New York City: A 5-Day Guide for First-Time Visitors

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Advisor - Chanda Daly
Curated By

Chanda Daly

  • New York City

  • Arts & Culture

  • City Travel

  • Luxury Travel

  • Guided Tours

  • Entertainment

  • Hidden Gems

New York City skyline from Brooklyn.
Curator’s statement

New York City is undeniably one of the most exhilarating cities in the world. As a first-time visitor, it's natural to feel compelled to explore its iconic and renowned attractions. However, even after numerous visits, the city continues to offer a wealth of experiences that would take a lifetime to fully embrace. Therefore, it is recommended to begin your initial trip to New York by visiting the top attractions, ensuring that you immerse yourself in the city's vibrant energy and must-see landmarks. This way, you can lay a solid foundation for future visits, allowing you to delve deeper into the countless hidden gems and lesser-known treasures that the city has to offer.

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Day 1: Arrival day

230 Fifth rooftop bar and panoramic views.

You can easily access a Taxi, Uber or Lyft outside of the airport. After settling into you hotel, consider beginning your New York City experience by heading to a rooftop bar for an unforgettable dinner and drinks. From this elevated vantage point, you can witness the mesmerizing cityscape illuminated by dazzling lights, creating a breathtaking view that captures the essence of the city's vibrant ambiance. 230-Fifth stands out as one of my preferred rooftop bars and it holds the distinction of being the largest rooftop bar in Manhattan. The unparalleled views it offers include a stunning perspective of the iconic Empire State Building, as well as panoramic vistas of the cityscape from its expansive, wrap-around deck.

Day 2: Lower Manhattan

Restaurant with medals in NYC.

Dedicate your day to exploring Lower Manhattan, a significant and emotionally profound experience. While it can be challenging to endure, it is recommended for everyone to visit the 9/11 Memorial and Museum. Both sites offer opportunities to spend hours or most of the day, reflecting on the somber events and paying respects to those who tragically lost their lives. It serves as a poignant reminder to never forget the profound impact of that day and the importance of honoring the memory of those affected by the events of 9/11.

Situated just a block away from the former site of the Twin Towers, O'Hara's Restaurant and Pub holds a significant location for visitors to the Memorial. The establishment's proximity to Ground Zero is fitting, making it an ideal spot for lunch before or after paying respects at the Memorial. During the tragic events of the towers' collapse, the pub's windows were shattered, leading to a closure of seven months. However, upon reopening, it took on a new purpose, becoming a cherished dining destination for the workers who tirelessly toiled at Ground Zero. Today, O'Hara's stands as a powerful monument in its own right, adorned with badges contributed by firefighters, police officers and recovery workers from across the United States, serving as a solemn tribute to those who bravely served and tragically perished that day.

Make your way to St. Paul's Chapel, the oldest surviving church in Manhattan, which offered rest and refuge to recovery workers at the WTC site after 9/11.

Day 3: Walking tour & Museum of Natural History

Museum of Natural History in New York.

Take a private or small group walking tour of Manhattan. This is the best way to see most of the boroughs, hear fun tidbits about the famous living there and movies filmed in locations as well as a rich history of the beginnings and changes of Manhattan over time. Your guide will effortlessly guide you through the various areas by subway and walking. It is a nice retreat from trying to figure out where to go and how to get there on your own. We saw and learned so much in four hours!

Later that day, you can head to the Natural History Museum for a few hours to top off the day. There are dining options for dinner inside the museum as well so you can fit it all in.

Day 4: Central Park & Times Square

View from a lounge in Times Square with food and a glass of wine.

A visit to Central Park is an essential part of any trip, offering a sprawling expanse of 843 acres within the concrete jungle. This magnificent park has served as a backdrop for numerous movies, and with proper planning, you can visit the specific filming locations. To ensure you can explore the entire park, consider renting scooters, bikes, or razors, or opt for a charming horse-drawn carriage ride. Don't forget to make a stop at the renowned Tavern on the Green—an experience everyone should have at least once. To fully enjoy the ambiance, request an outdoor patio table where you can bask in the beauty of the surrounding trees and revel in the fresh air. Keep in mind that Tavern on the Green tends to book up quickly, so it's advisable to make a reservation 60 days in advance if possible. Immerse yourself in the vibrant atmosphere of Times Square during the evening, starting with dinner with captivating views.

Consider visiting The Broadway Lounge located within the Marriott Marquis Times Square. This popular venue offers stunning views of the lit-up billboards and is ideally situated close to the Broadway theaters. Close the evening by seeing a play on Broadway.

Day 5: Brooklyn

A woman on the Brooklyn Bridge.

Spend a Saturday or Sunday in Brooklyn. I recommend starting your day in Brooklyn, then ending your day walking the Brooklyn Bridge back to Manhattan at sunset for the most stunning views of the city. Start with lunch at the famous NY pizza at Grimaldi's in Brooklyn. After lunch, walk to DUMBO to the Brooklyn Flea, held Saturdays and Sundays in DUMBO from April through December. You can find unique jewelry, art, antiques and clothing in an outdoor setting.

After you belly is full and your wallet is empty, go to the waterfront for views of Manhattan. There is a carrousel by the water and a few other dining or drink options with outdoor seating to full immerse yourself in the surroundings. Be sure to head to the Brooklyn Bridge before sunset. Take your time strolling across and enjoy the mesmerizing sight of the sunset casting its warm glow over the city's majestic skyscrapers.

Advisor - Chanda Daly

Travel Advisor

Chanda Daly

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Looking for more travel inspiration? Check out my guide, 3 Days in Napa: A Journey Through Wine Country.

This guide is part of our ongoing series on travel to New York City.