Planning a NYC Trip: Top Tips and Tricks

Are you planning a nyc trip? Read our guide to planning the best possible trip to the Big Apple, so that you get the most bang for your buck.

60 million people visit New York City annually. Want to know why?

New York is the city of dreams, hope, and hustle. Television and popular culture have romanticized this city beyond compare, leading it to become one of the most sought-after destinations in the world.

Is visiting NYC worth it? Absolutely.

The city, which is home to over 8.5 million people, is bursting at the seams with things to do, places to go, and sights to see. Planning a NYC trip can seem overwhelming.

What do you prioritize on a short trip? What is important to see?

Begin by resigning yourself to the fact that it will be impossible to scratch the surface of NYC in just one visit. The silver lining is that you’ll have to plan a second trip just so you can take it all in again.

Read on for your essential guide to NYC: what to see, what to avoid, and all the tips and tricks in-between.

When to Visit?

The best time to visit NYC depends entirely on the kinds of activities you want to take part in. While the city is an evergreen location, each season has its advantages and disadvantages.


An essential New York itinerary during this season must include a free performance and picnic in the park. Enjoy the green spaces and take in the sights of the river.

There are many outdoor festivals this time of year such as the World Pride Celebration and Museum Mile Festival. Visiting in the summer is the best time to get the quintessential NY experience.


This is a special time in the city as it is the perfect weather (not too hot, not too cold) for walking around and taking the city in. The Broadway season, Oktoberfest, and the Macy’s Thanksgiving Day parade are all sights not to be missed. This is a great time to visit if you want to avoid too many tourists and enjoy great deals on food and drinks.


The colder months can be a magical time to visit New York. You’re able to enjoy the shopping season surrounded by twinkling lights and lots of Christmas cheer. Check out the iconic Rockefeller Centre tree lighting and ice skating, or warm-up for some hot cocoa before the Times Square New Year’s Eve ball drop.

However, if you’re looking for a quiet time, the winter season is probably not for you as it is New York at its most crowded.


This time of year the city’s bursting with flowers, trees, and beauty. The Yankees and Mets have season openers while rooftop bars across the city start opening up as the winter thaws. Hit the Tribeca Film Festival or catch the beautiful Cherry Blossom Festival at the Brooklyn Botanical Garden for a great experience of the city.

Ultimately, there is no ‘best’ season to visit the city. Just take a look at your New York itinerary – is there a particular time of year all the events you’re interested in take place?

If yes, pick that season to visit. If not, pick any time of year that’s convenient to you- you’ll still have an amazing experience, we promise.

Where to Stay and What to Do

Forget the seven boroughs. NYC has dozens of neighborhoods with thousands of options for hotels and Airbnb. Don’t get overwhelmed, just narrow it down starting by the neighborhood that works best for you. From there, it’s as simple as booking a rental or hotel.

If you’re unsure how to go about planning your stay, Westgate NYC – Specials has a great guide on picking out a hotel in a vibrant and interesting neighborhood.

Each neighborhood in the city comes with a different cultural past with unique activities and things to do. Here are some of the best neighborhoods for visitors to stay in when they visit the city.


The financial district is where New York City as we know it today was born. Full of colonial architecture, museums, and historic sites, this neighborhood is ideal for those who want to take in the culture. You’ll find great restaurant options, but not much evening entertainment like shows or clubs.

Must see: Wall Street, 9/11 Memorial, and Museum, The Museum of Jewish Heritage.

Chinatown and Little Italy

New York is one of the most diverse and multicultural cities in the world. When planning a trip to NYC, Chinatown is a definite must-do. Authentic restaurants, shows, and atmosphere make this neighborhood essential.

Little Italy, on the other hand, is mostly just a tourist trap and much declined from its historic past. You won’t find authentic Italian food or real Italian-Americans living here anymore. Our suggestion is to skip Little Italy and enjoy the atmosphere of Chinatown instead.

Must see: Mulberry Street, street art, food carts.

TriBeCa, Nolita, and SoHo

Some of the most fashionable neighborhoods in all of NYC, this trifecta is a must-stay for anyone interested in fashion, art, and design. Many of its old buildings were former factories, but the industrial area has developed to house chic spas, boutiques, and restaurants.

It’s also the best neighborhood to patron local designers, and visit innovative bars, clubs, and theatres.

Must see: Museum of Contemporary art, local galleries, architecture, celebrity sightings.

Lower East Side and the East Village

Both these neighborhoods are young, fun, and filled to the brim with avant-garde experiences. Definitely one of the most vibrant areas in Manhattan, you’ll find up-and-coming artists, chefs, and designers opening boutique stores and experiences here. The neighborhoods are also known for their bars, clubs, and lounges.

Avoid this area if you’re traveling as a family as it can get loud and busy at night sometimes.

Must see: Tompkins Square Park, Ukrainian Museum, nightlife.

