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The Big Apple, The Concrete Jungle, City of Dreams, City So Nice They Named it Twice. New York City is known by many names and has a reputation for its unique energy, historic charm, and killer bagels. This past Fall, I had the opportunity to visit for my very first time, and planning this trip was overwhelming to say the least! And that is coming from the most Type-A travel lover out there! I feel like in every friend group, everyone has their role to fulfill. Mine? Booking the hotel, making the reservations, obsessively researching those hidden gems. And this is a role that I take on willingly. I love the excitement that comes from the planning stages! Which is why, despite all my experience, it’s really saying something to admit that organizing this trip felt like a lot.
The following itinerary is pretty close to what ours actually looked like, but after having actually taken the trip, I moved a few things around to reflect what I wish we would have done each day. Each of the five days are separated by location so you can minimize travel time and really get to know each of the neighborhoods!
Day 1: Midtown Manhattan
Museum of Modern Art: This museum has multiple floors filled with tons of different styles. However, if you know you are the type of person to look at a piece of art and go: “I could do that.”, this is not the place for you. And that’s ok. It’s important to know your tastes. If that’s the case, I would recommend a different museum in the area. On the other hand, if you are more of an art aficionado and love learning the messaging behind different works, there are lots of cool pieces here!
Top of the Rock / Rockefeller Center: This is the place to go for some incredible views of the city! There are a few benches on the upper levels, so I would even recommend packing in some snacks or a book and just soaking in the views for a little while. (Additionally, a great place to people watch. Although, that is true of almost everywhere in New York.)
Times Square: There is so much to take in here! It’s crowded, loud, and chaotic, so if anyone in your group struggles with sensory overload, I would suggest making this part of your trip more of a drive by. That being said, there are always tons of street performers who are actually pretty entertaining! (So long as you accept the fact that they are absolutely trying to hustle you and enjoy the experience for what it is.)
See a Broadway Show: I grew up doing theatre, so there may be a bit of bias here, but I think that catching a Broadway show is a must-do for everyone! Even if musicals aren’t really your thing, there are lots of shows that appeal to a wide audience and the performances are just so spectacular and immersive. We saw Hamilton and it was phenomenal! If you are new to theatre and not sure what to see, I would also recommend shows like The Lion King, Aladdin, Newsies, Les Mis, Legally Blonde, Dear Evan Hansen, Hairspray, Frozen, Mean Girls, and Into the Woods.
Day 2: Central Park / Upper East Side
The Met: Without a doubt, one of my favorite experiences in NYC! This place is massive and full of so much incredible history. It’s pretty easy to get what I like to call “museum fatigue”, so we actually split up our visit through the day. We spent a few hours there in the morning, and another few hours there at night. (And can I just say? There is a uniquely magical feeling that accompanies walking around a museum at night! It’s much less crowded and just feels so much more special for reasons I seriously cannot explain.) If you do go The Met at night, be sure to pop up to their rooftop garden to check out some gorgeous skyline views!
Bike or Boat Central Park: Perhaps one of the most iconic locations in New York, Central Park lives up to the hype. It’s the kind of place you could wander for hours and still not see everything. At over 800 acres, this park is truly the heart of Manhattan. We rented bikes and did a couple laps around the park. There are wide, well-marked paths so even if you’re not a super confident biker, you don’t have to worry about weaving through the various types of traffic. We rented through Unlimited Biking, but this is a popular activity, so there are tons of companies nearby that rent out bikes! If biking isn’t really your thing, you can also rent rowboats and gondolas and take them out on the Central Park Lake. We didn’t have time to do this personally, but we rode past the water, and it looked magical! Willow trees line the bank and create the perfect ambiance for a boat day. Their rowboats hold 4 people and go for about $20/hour. You can learn more about this experience here.
Day 3: Brooklyn, Dumbo
Dumbo Street Markets: Dumbo is one of my favorite neighborhoods that we visited! It sits right at the base of the Brooklyn Bridge and is home to a wide range of unique street markets. Outside of the Winter season, Dumbo hosts the Brooklyn Flea, one of the largest flea markets in New York City. Tons of vendors line the streets every Saturday and Sunday, and it’s the perfect place to find some truly unique treasures to remember your trip by.
