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Race to the Hamptons: What's the Best Way to Get There?

June 06, 2019
21 min read
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It's a Friday afternoon in New York, and everyone has a place to be. Slowly but surely, office workers around the city start to filter out around 2pm. Collars are loosened, ties removed and office heels give way to sensible flats and beach-friendly sandals. It's time to relax and party, not labor over more spreadsheets.

The last place you want to be is stuck in traffic for six hours on the way to a weekend at the beach.

In the name of helping Gothamites make the weekend come faster, we at The Points Guy sacrificed a weekend of our own testing out five different ways to make it to the popular East Coast beach destination the Hamptons. Sure, summer Fridays may have taken off in the 1960s so that workers at New York City publishing houses could beat rush-hour traffic to the Hamptons in their cars, but what's the best way to make it to the Hamptons in 2019?

The 21st century has brought a lot more choices than cruising along the Long Island Expressway in a 1965 Cadillac Coupe DeVille. You can still drive or take a train, of course, but now there's the Hampton Jitney, a luxury bus and even a helicopter — BLADE express service to the exclusive, oceanfront enclave for those who like to see and be seen in the summer.

For our test, we decided to simulate a typical summer Friday commute to the Hamptons, testing different forms of transportation. We started our race from a central point in Manhattan's Union Square and finished at a house about a 10-minute drive north of the East Hampton train station.

Taking the lead from our first race, to Washington, DC, we decided on five modes of travel: the Long Island Rail Road’s express Cannonball train departing from Penn Station at 4:06pm, a Blade helicopter departing from an east Manhattan heliport at 3:30pm, the Hampton Jitney and Hampton Luxury Liner (both private bus companies) departing from Midtown East at 3:50pm and a rental car from nearby Union Square.

My fellow competitors were TPG staffers Nick Ellis, Samantha Rosen, Jake Nankin and Danielle Vito. At 2:45pm, all five of us met in Union Square to begin the race to our rented house in the Hamptons.

What follows is our tale of Friday afternoon's adventures.

Car: Nick was feeling really good about his chances as the race got underway. Union Square was just a couple of blocks from where the car, a 2018 Range Rover Velar, was parked, and it took less than five minutes to get to the garage and retrieve the car. That, however, was Nick's last triumphant moment for at least a couple of hours.

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Jitney: Sam began her luxurious journey the way all luxurious journeys begin: the New York City subway. From Union Square, she took the 6 train up to 59th Street with a minor snafu at Grand Central (the train was having mechanical issues). Things were not going well.

Luxury Liner: After finding out the night before that the 3:50pm bus was canceled and he had been moved to the 4:50pm bus, Jake had time to kill before needing to be at the bus stop on 38th Street and Lexington Avenue. He decided to make his way uptown on foot, stopping halfway to enjoy a cold beer at a rooftop bar.

Train: After a quick subway ride and walk from Herald Square to 34th Street, Brendan was in the armpit of New York City’s transit system: Penn Station. Penn was a hot, sweaty and crowded mess when he arrived. While passengers crowded around, waiting for the Long Island Rail Road, he grabbed a bagel and water and settled into a seat at Starbucks.

Helicopter: Danielle hopped in an Uber and got stuck in quite a bit of traffic. For what's typically a 10-minute ride, it took her 27 minutes to get to the Blade heliport at 34th Street. This was frustrating, since she wanted to hang out in the lounge beforehand. #FirstWorldProblems.

Luckily, she had just enough time to grab a cocktail at the bar, which they put in a cute, plastic wine glass with a lid so passengers could take drinks to go. The drinks were complimentary, as they should be when you pay $795 for a ride to the Hamptons.

Car: Nick fought traffic for the 10 blocks that lay between the parking ramp near Union Square and the Queens-Midtown Tunnel, and he made it to the tunnel entrance just a few minutes past 3:30pm. The tunnel was a traffic jam, though, and things were no better on the other side. And since there was no one traveling with him, he decided that it was time to break into the road-trip snacks. First up were the sour gummy worms.

Jitney: Snafu and all, Sam had plenty of time to spare before her 3:50pm bus. She had a big decision to make: Should she bop around in Bloomingdale’s or Sephora for 20 minutes? She opted for Sephora and did a little touch-up, as one does before heading, as they say, Out East.

Luxury Liner: Jake found a nice spot in the sun and watched some of the French Open on the bar TV while enjoying his lager. More than once, he questioned the randomness of how the modes of transportation were assigned.

