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How to plan an incredible trip to New York City

Here's a full breakdown of tips and tricks for booking - and enjoying - an awesome trip to NYC.

New York City is a dream destination, but planning out what to see and do in the "city that never sleeps" can cause some sleepless nights before you even book your flights. 

The city is infamously brimming with landmarks, restaurants, attractions, events, and spectacular sights - many of which have been rendered into true icon status. 

Compounding the sheer volume of marvellous sights and activities is the fact that the diversity of New York and its status as a global hub means that you can very likely indulge in any of several niche interests there, from Broadway musicals to ancient history to cutting-edge food or gaming.

Whether you've been a dozen times or are going for the first time, planning a trip from Vancouver to New York City can be daunting. Here's a full breakdown of tips and tricks for booking - and enjoying - an incredible trip to NYC.

Getting there: YVR to NYC

It's not hard to get to New York from Vancouver, but you might have to contend with a layover. 

Three major airports serve New York City: John F. Kennedy International Airport (JFK) and LaGuardia International Airport (LGA) in Queens, and Newark International Airport (EWR) across the Hudson River in New Jersey. 

Only two airlines fly direct from Vancouver International Airport (YVR) to New York: JetBlue offers one flight daily to JFK (and it's a red-eye), while Air Canada flies from Vancouver direct to Newark. 

If you don't mind running from one end of an airport to another (Montreal's YUL or Toronto's YYZ) then you have plenty of options for flights with connections.

To find the best deals, you may want to use a third-party booking site that can give you multiple options for trips. My trip was booked through FlightHub and I opted for two one-way tickets: A red-eye from YVR to LGA (through YYZ) on WestJet and LGA to YVR (through YUL) on Air Canada - the best options for my specific travel dates. 

For those who have not been to LGA in a long time (like me, until this trip) the airport has undergone significant renovations, and it is bright, modern, and packed with amenities. I have certainly spoken ill of LGA in the past but now would rank it one of my favourite airports I've travelled through of late. It's so nice to be pleasantly surprised. 

Getting from LGA to Manhattan

You'll need a different game plan for getting to your hotel from any of the New York City-area airports, but if you're looking to get from LGA to Manhattan, you have some great options. 

The free Q70 bus serves LGA and will connect you to the subway in Queens.

Many hotels offer shuttles as well. Taking a cab or Uber/Lyft is certainly an option, though take note that it could cost you well over $100 USD to do so.

However, Uber recently introduced a cost-effective shuttle from LGA to two transit hubs in Midtown Manhattan, Penn Station and Grand Central Station. 

Shuttles depart every 15 minutes (alternating between the two stations, so there's one trip per half hour to each) and cost just $18 per person. The pickup zone is outside the baggage claim area at both Terminal B and C (they're clearly marked). Be sure you book carefully to account for which station you're going to, which terminal you're being picked up from, and how many seats you are booking. 

The shuttles also connect the two transit stations to LGA on the same schedule. The ride is in a shuttle van and is operated by a licensed partner. 

If Uber cancels your shuttle, you will immediately have the option to book an Uber for free (minus tip and any tolls or surcharges). This happened for my Grand Central to LGA booking, and instead of spending $36 USD for the two of us to get to the airport, we took an Uber and were only billed $8 plus tip (USD). 

Getting around NYC

Besides walking, there is no better way to get around New York - for the most part - than on public transit. The MTA, which operates the city's legendary subway system, along with its buses, the Roosevelt Island Tram, and the Staten Island Ferry, may look intimidating but it is akin to a rite of passage for visitors to navigate. (Don't worry, even locals find themselves lost in the subway now and then - it happens!)

Your cellphone's map app will be able to give you transit details for NYC, down to which exit to use, and you can purchase a multi-day pass to enjoy unlimited rides. I found the best value was to get a seven-day Metrocard pass ($34 USD); with rides at $2.90 each, I think we may have broken even sometime around the afternoon of day two. A note: The MTA is working on phasing out the Metrocard (a swipe or dip card) for the OMNY, a tap-to-pay system akin to Vancouver's Compass card. You may use either for the time being (likely until 2027) with ease.

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Besides walking, the subway is the best way to get around New York City. It's affordable and can get you just about anywhere you want to go. JohnnyGreig/E+/Getty Images

Particularly in Manhattan, the subway is pretty much everywhere. Look for the green globes on posts next to staircases heading underground; you can also use the globes to figure out if that's the way you can go in. You'll also want to sort out if you're headed Uptown or Downtown, towards Queens, The Bronx, or Brooklyn, and if you need the local (makes all stops) or express (skips stops). 

