The 5 Day New York City Itinerary

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Advisor - Georgia Goddard
Curated By

Georgia Goddard

  • New York City

  • New York

  • City Travel

  • Food & Wine

  • Local Culture

  • Local Food

  • Entertainment

A low-angled shot of Central Park with tall buildings during daytime,
Curator’s statement

New York City is one of the most popular destinations in the world and is somewhere I have spent an extended period of time. Home to many iconic tourist spots, whilst these are included in this itinerary, there is much more to explore in NYC. I have curated this five-day itinerary to help you see more than just the well-known tourist spots and will help you experience some local hotspots in the big apple.

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Day 1: Ticking off the Midtown Tourist Spots

A picture of the view from the top of the rock observation desk

Begin your first morning in New York at Maman Bryant Park. This beautifully design chain cafe offers great coffee, pastries, take away sandwiches and a sit down brunch menu. After you’ve finished up there have a stroll around Bryant park and then walk west down to 42nd St to Times Square. Take some photos at the iconic photo spot and observe the hustle and bustle that accompanies it. Take a stroll north along 7th ave and 53rd St to visit MoMA. The famous art museum is host to many well-known pieces, including Then Starry Night by Van Gogh, as well as short term exhibitions that they change roughly every season.

Once finished, make your way to Joe’s Pizza on Broadway to grab an iconic New York slice. This is the best pizza in New York so be sure to make the most of it and take some good pictures. Afterwards, head to Ralph’s Coffee van outside the Rockefeller Centre. This pine green coffee van by the famous designer Ralph Lauren is a bit gimmicky, but that is what New York is all about! Now that you’re reenergized, go up to the Top of the Rock Observation Deck at the Rockefeller Centre. Here you’ll get to experience the best views over New York City, including seeing the Empire State Building from above.

Make your way back to your hotel to freshen up and change outfits for dinner at Tavern on the Green. This famous restaurant, that has featured in many films, lives up to its status. Nestled on the west side of Central Park, it is the perfect place to enjoy a relaxed meal after your first day in the city.

Day 2: Downtown Manhattan

A picture of cocktails on a white table at a rooftop bar

Wake up and get the day started by getting brunch at Good Thanks Cafe on the Lower East Side. This hipster spot offers classic modern American breakfast dishes and great coffee. I would recommend the avocado toast, or if your looking for something sweeter the acai bowel. Then hop on the J Subway Line southbound to Broad St to explore the Financial District. Walk down the infamous Wall Street and observe the fast-paced lifestyle. Make sure to visit the Fearless Girl and Charging Bull statues in the area. A short walk away is The Battery, a great park that has views over the Hudson and the Statue of Liberty.

Later on in the day, walk to World Trade Centre and grab a bagel from Black Seed Bagels. You can either eat in or grab and go if you wish. Once you’ve finished lunch, walk over to the 9/11 Memorial. This poignant tribute to the tragic event is quiet and you should take some time to reflect in the quiet. Visit the museum as well that showcases various stories from the historic event. It is an emotional experience, but one that you should do if in New York. End your time there by looking at the new One World Trade Centre building, a symbol of positivity and strength.

In the evening, head to the Loopy Doopy Rooftop Bar inside the Conrad Downtown Hotel. This innovative bar offers what they call ‘Poptails’, which entails an alcoholic ice pop placed inside a sparkling beverage. As well as this, it has brilliant views over the Hudson River and some excellent small plates that you can order.

Day 3: Brooklyn and SoHo

A row of tall buildings

Get up bright and early and make your way across the East River to Brooklyn for sunrise. Get an iconic yellow taxi across the Brooklyn Bridge and take in the morning scenery. Once over the other side, head towards Dumbo to see the sunrise over Manhattan. Be sure to go to Washington St to see the Dumbo-Manhattan Bridge viewpoint that is a popular photo spot. Once you’ve finished up there, get on the East River Ferry, scheduled roughly every 30 minutes, from Dumbo to North Williamsburg. This is a great way to see the area and get to your next destination! Next, walk to Jack’s Wife Freida for some brunch.

Later on, explore Williamsburg and visit some thrift stores as some of the best in New York are located here, such as Beacon’s Closet and Mother of Junk. Afterwards, make your way back to Manhattan by taking the J Subway Line to Delancy St. This subway ride travels over the Williamsburg Bridge and offers up some great views. Now that you have arrived in SoHo, take advantage of the extensive shops located here. As you’ll also see, SoHo is home to stunning architecture, so get some good pictures here.

Grab some dinner in the area at Cipriani’s. This popular Italian restaurant serves classic dishes in a relaxed setting. Once you’ve finished here, take a 10-minute walk to Mr. Purple, a rooftop bar in the Lower East Side. Enjoy some cocktails whilst taking in views of the New York skyline.

Day 4: Upper East Side and The Met

A picture taken inside a restaurant decorated with different flowers and lights.

One of my favorite things to do in New York is take a SoulCycle class. So, on your fourth day, head to the Upper East Side and take a morning SoulCycle class. They have a variety of classes with different themes so be sure to research which one is best for you. After class, take a 10 minute walk down 2nd Ave to Playa Bowls. This healthy food spot offers a wide variety of acai bowl flavors, as well as a great sweet cream cold brew.

Nearby is The Metropolitan Museum of Art, more commonly known as ‘The Met’. It is the largest art museum in the USA, so be sure to set aside a good few hours to explore and make most of the most of what is on display. After you’re satisfied you’ve seen all you want, make your way to *Central Park*. This green oasis in the concrete jungle is full of life and different sections. Make sure to see Bethesda Terrace and The Pond, which are some famous spots inside the park.

In the evening, make your way to the West Village and get some dinner at Sveta, a flowery designed Ukrainian restaurant. Its menu offers some traditional European dishes, as well as some extravagant cocktails. After dinner, make your way to Ploume for some drinks. This underground venue is a social place with great music where you can enjoy New York nightlife.

Day 5: West Village, Chelsea and Hudson Yards

A picture of the street of West Village during the daytime.

Begin your final day in the city at The Butchers Daughter, a popular vegetarian restaurant in the West Village. After a relaxing brunch, wonder around the charming neighborhood, which is home to Cornelia Street, made famous by the famous Taylor Swift song, and the apartment building featured on the hit TV show Friends. Continue walking north to the Little Island Park on the Hudson. This manmade feature is a lovely green space with views over New Jersey.

Later on, make your way to Chelsea Market. Home to many different food stalls, here you can grab some coffee and a snack. Nearby is the High Line, a public park built on a historic railway line. It's quiet environment is an escape from the bustling city below, so be sure soak in the surroundings. At the end of line, you’ll end up in the new neighborhood that is Hudson Yards. Walk around the area and see The Vessel, the areas main attraction.

As the sun starts to set, visit the Edge Observation Desk, one of New York’s newest viewpoints. It gets its name as it is a triangular peninsula built more than 1,100 feet up. Not only do the glass walls allow you to view the skyline unobstructed, but it also has a glass floor where you can see 100 stories below, which is certainly not for the faint hearted! After sunset, make your way down into the shopping center and get some dinner at Mercado Little Spain. It is comprised of various stalls that offer different dishes from all over Spain. Get a table and order multiple plates to experience all that this unique market offers.

Advisor - Georgia Goddard

Travel Advisor

Georgia Goddard

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Looking for more travel inspiration? Check out my guide, The Perfect 3 Day Itinerary for Your First Time in London. This itinerary is part of our ongoing series on travel to New York City.