Train: After chowing down on his bagel, Brendan still felt like he'd need provisions for the ride. He headed into Duane Reade and grabbed two Bud Light tall boys. Nothing fancy but economical, just like the train ride, which cost him $30.50. As he was checking out, his train's track was announced and the hordes of weekend warriors swarmed toward the train. He rushed to the tracks and lined up to board the locomotive.

Helicopter: Danielle and two other passengers were escorted out to the helicopter. The Blade helicopter was much more luxurious than the tour helicopters she’d taken before: sleek, leather seats, Bluetooth-enabled headphones and complimentary water in the center console.

Danielle was excited to fly over LaGuardia Airport (LGA) and had a major AvGeek moment as she snapped a few aerial photos of Delta aircraft. Her co-workers would be proud, she thought as she sat back and watched the views as she glided over Long Island.

Car: The city was finally in the rearview mirror, but things were still slow going. Since he'd left the parking garage, the speedometer on Nick’s rental car hadn’t exceeded 15 miles per hour.

Jitney: After two other Jitneys rolled on by, the one heading toward East Hampton finally arrived. It was the moment of truth, but, hey, Sam thought: If it was good enough for Samantha Jones, it’s good enough for Samantha Rosen.

Pro tip: Listen to the Jitney people when they hop off and tell you where it’s going. You definitely would not want to get on the wrong one.

Luxury Liner: With roughly an hour to go, Jake finished the walk uptown and — oh look, another bar! He figured he had time for one more before the bus was scheduled to leave, so he settled into a seat at the bar and ordered another round.

Train: Fortunately, the train wasn't as crowded as expected. Brendan was warned by more experienced Hampton habitués that it's usually standing room only on the Cannonball, an express train that runs once on Friday, departing at 4:06pm and skipping all stops until it reaches Westhampton and ending in Montauk. He grabbed a seat and settled in for the two-hour ride.

Helicopter: Thirty-three minutes after takeoff, Danielle touched down in East Hampton. Danielle didn’t have phone service for the majority of the flight, so when she landed, her phone went off with the a half hour's worth of texts from the other racers. Some of them hadn't even left New York City yet. How sad. Danielle called an Uber from the heliport, and she headed on her way to the Airbnb.

Car: Nick was on the Long Island Expressway, still 55 miles away from the next step in his directions, and he passed a particularly triggering sign that read “Utopia Parkway.” This drive, in fact, was the farthest thing from a utopia. And the gummy bears were already about half gone. At least it was sunny, though, and the playlist that Nick made was really coming into its own.

Jitney: Sam finally made it out of Manhattan and could attest that "the Jitney is like the bus to summer camp, only instead of singing songs, everyone speaks on their cellphones and ignores each other." She was half expecting people to start singing “One, two, three, four, we want Color War!” but everyone was too busy scrolling through Instagram.

Luxury Liner: Jake closed out and made his way over to a bodega to stock up on snacks for the ride. After grabbing chips and a large water bottle, he was officially ready to get on the road. He walked over to the stop and joined a few other passengers as they awaited their ride out east.

Train: After departing right on schedule, someone grabbed a seat right next to Brendan so he wouldn't have as much room to lounge about. The train made a few unexplained stops, just sitting on the tracks but not letting anyone off. By 4:30pm, it had reached Jamaica, Queens.

Helicopter: Danielle pulled up to the Airbnb (the official finish line) at 4:28pm. She snapped her victory photo and sat out in the backyard to wait for the rest of her co-workers. As TPG's social media producer, she was responsible for sharing the race updates to the brand's Instagram story. Danielle enjoyed watching the flood of videos and photos come in from the other racers as she laid back on a lounge chair.

Car: The traffic was thinning ever so slightly, and the weather was improving, so Nick felt it was time to open the windows -- and the panoramic sunroof. Even though traffic was still moving at a snail's pace, the city was giving way to the suburbs, the windows were down, and he was content. There’s nothing better than a road trip in the summer with good music (and snacks) to keep you company.

Jitney: Sam was still in Queens. But did not feel like a queen in all this traffic. The Jitney “counselor” passed out small water bottles and snacks, and even though she came prepared with her own, Sam appreciated the gesture.

Luxury Liner: The 4:50pm bus was nowhere to be found as the clock ticked past 5pm. Passengers started to become annoyed, and one decided to call the company. Passengers were assured the bus was on its way. Jake decided to pass the time by opening the chips he bought for the ride.

Train: Those worrisome pauses on the tracks and Brendan's fears that his second-place finish was in jeopardy were abated as the train started to pick up significant speed and fly by houses and cars. It was time to crack open a beer (it's legal to drink on the LIRR) and settle into the journey.

