You can't visit New York City just once. I knew this before I even booked my trip.
"This will be my tourist-y trip," I thought to myself as I created my Google map of New York City. I was planning it with a friend of mine, who was also a first time visitor, and we both had a list of must-visit spots. Most of the greatest shows and movies were shot on the streets of New York City, so it comes as no surprise that we all have specific landmarks that we promise ourselves we will go and see one day: The Friends fountain in Central Park, Carrie Bradshaw's brownstone and those famous Sex & the City cupcakes from Magnolia bakery (I highly suggest the banana pudding instead), meeting Tom Hanks atop the Empire State Building (also accepting the fact that Tom Hanks does not come with that experience) - the list is endless, and it is nearly impossible to check it all off in one visit. As many people who have been will tell you, you shouldn't go to New York once. It's too dense, too beautiful, and there is way too much to see!
Everyone should take a minimum of 3 trips to New York throughout their lifetime... I said it! I also think that you should book one of those trips in the summer and one in the winter. Here are the 3 Types of NYC Trips you need to take:
The Tourist Trip
Be realistic: Your first trip to New York City is going to be checking out those landmarks you fantasized about ever since you saw your favourite movie. You also want to get a feel for the city and soak it all in. Map out your must-visit spots and put together an itinerary. Aside from movie references, there are just classic New York spots you'll want to see at least once in your life, such as Times Square, Central Park, Rockefeller Center and more. To be honest, a lot of these places are pricey or over-saturated with tourists, like yourself, so consider that when making your list. For example, really ask yourself how badly you need to be at the top of the Empire State Building. Weigh the pro's and con's, is it worth standing in line for a long period of time? Is that how you want to spend your money? If it's worth it for you - do it, you don't want to have any regrets when you leave, but, if you think you can live without it, skip it. It's different for everyone. A lot of the textbook tourist attractions consist of you visiting, taking a picture, looking around and admiring it for a few minutes and leaving. This is entirely personal preference. Add must-try restaurants to your map as well, like the famous Frozen Hot Chocolate at Serendipity 3, a gigantic slice of greasy NY pizza, or anything else your stomach desires. A few of my favourite Tourist recommendations: Walk the High Line to Chelsea Market, visit Ground Zero (very emotional), take a rickshaw ride through Central Park.
The New Yorker
Book your hotel in Chelsea and run around town like a New Yorker or someone who has lived there for a while. Chelsea is the perfect neighbourhood to do so because it's not quite as tourist-filled and it's where you can have a lot of fun. On this trip, you should book Sunday brunch at Bagatelle, which is essentially one big weird party/show. I love when sh*t gets weird; picture Storm Troopers and saxophone players partying together. Book a show at the Comedy Cellar, a comedy club in Manhattan where many top New York comedians perform and some famous ones got their start. Grab French Toast at Le Grain Cafe, get drinks at The Jane Hotel speakeasy, eat Babka at at Bread's Bakery near Union Square... the list is clearly endless. Also, a lot of these recommendations came from a friend living in NYC, so trust me, you're in good hands!
Cross that Bridge When You Get There
Book a trip with the sole purpose of checking out places outside of Manhattan. Dumbo and Williamsburg in Brooklyn are two amazing places you need to check out at some point - but you may not want to do so on your first trip to NYC because you want to get some of that tourist stuff out of your system. Dumbo is known for it's converted Brooklyn warehouse buildings and cobblestone streets that lead you to high-end restaurants, trendy cafes, and a thriving performance and gallery scene. On your way over to Dumbo, take one of those famous Brooklyn bridge photos. Afterwards, make your way over to Williamsburg; arguably, the hottest area to check out in New York these days. This gentrified neighbourhood is full of hipsters, repurposed factories, and plenty of buzzed-about restaurants. Williamsburg is gorgeous to mosey around because it's a very artistic part of NYC. Street art brightens the entire district from residential spots to commercial areas. On your way back to Manhattan, take the Williamsburg Bridge and snap a couple more photos!
Seasonal Tips:
A big part of the New York City experience is walking everywhere. It doesn't make sense to take an Uber or rent a car in a place with such busy streets, especially because there is something exciting to see at almost every corner you turn. This makes summer an ideal time to book one of your trips to NYC. It's a whole new experience as well. That city is always alive, but it's even more alive in the summer! Switch it up and book your trips in different seasons. However, I recommend booking your Tourist Trip in November/December, like I did, because everyone needs to experience Christmas in New York at least once in their lives - it's magical. Most of the tourist stuff is in Midtown Manhattan so you're close 5th Ave where the world's most immaculate Christmas displays dwell. Not to mention the tree in Rockefeller Center. If you haven't already guessed, my personal New York fantasy was to experience everything Kevin McCallister did in Home Alone 2, so being there at Christmas made me feel like a kid again! I even had my own little photo-shoot planned at LaGuardia, but when I got there it was fairly unrecognizable due to the construction of the airport. My heart broke a little. [Two] Turtle doves were also sold out everywhere. My heart broke again. However, there were a lot of creepy/disheveled women sauntering around Central Park. #NewBesties