Wayfinding has become significantly enhanced on the NYC subway in recent years, to the extent that newer subway trains have digitized displays in the cars that tell you where the exits and elevators are, and other pertinent information. 

Buses are also a great option for getting around; I only rode a couple this trip but found they were newer vehicles that were very clean and pleasant to ride in. 

Always be aware of changes in service and take into consideration that delays are possible. 

In NYC, you can book rides on apps like Uber, and you can also use taxis. To hail a cab, be sure to be on a street that has traffic heading in the direction in which you want to go. Step off the curb and raise your arm to signal to passing cabs; only cabs with their lights on are available to hail. 

Be sure to only use licenced cabs; avoid anyone in places like the airport baggage claim area who is approaching you and asking if you'd like a ride.

Where to stay in New York City

Location, location, location. Never has this been more true than in choosing where to stay when visiting New York City. 

My top priority for choosing a hotel was that it be very close to a subway stop (ideally one that serves multiple lines) and that it would be a good location from which to base our planned adventures. 

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The Moxy NYC Downtown is the only hotel in New York City that boasts an indoor basketball court guests can use. Located in the Financial District, the hotel is near several subway lines and central to many landmarks. My stay was booked through FlightHub. Lindsay William-Ross/V.I.A.

When travelling to a city as packed with hotel options as New York, sites that can isolate great deals while providing all the pertinent info you need to make a booking decision can come in handy if you don't already have a preferred hotel in mind. My hotel stay was booked via FlightHub, and I stayed at one of three NYC locations of a hotel brand called Moxy (which is part of the Marriott Bonvoy company). 

The Moxy NYC Downtown is located in the Financial District, steps from a major subway hub at Fulton Street serving numerous lines. The hotel is also close to some popular spots for visitors, like the World Trade Center and 9/11 Memorial and Museum, as well as the Brooklyn Bridge, and landmarks like the court buildings (in case you want to have a Law & Order moment).

Boasting NYC's only in-hotel basketball court (which you can book for some hoop shooting), the Moxy NYC Downtown is brimming with cool, playful vibes, from the help-yourself snack cart in the lobby to the lounge and bar/restaurant area that has live DJs in the evenings and all kinds of games to enjoy while hanging out. That said, the room was wonderfully quiet and the halls calm during my stay, which meant a terrific night's sleep - much needed with all the adventures and exploring on our to-do list. 

How to plan your NYC sightseeing and activities

Divide and conquer is the way to go, as in split everything you want to do up by neighbourhood. Be sure to factor in transit times, and when and where you might need an extended time to rest your tired feet and use the restroom (public washrooms are hard to come by in New York when you are out and about). 

New York is packed with quintessential tourist experiences, which can be as simple as taking in the sights and sounds of Times Square or as specific as booking a time to experience an attraction like the Top of the Rock viewing decks at Rockefeller Plaza. While much of New York can be enjoyed at your own pace, like a stroll through Central Park, many of its treasured venues require tickets and time slots. 

I must admit, I took my New York planning so seriously that I made a spreadsheet. 

This allowed me to sort by neighbourhood, and to check off as I went. I also accounted for which experiences would be the first to be sacrificed if something didn't go as scheduled, a change of plans occurred, or our feet were in too much pain to carry on (true story, that brought Sunday's over-ambitious plans grinding to a halt).

I gave myself reasonable spans between things that were booked and prepaid (or carried penalties for missing, like dinner reservations) and filled those spans with more as-it-comes options. And I had options galore. My spreadsheet aligned with my Google Map wth flags aplenty for every neighbourhood, in case we wanted a drink, a snack, or somewhere to sit down. 

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I used a spreadsheet to list and then sort my NYC to-do list, which allowed me to group my activities by neighbourhood and keep track of all our options. Lindsay William-Ross/V.I.A.

In the end, we managed to experience a great deal of New York (primarily Manhattan) and tick off several bucket list and/or niche destinations, from the incredible three-storey immersive Summit One to some special retailers.

What to do in New York City: How to make the most of sightseeing

I can't pretend for a minute that we share all the same interests, so unless you are a former New Yorker who loves food and transit history travelling with a kid who loves Lego, ice cream, and video games, my exact itinerary is probably not for you. (But if that does describe you, let's be friends!)