Car: Things weren’t improving at all on the traffic front, so it was high time for Nick to open the Pringles. Danielle had been at the house for about an hour at this point, and Brendan was nearing his train's first stop in the Hamptons. Nick was confident at this point, though, that he’d be the third-place finisher, as the two buses were quite a ways behind.

Jitney: The vehicle drove past Sam’s hometown of Roslyn. Then she realized she'd left the office three hours ago and was only 20 miles outside of the city. She considered making a petition for the Jitney to stop at Kitchen Kabaret and then realized she didn’t want to run into everyone she went to high school with. Petition aborted.

Luxury Liner: At long last, Jake was settled into his seat and on his way to East Hampton. With last place all but guaranteed, he plugged his headphones in and tried to get some rest.

Train: By this point, Brendan was well ahead of the pack. He grinned as he opened Google Maps and saw he was more than halfway to East Hampton, passing through the hamlet of Center Moriches. Those in buses and cars had been left in the dust, having to fight through Friday rush-hour traffic.

Car: Nick was still chugging along on the LIE and finally hit speeds in excess of 50 mph, and then saw a sign for the Long Island welcome center and immediately knew that he had to stop to use the restroom and buy a bottle of water, which he foolishly neglected to bring along from the city. Sam’s Jitney driver was finding his groove at this point, though, and Nick’s stop would prove to be costly.

Google Maps told him to take the road less traveled in order to avoid an accident on the LIE. As a result, Nick fell behind in a big way. Sam’s Jitney driver, a veteran of this route, knew to stick it out a little bit longer on the LIE, and she pulled ahead. Nick had moved onto Route 27 and hit a lot of traffic lights. But he wasn’t going to let the bus beat him.

Jitney: By the time she reached Dix Hills, Sam started to really catch up to Nick. Things were on the upswing. We’ve got ourselves a race here, ladies and gentlemen!

Luxury Liner: After cruising through the Midtown Tunnel, trouble arose in the form of LaGuardia traffic. Jake again wondered how he was lucky enough to be put in this situation, as Danielle had been at the Airbnb for quite some time now and Brendan was approaching quickly. Time to try to nap again.

Train: After passing through Westhampton, Brendan pulled into the Hampton Bays train station. He knew he'd be in East Hampton in no time, with just a few minutes to go, so he pulled out his second beer as the other competitors (well, except Danielle) were still much closer to the New York City than they were to their final destination. He enjoyed Nick and Samantha's text-based trash talk via cellphone while he was smoothly sailing through Long Island's more picturesque regions.

Car: Sam and the Jitney were now on the same road, albeit several miles apart. Nick knew in the back of his mind that he’d catch up and eventually pass Sam, since she was going to stop a few places before making it to East Hampton and then would have to take an Uber from the bus stop to the house. However, she was still very far ahead at this point, and Nick was having visions of losing to a coach bus that had left over an hour after he did. Talk about a New York newb.

Jitney: The Jitney pulled ahead of the car!

“Eat my dust, Nicholas!” Sam thought to herself from the bus the size of a New York City studio apartment.

The catch? She still had to stop three more times before the bus got to East Hampton.

Luxury Liner: After a short nap, Jake woke up as the bus was fully stopped somewhere on the east side of Queens outside of an AMC. After roughly five minutes, the bus began moving again, but it was officially time to wonder if Jake was going to make it time for the racers' 9:15pm dinner reservation.

Train: As Brendan was nearing his train stop, he grabbed his bags, pulled out his phone and opened the Uber app. The house was little ways from the station, so walking wasn't going to be part of the equation. Plus, the train was a few minutes behind schedule, so he'd need to gun it to make the best time.

Car: Nick finally reached the Hamptons, but there were still several towns to drive through before reaching the house. The speed limit decreased from 55 mph to 30 mph, and there was a slow-moving truck directly in front of him. There was nowhere to pass, either. One lane on each side. It was going to be close.

Nick had just moments before he passed Sam once again, though, and it looked like he was in the clear. But, considering the way her Jitney driver was driving, nothing was guaranteed.

Jitney: It was so close between Sam and Nick that she was looking out of her window on the Jitney for the car. The Jitney made a pit stop at a Starbucks parking lot for reasons that were unclear, since only a handful of people got out of the car … and the Starbucks was closed. Wasting precious time, people!

Luxury Liner: If Jake was going to be stuck on this bus for another couple hours, he figured he might as well attempt to get some work done. He tried logging on to the W-Fi, but when that didn’t work, he connected using his phone as a hotspot and knocked out some work, like the New York publishers of the 1960s might have.

Train: After a 10-minute Uber ride that cost about $20, Brendan arrived at the house at 6:55pm. Danielle was calmly waiting and in deep social-media mode. Brendan dropped his bags and grabbed a seat by the pool, ready to enjoy the weekend.

