Read my introduction to this series HERE. In this instalment I’ll walk you through how I usually approach the logistics of a weekend in New York City following my personal philosophy of embracing the cliché.


The Flight:

One of the best things about New York’s importance on the world stage is how many flights are available. It’s barely an hour in the air from Toronto so my husband and I like to meet at the gate after work on a Friday and fly over without taking any time off at all. I find Newark’s the easiest commute to figure out because the trains are really self-explanatory but it’s also the furthest from the city centre so, if you’ve got the cab fare, fly into JFK or Laguardia and take a car to your hotel.


The Stay: 

When I visit New York City, I tend to stay with friends rather than spend my money on a hotel. But if money is less of an object for you or you don’t have friends in the city, I do not want to see you on the subway out to Brooklyn with me. I get it, Brooklyn is cool and, if you’re looking to move to NYC, by god, yes, that’s where you should be focusing your search. But that’s not what we’re talking about. A nice park, a big library, some good restaurants- that’s your typical big city stuff. No, I want you in midtown. That’s right, midtown. It’s crowded and smelly and overpriced but it’s the area of New York that is the most distinct from everywhere else in the world.


Plus, if you’re staying in midtown, you’re going to have the easiest time navigating the gridded streets on foot or the basics of the central subway map. It’s a very user-un-friendly subway system with trains arriving on different tracks and occasionally flipping to express just to throw you off so, the closer you are to everything, the better (one saving grace: there’s decent cell service in the subway system so your maps app should work fine).


When not on a budget, I’m a big fan of choosing a hotel that is itself a tourist attraction, or adjacent to one (in Mumbai I stretched my budget to stay at the Taj Mahal Palace and every second was an experience without even going outside). If you’re really a high roller (and reading this in the post-renovation future), the Waldorf’s really where it’s at in New York for luxury and history in a prime location. But the Hyatt at (which means “near”) Grand Central is a decent compromise that tours you past major landmarks every night on your freeingly simple walk home. The best bang for your buck in midtown is the Pod hotel, which has a kind of modern, elevated hostel vibe but is reliable, clean, well located, and (relatively) affordable. I use ExpediaForTD for all my bookings but my friend who does a lot of random weekends in New York swears by the Hotel Tonight app if you’re looking for last minute deals.


What to Bring: 

There are only two things you 100% absolutely need when visiting New York: a smartphone with data and good walking shoes. Because it’s one of very few cities where it’s actually slower taking a car, the ability to navigate yourself around the the city is the key to enjoying yourself. I’m also of the opinion that New York’s most iconic feature is its construction and atmosphere more than any one singular attraction so the walk from place to place is the activity itself. I’ll provide a full sample itinerary later in this series but, frankly, it’s mostly just wandering around. Choose outfits that can transition from day to evening so you’re not worrying about stopping back at the hotel, and don’t carry around too big of a bag (I never feel like I have enough room to maneuver in New York, don’t make it harder on yourself). But that’s it, just regular clothes, sensible shoes, and a reasonable purse is all you need packing-wise. I usually do the whole weekend with just a shoulder bag.


Weird Hyper-Specific Tip:

An annoying thing New Yorkers do is brag about the quality of their water. Bizarrely they often do this when talking about bagels or pizza crust where the difference is undetectable but I will give it to them on water quality when it comes to my hair. I’ll usually do a blow-out before a weekend trip so I don’t need to worry about re-styling but New York’s soft water does wonders for the curls so don’t be afraid of the air dry.


Bonus Anecdote:

This isn’t relevant anymore (thank god) but I came in November 2021 and January 2022 so I want to talk about how I got my PCR test to be able to fly home a few days later. New York’s free testing system was a sight to see so I’m mentioning it in this travel guide if not as a tip at least as a tip of the hat. It was simple, accessible, inclusive, efficient and probably the best thing I’ve ever seen out of New York other than Sesame Street. 1am, dead of winter, no local health coverage, we just walked up to a van in Time’s Square and were emailed results a day later that would have cost us nearly $300 anywhere else. That was a real “only in New York” thing for me- something about the specific venn diagram of the city’s population, location, politics, and resources allowed them to respond with incredible effectiveness after those same qualities put them in above average danger early on. They really took care of each other and, notably, of their tourists. I’ve never liked New York so much as I did in that mid-pandemic period when testing and vaccine checks were in place, crowds were still somewhat sparse, but care was front and centre.


Stay tuned for parts 3 & 4 of this series when I get into the real cliché goodness of how I do New York- where to eat and what to do. It’s very uncool, which is the best way to do anything.