New York In May: The Ultimate 48-Hour Itinerary!

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New York in May is a magical experience that every traveler should have at least once in their lifetime.

The city truly comes alive during this month, as the warmer weather brings out the best in New Yorkers and visitors alike.

There is something about wandering through the streets of New York City, surrounded by towering skyscrapers and the constant buzz of activity, that is simply unforgettable.

If you’re planning your first visit to the city and wondering where to start, we’ve got you covered.

Read more below as we’ve compiled a list of iconic places that you simply can’t miss during your two-day trip to NYC. From the breathtaking views of the Empire State Building to the lush greenery of Central Park, you will journey through the very best of New York City.

So, put on your walking shoes and get ready to discover the Big Apple like never before!

New york in may
Plan an 2-day trip to New York in May!

CONTENTS – In this article, you will discover the best places to visit in New York City in May, including:

Two Day Itinerary to Get the Best of New York City

There is something magical about wandering through New York City, amidst the insane skyscrapers.

This city has a lot to offer. But with only 48 hours to explore, you’ll want to visit some iconic places in New York – especially if this is your first visit to “The Big Apple.”

Below, you’ll find several places that you should include in your 2-day trip to New York in May.

Day 1 of New York in May Itinerary

Let’s hit some of the most iconic stops in New York City first. This will be a busy itinerary, but you will feel like you’ve seen a lot in a short time.

Empire State Building

Empire State Building, New York
Visit the iconic Empire State Building when you’re in NYC.

The Empire State Building is an iconic building (probably across the globe) and every architect’s inspiration. The building came alive in the year 1931 and was one of the tallest buildings of its time, for many years.

You can visit one of the two observation decks and get a bird’s eye view of the whole city of Manhattan.

You can even check out the dine-in places that are housed inside the building.

While you’re inside, you’ll find some great places for a selfie, like standing along side a large replica of the building, and posed within King Kong’s large ape hand!

Rockefeller Center

Rockefeller Center in NYC
The famous Rockefeller Center in NYC is a great take at any time of year.

If you are visiting NYC in winter, then paying a visit to Rockefeller Center is a must. It comes alive during winter, because of its outdoor ice-skating ring and Christmas tree.

But it’s a great destination to visit at any time of year.

While you are here, you should check out the NBC Studio. Just be sure to book your tickets in advance!

The must-visit spot at this center is its observation desk. People call it ‘The Top of the Rock.”

Times Square

Times Square in New York City
Times Square is the hustling, bustling heart of New York City.

Times Square is a known business hub across the globe and various brands aspire to have their neon sign board flashing at this very location.

Some common sights in this area are flashy neon signboards, QSR chains (Subways, Burger King, etc.), and street hawkers. You’ll also recognize it as the place where the famous “ball drop” takes place on New Year’s Eve!

Visit Times Square at night when you visit New York in May and you will know what one of the busiest streets in the world looks like!

You will also come across a lot of Broadway theaters. There are hundreds of shows going on every single night and you can pick one to spend your evening well.

St. Patrick’s Cathedral

A trip to New York is incomplete if you haven’t visited at least one of the iconic churches in the city. The most famous one would be St. Patrick’s Cathedral.

This place is designed in a neo-gothic style and thousands of tourists from different corners of the world pay a visit to this cathedral, to bask in its beauty.

If are a fan of art (or even slightly appreciate artwork), then do not miss out on checking some important elements of the cathedral, such as the sculpture of Pieta and the detailed rose window.

In fact, St. Patrick’s Cathedral looks almost a bit out of place with its ornate architecture among sleek city skyscrapers. But that makes it all the more a point of interest!

Central Park & Bow Bridge

Imagine one of the busiest cities of the world (yes, we are talking about Manhattan) juxtaposed with a huge & peaceful park, right at the center of this hustling-bustling city.

You guessed it. This reprieve from the clamour of the city is Central Park.

No doubt that paying a visit to this park is a must!

