New York City | 5-day Itinerary

If you’re feeling overwhelmed with choosing what to do in New York City, this itinerary is perfect! It includes a mix of sightseeing, discovering food, and the classic New York City experience.

New York City is the most populous city in the United States and the most photographed city in the world. It is known for its Lower Manhattan skyline, Central Park (most filmed location in the world), the Brooklyn Bridge (opened in 1883), Times Square, the Statue of Liberty (a gift from France), the United Nations headquarters and Coney Island’s boardwalk, to name a few. If you’re interested in commerce, entertainment, research, technology, education, politics, tourism, art, fashion, sports or photography, you’ve probably heard of it.

Being the most populous city in the states means there is a never ending list of things to do, see and eat. With other 80 museums, almost 27,000 restaurants, 783.8 km² and over 8 million people, it really is the city that never sleeps! You can definitely see New York City in 1 or 2 days but I would recommend spending at least 5 days in the city and even that won’t be enough. There is an endless number of things to do in NYC. You’ll want to come back again and again to enjoy everything the city has to offer.

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Where to Stay in New York City

The best neighbourhoods in New York City to sleep in are plentiful. Where to stay may be highly dependent on what you want to do and the vibe you want. You can’t go wrong with staying in Midtown Manhattan and walking or taking the subway to different districts. Chelsea is a very trendy neighbourhood and is packed with little eateries and easy access to the Highline. Greenwich Village has movie-set vibes and is a perfect location for a more easy-going trip. Stay in New Jersey and take the train across the river if you’re trying to visit on a budget.

TIP: If you’re looking to do any early morning photoshoots, plan to book your accommodations near your photoshoot locations like Central Park, Brooklyn Bridge, Rockefeller Centre or the Flatiron Building so you can sleep in a little. You’ll thank yourself later.

Transportation and City Pass in NYC

While the subway system is awesome and takes you to all the best neighbourhoods in the city, NYC is definitely best explored on foot. Make sure to wear comfortable walking shoes.

If you’re flying to NYC, the cheapest option to get to Manhattan from JFK is to take the AirTrain. It’s about 1 to 1.5 hours to Manhattan (depending on your mode of transportation). You can take a taxi to/from the airport (but be mindful of rush hour traffic). This may be the most economical for groups. If you fly into Newark, you can hop on the AirTrain to Newark Penn Station and take the train. This is the fastest economical option. Another option is to take a taxi (more expensive) or the bus (longer but cheaper).

As is usually the case, the NYC Pass is worth the splurge if you’re interested in at least three top attractions in the city.

What to Eat in New York City

With a 5-day New York City itinerary, you’ll have to make the decision if you’re going to eat out. There is an almost endless number of possibilities for food in New York City and any style of cuisine! The best deal you can ask for is a dollar slice of pizza. Check out 99¢ Fresh Pizza for the most consistent slices in the city. New York Cheesecake at Junior’s is the best in town. Another classic is a Black and White cookie from Zabar’s. Magnolia Bakery cupcakes were made famous from Sex & the City but I’ve heard their banana pudding is better. The best sushi I have ever had was at Hatsuhana Sushi. The Oyster Bar Restaurant in Grand Central Station is a vibe in and of itself!

Included in the post are also restaurants based on the itinerary/location in the day. You really can’t go wrong with anything on this list!

New York City 5-day Suggested Itinerary

Grand Central Terminal/Oyster Bar Restaurant and Times Square

Start your day at Grand Central Terminal. It is a world famous landmark in New York City that is more than just a terminal. Not to be mixed up with the Grand Central Station (a post office down the street), Grand Central has retail, dining and is an iconic tourist attraction.

Oyster Bar is the oldest restaurant in Grand Central Terminal and reservations are recommended. If you don’t like oysters, they have a selection of seafood specialties. (NOTE: it is temporarily closed due to COVID-19).

Times Square is a must visit for a first timer but tourists beware: it is definitely a tourist trap! Watch out for costumed characters (you have to pay for a picture with Elmo), caricature drawings, ticket scalpers and chain restaurants (not really a scam but spend your money on better food elsewhere in the city). Take in the lights and the hustle and bustle of the area. It’s almost always busy and if you’re looking for smaller crowds go late at night or early in the morning.

Natural History Museum, Central Park, MET, Comedy Cellar

Spend your second day in Manhattan. Start your day with brunch at the Milling Room or Good Enough to Eat. Next, head to the Natural History Museum. With over 80 museums in NYC, this one should be at the top of your list. Admission is “pay what you can” with a recommended amount and you can pay one fee for a group. There are over 34 million specimens in the museum. NOTE: You currently have to book a timed slot online due to COVID-19.

