had spent most of the day on the Lighthouse and Ditch Plains Beach, but now it was time to explore the village a little more. I was surprised on how cute it was. I grabbed a coffee and started walking around.

After walking for a while I noticed a free shuttle to the train station. One of the timetables had a train going into the city soon, so I decided to go on that one. This concludes my visit to these two spots in Long Island. Which one did you like the most? Comment below.