Empire Fulton Ferry Park: This park boasts some pretty spectacular views of the city and is also situated just under the Brooklyn Bridge. It’s a perfect place to picnic, watch the sunset, ride the carousel, and in the Summer, enjoy community activities. They frequently host outdoor movie nights or small music festivals, so be sure to check their event calendar for the dates that you’ll be visiting!
Walk or Bike Brooklyn Bridge: Of course, a day in Brooklyn isn’t complete without a trek across the Brooklyn Bridge. You can rent bikes here as well to ride across, or take it at a more leisurely pace and walk across. This is my personal preference as you can easily stop to take as many pictures as you want and take it in at a more casual pace. You’ll want to consider which direction to start at. If you come from Brooklyn, you’ll have views of Manhattan in the direction that you’re walking, and vice versa. However, if you plan to walk halfway and then back, it doesn’t really matter. The bridge is just over a mile long, for reference.
Day 4: Manhattan, Chelsea
Chelsea Market: The Chelsea Market sits inside a massive concourse, that is home to tons of unique food, shopping, and events. Be sure to check their schedule as well, as they sometimes host live music and fun classes here as well!
The Highline: This surprised me as another highlight! At about a mile and a half, this feels like one of the most unique walks in the city. An old rail line converted into a pedestrian walkway, you’re a few floors up, among some really unique architecture and tons of gorgeous landscaping.
St. Patrick’s Cathedral (Catacombs by Candlelight): We booked this tour somewhat on a whim, and while the Catacombs themselves aren’t anything to write home about, it was so cool to hear about the history from someone who knows so much. Our guide knew which famous person lived on which streets, and had countless stories about the history and culture surrounding the Cathedral and New York City in general.
Flatiron Building: I would say this stop is mostly for the pics, unless you plan on booking a tour. They have guided tours that walk you through the famous food, architecture, and history surrounding the building and it’s neighborhood. If you’re unfamiliar, the Flatiron Building it’s an inordinately thin, triangular building in the gorgeous Union Square neighborhood.
Day 5: Lower Manhattan
9/11 Museum: The most powerful museum experience I have ever had. Harrowing and humbling, but oh so worth it. You learn so much about the sacrifices of “ordinary” humans and it’s such a crucial moment in American history, but New York City in particular, and you get such a sense of the resilience of the people who have lived here forever. I cannot recommend this enough.
Battery Park: Battery Park is super close to where you’ll board the boat for Liberty and Ellis island. It’s right on the water and home to a stunning SeaGlass Carousel and other kid-friendly playscapes.
Little Italy: I would recommend Little Italy under one condition: you attend The Feast of San Gennaro! This is an annual festival hosted in the Little Italy neighborhood. We stumbled upon this while we were here and I can confidently say we ate one of our best meals here. There are tons of delicious street food options, fun parades, and a famous cannoli eating contest to behold during this time! It’s typically hosted in September, which is such a magical time to visit, as you get the warm Summer weather without the insane Summer crowds.
Statue of Liberty: I have never been someone who enjoys doing things simply because “If you go to New York, you just have to…”, but I will say that the Statue of Liberty is one slightly cliche activity that I think is worth it! Because the statue sits on an island, you get a quick boat ride included in the price of your ticket. This grants you unmatched views of the city! Liberty Island itself is beautiful. This is another place that is great to slow down at. You can sit somewhere with a great view (after scoring an ice cream cone, of course!) and just people watch. There’s so much more history surrounding the Statue of Liberty than I ever knew, and I enjoyed learning about it.
Our Favorite Bites
Anita Gelato (Manhattan, Upper East Side)
Gelateria Gentile (Manhattan / Brooklyn, multiple locations)
Veniero’s (Manhattan, East Village)
Citizens of Chelsea (Manhattan, Chelsea)
Bo’s Bagels (Manhattan, Harlem)
Los Tacos No. 1 (Manhattan, multiple locations)
Chela (Brooklyn, Park Slope)
Pietro Nolita (Manhattan, Nolita)
Kat’z Deli (Manhattan, Lower East Side)
Rubirosa (Manhattan, Nolita)
Junior’s (Manhattan / Brooklyn, multiple locations)
Sara Beth’s (Manhattan, multiple locations)
Carmine’s (Manhattan, multiple locations)
Trattoria Dell’arte (Manhattan, Midtown)
Prince St. Pizza (Manhattan, Nolita)
5 Napkin Burger (Manhattan, multiple locations)
Halal Guys (Manhattan / Brooklyn / The Bronx, multiple locations)