Central Park: The Natural History Museum is across the street from Central Park. Central Park is NYC’s iconic 843-acre park and the most visited urban park in America. You can visit the Belvedere Castle, Central Park Zoo, Strawberry Fields (memorial to John Lennon, who was murdered just off the west side of the park), Bethesda Fountain and Terrace, Conservatory Garden, Loeb Boathouse on The Lake (you can rent a boat and paddle around the lake), The Mall and Literary Walk, Central Park Carousel and Conservatory Water. In the winter you can go ice-skating on the Wollman Rink or Lasker Rink. In the spring, you can enjoy the cherry blossoms. You could honestly spend an entire day enjoy all the park has to offer! This itinerary is jam packed so enjoy a New York Hot Dog and ice cream before heading to the MET.

Metropolitan Museum of Art (MET): The MET houses an incredible display of art spanning over 6,000 years and is the largest art museum in the United States. Admission is also “pay what you can”. It is another location you could spend all day at or dedicate a few hours to wander through.

West Village and Greenwich Village: The best Italian food in the West Village is I Sodi, where you can have dinner before heading to Smalls Jazz Club in Greenwich Village. SmallsLIVE Foundation is a not-for-profit arts organization. Book tickets at the Smalls Jazz Club in advance or get their walk-in special ($25) if there’s space. Next, head to the Comedy Cellar at the Village Underground location. This is where now-famous comedians started out including Ray Romano, Dane Cook and Jerry Seinfeld. Be prepared for a deep belly laugh of a night! There is a two item minimum per person (drinks and/or food), reservations are a must, no cameras during the show and the house is always packed! If you’re still feeling like living up the NYC nightlife, stop by Fat Black Pussycat for a night cap. It is next door to the Comedy Cellar.

Meatpacking District and Soho

Start your day by walking the High Line. It is a park built on the disused southern portion of the West Side Line (old raised train tracks). Get off at the Chelsea Market: a food and retail hub in the heart of the Meatpacking District. There’s something for everyone here: art, food, museums, flea markets, you name it! For a decadent and Instagram worthy milkshake, stop at Black Tap (the milkshakes are way better than their burgers).

Spend the afternoon shopping on Bleecker Street: an east–west street in Manhattan and also known as the Greenwich Village nightclub district.

End the day on a rooftop patio with amazing views of Central Park and New York City at Viceroy.

Brooklyn Bridge, SoHo, Laduree, Battery Park and 9/11 Memorial, Monarch

Start the day off by taking the subway to Dumbo, Brooklyn. Make sure to stop on Washington Street for a classic view of the Brooklyn Bridge. Also check out the Brooklyn Bridge Park. You’ll find the Empire Fulton Ferry, Fulton Ferry Landing, Greenway, John Street, Main Street, many gardens, and six action-packed piers in Brooklyn Bridge Park. If you want some photos with small crowds on Brooklyn Bridge, head there early in the morning (6 am). Stop for breakfast or brunch at the Time Out Market in Brooklyn which boasts 21 eateries and 3 bars. You could spend an entire day in Brooklyn, but this itinerary takes you back for a walk across Brooklyn Bridge to SoHo.

Walk the Brooklyn Bridge (45 minutes) to SoHo for designer boutiques, fancy chain stores and high-end art galleries. I particularly love window shopping at the Ted Baker store. Dash is the well known boutique started by the Kardashian sisters.

You’ll want to stop at Ladurée in SoHo for lunch: it is the famous tea shop and restaurant in Paris. The SoHo location has a beautiful hidden garden outdoor patio and an amazing menu that you’ll be sure to enjoy.

Next, head to Battery Park and the 9/11 Memorial and Museum to take a minute to reflect on the tragedy of 2001. The 9/11 Memorial is free and open to the public seven days a week, 10 a.m.–5 p.m. Museum tickets can be purchased and I highly recommend a visit if you have some time.

Finally, spend the evening at Monarch: a rooftop bar with an amazing view of the Empire State Building.

Rockefeller Centre, 5th Avenue Shopping, Hatsuhana Sushi, Broadway

The final day in this New York City itinerary offers more iconic experiences. Have an early brunch at a delightful restaurant called Penelope followed by views of the city from the Top of the Rock. I recommended the Top of the Rock rather than going up the Empire State Building. You get a great view of the Empire State Building AND the same view of the city. You can book reservations online.

Next, spend some time on 5th Avenue exploring the shops and picking up a few souvenirs. If you’ve done too much walking in the last few days, take a break in Central Park by working your arms and resting your legs in a canoe on the lake.

You’ll need to make reservations at Hatsuhana Sushi for dinner: and if you go to any restaurant in NYC you have to go to this one. The food is so fresh and the sushi rolls are melt-in-your-mouth amazing.

Spend your last evening going to a show on Broadway. Some tips for getting cheap broadway tickets:
1. Wait in line on the day of the show at TDF’s TKTS Booth under the red steps in Duffy Square (47th Street and Broadway) where you can get tickets 50% off
2. Rush tickets: go to the Box Office when it opens (10 am most days or 11 am Sundays) or enter an in-person lottery (for popular shows like Wicked) or online lottery through TodayTix).

BONUS: Christmas in New York City

Christmas time is a wonderful time of year to visit New York City. The city and businesses spare no expense in making this one of the top Christmas destinations in the world. It truly is magical!