Chelsea and the Meatpacking District

This area is extremely cultural with bars and clubs galore. The Meatpacking District was named for the slaughterhouses that used to crowd the area, but it is far from that now.

There are no schools or churches in this part of New York City, so opt out of it if that may be an issue for you.

Must see: Highline Park, nightlife.

Flatiron District, Union Square, Gramercy Park

One of the most walkable areas in the city, Gramercy Park is famous for its historic clubs and homes. You will find many an outdoor performance at Union Square, while the Flatiron District is a historic industrial landmark for the city.

Must see: Off-Broadway Shows, dining, historic sites.

Times Square and Midtown

Most visitors hit Times Square at least once on their New York itinerary, but that’s not all there is to this area. It is filled with shops, arenas, and tourist attractions.

However, it is extremely crowded and noisy, and certainly not the most authentic New york city experience.

Must see: Museum of Modern Art, Macy’s Rockefeller Centre.


This is the most populous borough of the city and boasts amazing views of Manhattan. Prospect Park is great for strolling, and the area’s classic brownstone apartments are well worth a visit. The district is also filled with artists and designers and has gained the reputation of being culturally forward and progressive.

Must see: Brooklyn Botanical Gardens, Prospect Park, Brooklyn Museum, architecture, dining.


One of the most rapidly developing neighborhoods of the city, Harlem offers visitors an authentic New York experience. It is home to beautiful brownstone-lined streets, gospel churches, and soul and Caribbean dining.

Must see: Historic homes, bars, restaurants.

Other interesting neighborhoods to stay at and explore are the Bronx, Harlem, and Murray Hill. Take day trips to these neighborhoods if you don’t have time to stay, as they are well worth the visit.

The Best-Rated Attractions

Want more New York trip ideas? This list will provide you with a run-through of all the sights to see and why they are important.

This way, it doesn’t matter whether you’re on a three-day or three-week trip to the city – you can just hit all the sights that interest you.

Here is the best New York has to offer:

  1. Statue of Liberty/ Ellis Island: Ellis Island was the landing spot for so many immigrants, so it is truly is an iconic sight. Take the ferry over to visit the Statue of Liberty, which is beautiful with amazing views of the city.
  2. Wall Street: There is heavy security in this area, but take a picture with the famous bull sculpture!
  3. Federal Hall
  4. Museum of American Fiance
  5. Trinity Church: built in the Gothic style in 1776, it is one of the oldest churches in America.
  6. World Trade Centre and 9/11 Memorial Museum: Learn about the heartbreaking event and pay tribute to the victims of the attacks here.
  7. Ellen’s Stardust Diner: This classic American Diner is special because they surprise you with performances between meals!
  8. Walk the Brooklyn Bridge: Particularly beautiful at night, you’ll see amazing views of Brooklyn and the City Hall here.
  9. Prospect Park: Spread over 500 acres, this spot is perfect for a stroll, picnic, or to catch an outdoor performance.
  10. City Hall: This is the seat of the New York City government and an architectural treasure of the city.
  11. Empire State building: Truly an icon of the city, be sure to get here early to avoid the tour groups and long lines.
  12. Grand Central Terminal: This historic train station is the perfect place to people-watch and gets a feel for the city. There are free walking tours every Wednesday so catch that if you’re interested in its history.
  13. Rockefeller Centre: Famous for ice skating and the Christmas tree, this is a must-visit during the winter season!
  14. Times Square: An absolute essential for every tourist, try to visit during the nighttime as the lights and billboards give off an electric atmosphere.
  15. See a Yankees/ Mets/ Rangers game
  16. Central Park: You could get lost walking this massive park. Hike, bike, row in the lake, or check out the zoo. Free concerts like Shakespeare in the Park during the summer make it an unbeatable spot that tourists and natives alike flock to.
  17. Metropolitan Museum of Art
  18. American Museum of Natural History
  19. The Guggenheim Museum
  20. Broadway show: New York is the theater capital of the world. Check out Wicked Dear Evan Hansen, School of Rock, or any of the countless other shows always available in the city.
  21. Museum of Modern Art
  22. High Line: This is a converted train track that is now a walking garden. It overlooks the city with plenty of public installations, food stalls, and nature to keep you occupied.

New York City’s list of attractions and sights is almost never-ending, but if you had to choose some to visit, we’d suggest these. Pack all the sights into one small trip, or leisurely spread out your sightseeing across several days for a less stressful time.

This way, you can spend a lot more of your time strolling through and taking in the city’s electric atmosphere.

Ready to Start Planning an NYC Trip?

New York City is truly one of the most magical places in the world. While planning a NYC trip may seem overwhelming, just enjoy your time and take the city as it comes.

Whether you choose to explore this city by season, neighborhood, or attraction, NYC has something for every kind of traveler.

Did you find this article useful? Check out the site for more on planning dream vacations.


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