One tip for visitors is to get a CityPass for major attractions; for NYC, the pass will cover your admission to the  Empire State Building Observatory and American Museum of Natural History as well as your choice of three more attractions, including Top of the Rock, the 9/11 Memorial and Museum, and the Guggenheim. You can also choose the popular Circle Line boat tours as one of your three attractions. I've also used the CityPass in Atlanta and found it's a great value for sightseeing.

Torn between Top of the Rock or the Empire State Building? Both are spectacular, but I'm going to give the advantage to Top of the Rock, thanks to the fact that you can see the Empire State Building from its south-facing viewing decks (and they have a couple of novelty experiences, including the "Beam" and the 360 "Skylift"). 

There is a museum for pretty much everything in New York, from mathematics to sex.

A money-saving tip is to find out when some museums offer free or pay-what-you-wish admission, including the Guggenheim, The Whitney, MoMA, and several more.

There are plenty of things to do for free in New York, the first of which is simply walking around. You can stand on the steps in the middle of Times Square, walk through Central Park, and walk the High Line for free. It's also free to gawk at the stunning restored ceiling of Grand Central; be sure to look for the tiny patch of black that represents what the ceiling used to look like after years of pollution and smoke stained the gorgeous artwork. 

If you are looking to load your itinerary with free things to do in NYC, there are tons of resources online to help guide you, like this often-updated Time Out roundup, or tips from I Love NY

Here are some places I visited on this trip to NYC:

📍 Museum of Ice Cream: What began as a pop-up in NY in 2016 is now a multi-city destination. The Soho flagship features a giant slide, a sprinkle "pool" you can jump in, unlimited ice cream and treats as you go, and lots of hands-on activities for kids (and adults).

📍 Soho: One of the city's top shopping districts has big brands and boutiques. I love Housing Works and New York or Nowhere (in neighbouring Nolita).

📍 Top of the Rock at Rockefeller Plaza: Journey to the top of the iconic building that's home to SNL, The Tonight Show, and entertainment history, Drink in stunning views of the city on the observation decks, relax in the indoor-outdoor cafe, and then roam the Plaza. In the winter it's where you'll see the skating rink and Christmas tree, and all year it's where they film the Today show and where you can find lots of shops and cafes, as well as gorgeous public art. 

📍 Shopping in Midtown: Between Radio City Music Hall on 6th (Avenue of the Americas) and 5th Avenue are several major stores. TV fans may wish to pop into the NBC store, and gamers will love the only North American official Nintendo Store (San Francisco will open in 2025). This is where you will also find FAO Schwarz (the relocated beloved toy store) which houses the adorable Jellycat Diner experience.

📍 Summit One Vanderbilt: Summit One Vanderbilt is an immersive observation deck located atop the One Vanderbilt skyscraper. The three-level venue combines panoramic views with interactive art installations, offering a unique sensory experience. Go at sunset or night for an even more exciting time (and don't skip the balloon room).

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Stunning city views with sparkling lights and landmarks like the Empire State Building as seen from one of the three observation levels part of the immersive Summit One Vanderbilt experience. Lindsay William-Ross/V.I.A.

📍 New York Transit Museum: Located in a decommissioned subway station in Brooklyn, this is a must-see for transit enthusiasts. The lower level features a platform lined with actual historic transit cars, most of which you are free to roam. Transit fans may also wish to do a little research on some hidden or "secret" old subway stops you can see around town. 

📍 West Village: Meander the criss-crossing tree-lined streets of the West Village to see some beautiful homes, cafés and restaurants, and boutique shops. Visit the Stonewall Inn State Historic Site at Christopher Park, have tea at Paquita, shop at Big Night, or wait in line for some of the best pizza in town at L'Industrie.  

📍 Central Park: No matter the time of year, a stroll through Central Park is a must. Use the Conservancy's detailed guides to plan your visit. 

📍 Roosevelt Island Tramway: Take a brief aerial tram from Manhattan alongside the Queensboro (59th Street) Bridge to picturesque Roosevelt Island. Explore the area's offerings and then hop on the tram or the subway back to Manhattan.

📍 Times Square: The dizzying hub of commerce and live theatre, the larger-than-life billboards and cacophony that is Times Square should be experienced at least once. (You don't have to stay long!) Grab a seat on the steps and watch the somewhat organized chaos unfold. If you are a night owl, consider arriving at 11:57 p.m. when all the billboards go dark and are lit until midnight with a unified work of art. Watch your belongings here and don't engage with the people in costumes unless you have cash for them. 

