7 ways to upgrade your New York City holiday

Oct 17, 2020

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Editor’s note: As the travel industry reopens following COVID-19 shutdowns, TPG suggests you talk to your doctor, follow health officials’ guidance and research local travel restrictions before booking that next trip. We’ll be here to help you prepare, whether you’re travelling next month or next year.


One look at the average nightly hotel rate or nearest dinner menu, and you might think the only way to have an affordable trip to New York City is to pack a backpack filled with granola bars and sneak onto the nearest walking tour.

It’s true that a trip to the Big Apple can come with a big price tag, but you don’t need to drain your savings account or sleep on the subway to make it happen. In fact, travellers can take a page out of any savvy New Yorker’s notebook and have an elevated, downright luxurious trip to New York City for less than the average visitor.

All you have to do is plan ahead — trust us.

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Get elite benefits at a luxury hotel

(Photo by Melanie Lieberman/The Points Guy)
(Photo by Melanie Lieberman/The Points Guy)

Sure, you can redeem points for a completely free night (or more) at a dizzying number of hotels all around New York City. But if you really want to feel like a VIP guest, consider booking through American Express Fine Hotels & Resorts,  if you have either The Platinum Card from American Express or The Business Platinum Card from American Express in your wallet. You can use Membership Rewards points to book your room (read: stay for free), or you can choose instead to earn points on prepaid bookings. Either way, you’ll get exclusive perks like daily breakfast for two; a room upgrade upon arrival, when available; midday check-in, when available; guaranteed late check-out; and a $100 property credit (which might be redeemable at the spa or at on-site restaurants) among others benefits.

More than two dozen luxury New York City hotels participate in the programme, many of which can’t be booked through any other loyalty programme such as The Carlyle, a Rosewood Hotel; the Baccarat Hotel New York; the first-ever Equinox Hotel in Hudson Yards, the Four Seasons and the storybook-worthy Plaza.

Score a seat to the biggest shows (for a bargain)

(Photo by NAO/Twenty20)
(Photo by NAO/Twenty20)

Few activities scream “fancy weekend in New York City” quite like a Saturday night performance of the most talked-about production in town. But even terrible seats at the most in-demand shows can easily cost upwards of $500. I’ll admit that, in desperation, I’ve paid more than that for tickets in the past. Don’t be like me, though! With a little patience and planning, you can save big on theatre tickets. And really lucky travellers might even score tickets for free.

You can find reduced prices on same-day tickets (up to 50% off) at the TKTS booths in Times Square, South Street Seaport and Lincoln Center — if you’re willing to get out of bed early and wait in line. During Broadway Week, which happens twice a year, you can buy two-for-one tickets to select shows. There’s also the TodayTix app, which helps you find discounted tickets up to a month in advance (or more). And if you’re travelling with little ones in tow, Kids Night on Broadway (KNOB) lets you buy an adult ticket and receive a free ticket for a child 18 and under (actually, the tickets will show half-price for each of you).

There are also a number of shows (Harry Potter and the Cursed Child; The Lion King; the Book of Mormon) that offer a daily digital lottery. And depending on what credit cards are in your wallet, you may have access to cardholder-only presale tickets. How else do you think I was able to afford to see Hamilton?

Related: A beginner’s guide to New York City: Everything you need to know for your first trip

Skip the line at the most popular venues

(Photo by Paisley/Twenty20)

They say time is money, and you can save a lot of both if you sign up for Clear in advance of your New York City holiday. You can use it to breeze through security at all the New York-area airports — JFK, LGA, EWR and Westchester County (HPN)— and also skip the lines before a sporting event or concert at Citi Field, Yankee Stadium and Madison Square Garden.

Skip public transportation

(Photo by johnny5ived/Twenty20)
(Photo by johnny5ived/Twenty20)

Riding the subway is a right of passage, and can often be faster than trying to hail a cab. But it’s definitely not the most glamorous way to explore the Big Apple.

But I think we can all agree that a serious upgrade to your New York City holiday means skipping the traffic altogether with a luxury helicopter ride. You can use your Uber app to book a ride to New York-JFK for an eight-minute trip from Manhattan (sure beats sitting in traffic for an hour or taking the AirTrain). Or, try Blade, which sells seats to JFK, LGA and EWR from $195.

Get a free scenic boat tour

(Photo by Wyatt Smith/The Points Guy)
(Photo by Wyatt Smith/The Points Guy)

If it’s your first trip to New York City, you’re probably looking forward to taking a scenic boat ride around the harbour. But you can avoid the touristy sailings (which will often set you back at least $20 per person) and ride the free Staten Island Ferry instead. You’ll get the same iconic views of the city skyline and the Statue of Liberty without paying a dime. The ferry runs 24 hours a day, seven days a week, every 30 minutes — and even more frequently during rush hour.

Dine at the hottest tables in town

(Photo by barrelofthelens/Twenty20)
(Photo by barrelofthelens/Twenty20)

Let’s get this out of the way: You don’t have to spend a fortune to eat well in New York City which, after all, is famous for its $1 slices of pizza, $6 burgers from Shake Shack and other inexpensive carbohydrates. But this sleepless city is also home to some of the greatest fine-dining institutions on Earth, and if you really want to travel like a VIP, you should carve out time for at least one over-the-top culinary experience during your trip.

Use your Platinum-branded card from American Express to access the Global Dining Collection: upscale restaurants around the world that partner with Amex to offer cardholders premium dining experiences such as special menu items, free drinks and prime reservations. Yes, even tables at restaurants that are otherwise fully booked online. There are more than 40 participating restaurants in New York City, including Eleven Madison Park, Carbone, Blue Hill and Gramercy Tavern.

Post up by the pool

(Photo by Melanie Lieberman/The Points Guy)
(Photo by Melanie Lieberman/The Points Guy)

Here’s the thing about summers in New York City: They’re hot. Really hot. So while lounging poolside may not be the first thing that comes to mind when you’re imagining a trip to New York, it can be a great way to spend an especially hot day during the summer. New York City is home to some incredible hotel pools, and you don’t need to splash out for a room to get access.

At the Equinox Hotel Hudson Yards, for example, you can hang out at the buzzy outdoor heated pool and roof deck by getting a day pass to the gym, or booking a spa treatment. At the James in Soho, you can post up by the pool for free during late-afternoon weekend pool parties. There are also day passes available for the resort-inspired pool at the Dream Downtown and The William Vale (spring for a two-person pergola for $100 on weekdays).

Bottom line

You don’t need to take a second mortgage out on your home to enjoy New York City like a VIP. With some careful planning and a few careful splurges, you can experience a truly upgrade version of this sleepless city for a fraction of the price. And remember, a New York City holiday will also be filled with opportunities to earn bonus points and miles, so prepare your wallet accordingly to really maximize the experience.

Featured photo by fabien.bazanegue.photography/Twenty20.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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