Car: Nick arrived — just as the sun was beginning to set — at the East Hampton house. It was a rather unceremonious entrance. Nick bursted triumphantly into the house to find Brendan and Danielle relaxing calmly by the pool, and they barely even looked up when he arrived. If you're not first, you're last, he guessed.

Jitney: Not only did Nick pull ahead, but he arrived at the East Hampton house while Sam's Jitney was still dropping other people off along the way. Womp womp. She was definitely feeling antsy.

Luxury Liner: Time to check out the snack bar! After quickly going through those bodega chips, Jake hit the snack bar at the back of the bus. Fully stocked with a variety of chips and water bottles, Jake realized the bodega trip had probably been unnecessary.

Jitney: After almost four hours of driving, the Jitney finally arrived in East Hampton … but the journey wasn’t quite over yet. Sam quickly ordered an Uber, and they shuttled off to the house. Sam finally made it a few minutes after 8pm and proceeded to melt into the couch.

Luxury Liner: To make sure he experienced all of the amenities the Luxury Liner had to offer, Jake decided to check out the lavatory at the back of the bus near the snack bar. While convenient to have on the bus, the bathroom was smaller than most airplane bathrooms and was not the cleanest.

Luxury Liner: Jake finally strolled into the Airbnb, just in time for dinner.

Key Takeaways

Car: While a car won’t get you there faster than a helicopter — or even a train — it is a lot of fun. There’s nothing quite like the feeling of freedom that comes with driving with the windows down on a summer day, blasting music, eating road-trip snacks and laughing with a group of friends. Plus, having a car gives you flexibility once you reach your destination to get groceries, pick up bagels in the morning and — most importantly — to leave on your own schedule.

Jitney: The Jitney will get you from Point A from Point B, but you'll have to sit in a bunch of traffic. It definitely won't be the most luxurious mode of transportation you'll ever take, either. Try to get on an early one, if possible, or prepare for a long ride out east. You also may or may not run into someone you went to high school with.

Luxury Liner: On a Friday afternoon, the bus is definitely not the way to go. Especially if you can make it in time for the express train. And even cancellation aside, it's not worth paying a small premium to take the "luxury" option. But, Jake could see the bus making sense during off-hours, when traffic isn't bad and the express train isn't running.

Train: The train is probably the best way to go, especially if you don't want to splurge on a helicopter. It's cheaper than the Luxury Liner and about the same price as the Jitney — but significantly faster than both, and you won't be at the mercy of Friday rush-hour traffic. The ride itself is smooth and the seats are comfortable, if you can get one, that is.

Helicopter: Is traveling by helicopter the fastest, most convenient and most luxurious? Yes.

Is it a reasonable option for the average person? Absolutely not.

Unless you're a CEO, trust-fund baby or you're picking dollars off the money tree in your backyard, a $795 ride out east is probably not in the cards. Danielle was lucky enough to have been able to experience the journey thanks to TPG, but as a 27-year-old middle-class woman, she would never be able to justify taking the helicopter. She would most likely drive or take the Long Island Rail Road.

Cost and Time Breakdown

*While the car was on the expensive end, we rented a nicer vehicle (a Range Rover Velar) through the car-sharing application Turo for a future review of the service. The total cost covered the two-day rental, taxes, tolls and gas. Turo is not yet available in New York, so Nick picked up the car in Jersey City, New Jersey, earlier in the morning. However, there are many rental car agencies in Manhattan that don't require the trek out to New Jersey.

Note that you'll also be able to split the cost of a car with friends and have the car at your disposal throughout the entire weekend.

To help offset the cost of a BLADE helicopter ride, you can use the TPG referral code: BRIANF&F and receive $100 in BLADE credit.


Bottom Line

Unless you have a boatload of cash to drop on a helicopter ride, most of the transit options are going to take a decent amount of time. No matter what, the bus and car are going to hit rush-hour traffic unless they leave very, very early. If you can catch the 4:06pm express train, that's likely your best option to escape the city. However, if you're on a local train, that can add an extra 40 minutes or more to your journey.

It's also important to note that if you do take a car, you can probably split the cost among friends and won't have to shell out for Ubers or taxis everywhere you go, which can help dissipate the initial sticker shock.

Our faces when Jake finally arrived!

Regardless of which option you choose, make sure to follow TPG for future exciting races, and let us know what you thought of our race to the Hamptons!

Feature photo by Monica Murphy / Getty Images.

Tables created by Wyatt Smith and Orli Friedman.

Featured image by Getty Images