📍 Hudson Yards: This newer retail zone is a luxury mall with an incredible Spanish marketplace and food court on the lower level. This is where you can see the Vessel (you must pay to access the interior) and a great starting point for a walk on the High Line.

📍 The High Line, Chelsea Market: The High Line is a linear park built on a repurposed elevated rail line in Manhattan once destined for demolition. It features lush gardens, public art, and wonderful city views, making for an engaging stroll through the Meatpacking District and Chelsea on the island's west side. Hop off at Chelsea Market for a snack or meal inside the former Nabisco cookie factory now home to gourmet food shops and restaurants. If you can, venture over to Little Island to see one of New York's newest green spaces.

📍 Little Italy: Wander through the picturesque streets of New York's Italian community, which are lined with souvenir shops and restaurants. 

📍 Grand Central Terminal: This is a historic transportation hub in New York City known for its stunning Beaux-Arts architecture. Look for the celestial ceiling mural in the Main Concourse and the iconic four-faced clock atop the information booth, as well as the "Whispering Gallery," and the food market. A word of warning: There are not many places to sit down here, so don't choose this as a take-a-load-off spot unless you book a table to dine at one of its full-service restaurants or go to the waiting room for train riders.

More tips for fun things to see and do in NYC

Though I didn't do these activities this time around, many travellers may wish to know more about some of the city's top attractions and things to do.

  • See a Broadway show: Purchase tickets in advance online or set aside time to take a shot at getting same-day discounted tickets from the TKTS booth in Times Square.
  • Walk across the Brooklyn Bridge: Budget about 45 minutes for this experience and plan on not being the only person there. You may wish to also include heading to DUMBO in Brooklyn for more views of the bridge.
  • See a sporting event: Pick your team! NY is home to the Jets, Yankees, Knicks, Islanders, Mets, Rangers, Nets, and more.
  • Enjoy other live entertainment, from jazz clubs to the ballet. NYC is home to dance troupes, orchestras, concert venues, and several smaller theatres.
  • Go on a food tour: Eat your way through several New York neighbourhoods or marketplaces and take a bite of local history.
  • See the Statue of Liberty: You can do this by going to the island and visiting the monument (for a fee) or passing by it if you take the free Staten Island Ferry.
  • See the city like your favourite film and TV characters: Channel your inner Carrie Bradshaw.

Where to eat in New York City

For many whose motto is "will travel for food," taking a bite out of the Big Apple is absolute life goals. 

New York City is a reflection of global food culture and a trailblazer; not only does it have North America's most lauded chefs and restaurants that win prestigious awards and set trends, but it also has a gobsmacking amount of places to try foods from nations from every corner of the world. 

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Thai food meets diner classics at Nolita's Thai Diner, where breakfast dishes like baked eggs in kaho soi broth with roti offer an exciting twist on morning eats. Lindsay William-Ross/V.I.A.

There are dozens of iconic NYC foods, some made even more popular thanks to social media and pop culture, from bagels and schmears to pizza slices to pastrami sandwiches and street corner hot dog carts. There are three-strarred Michelin restaurants and acclaimed burger counters, viral chocolate chip cookies, and banana pudding you might wait in line for.

Given how synonymous New York is with the act of eating, from fine dining to street vendors and bodegas to speakeasies, planning where to eat while visiting the city can take a lot of thought. I've curated a separate guide for food-loving travellers bound for NYC from YVR packed with tips (and my itinerary of where I ate during my recent three-night sojourn). 

Exhausted? You're still in the planning stages. This is just training for the big event. You can do this! New York City is an absolute thrill for visitors of all kinds, and with some thoughtful planning, you can set yourself up for the trip of a lifetime. Have fun!


Thanks to FlightHub for facilitating travel to New York City from Vancouver by hosting our flights and hotel stay. We received support from NYC Tourism with a CityPass which covered the cost of our visit to the Top of the Rock. 

None of the above-mentioned experiences or meals were hosted; the entire itinerary was self-curated and paid for by the author with no prior arrangement with any business. While the CityPass was gifted, the tickets are standard issue general admission and accorded nothing beyond a regular experience; the venue (Top of the Rock) did not know we were media. 

All opinions and inclusions are those of the author and were based solely on personal experience. None of the businesses or entities featured were granted any previews of the story before publication or paid to be mentioned.