In it, you’ll want to visit several locations that are perfect while you’re visiting New York in May. Among them are The Bethesda Terrace and Fountain, Belvedere Castle, and the model sailboats.

You can even take a horse-drawn carriage ride through this expansive green space.

If you’d like to take a calming walk inside the garden, then you can check out the Bow Bridge. It’s one of the busiest spots within the park, but still worth visiting. Many lovers choose this bridge as a spot for their perfect marriage proposal!

Grand Central Terminal

Grand Central Terminal in New York City
Grand Central Terminal has a rich history.

Part of what makes Grand Central Station so iconic is its architecture. It’s a very good reason for you to pay a visit to this place.

Do not ride (unless you want to). Just visit the terminal and bask in the beauty of it.

You will find teal murals of constellations across the ceiling, so don’t forget to gaze up! And, if you are hungry, you’ll find a diverse food court with tasty treats and drinks beneath the station.

You can even visit Grand Central Station to explore outside the city limits areas – which of course, it what it was designed for.

Day-2: New York City in May

One the second day of your New York in May itinerary, you’ll visit the remainder of the most important sites in the city. Let’s go!

Ellis Island

You’ll find Liberty Island and Ellis Island side-by-side, so it makes sense to combine these two attractions into a single visit. You can buy a combo ticket to see these two treasures in one trip.

You can also get this useful pass to check out New York and save some cash.

Ellis Island was an immigration station from 1892 to 1924. Here, they processed over 12 million immigrants to the United States!

The building was abandoned for a long time (almost 30 years) and has been restored. So, you can now check out the museum of this island and also the writings on the 100-year-old walls, stating the history of this island.

The Brooklyn Bridge

Walking across the Brooklyn Bridge is a must-do experience when you visit NYC!

Take a stroll in the evening and check out the whole of the Manhattan skyline that is clearly visible from this bridge. You’ll also see the Statue of Liberty off in the distance.

Not only will you cross this iconic landmark on foot, but you will see plenty of souvenir vendors along the way. Admittedly, this might not be the cheapest place to buy a souvenir, but it might be the right time to select a remembrance of your visit!

You will simply love this experience.

And if you are not a fan of the Manhattan skyline, you can skip the skyline and check out the scenic roadways around NYC.

Statue of Liberty

The Statue of Liberty in New York City
What could be more iconic than the Statue of Liberty?

If we talk about an iconic building that is recognizable across the world, then that building will have to be the Statue of Liberty. The mighty neoclassical sculpture is housed on Liberty Island, in New York City.

The Statue of Liberty is a national treasure for the USA, gifted to America in 1885 by the French. It signified the two countries alliance during the Revolutionary War.

Today, millions from different parts of the world come here to cherish the beauty of this sculpture.

That’s because it is not just a sculpture – rather it’s a symbol of freedom.

If you want to go up to the top, you’ll want to get tickets ahead of time. And if you want to just cruise by the statue, take a ride on the Staten Island Ferry. This free service between Manhattan and Staten Island passes directly by Lady Liberty. 

Final Thoughts on New York in May

After a whirlwind 48 hours exploring the vibrant city of New York, you’ll be left with memories that will last a lifetime.

From the bustling streets of Times Square to the peaceful oasis of Central Park, there’s truly something for everyone in this incredible city.

We hope our itinerary has helped you make the most of your visit to New York in May. But, of course, this is just the tip of the iceberg when it comes to all the amazing things to see and do in the Big Apple.

So, whether you’re planning a return trip or simply dreaming of your next adventure, remember that New York City is always ready to welcome you back with open arms.

Where to Stay in New York City


Jackie Gately at the beach


About Jackie Gately, editor-IN-CHIEF

I'm Jackie Gately, your travel confidante and the creative force behind Enjoy Travel Life, awarded the "Best Casual-Luxury Lifestyle Blog (USA)" in Travel and Tourism by LUXlife Magazine for four consecutive years.

With 25 years of published expertise, I'm a seasoned writer, editor, and photographer curating inspiring travel guides and lifestyle tips for empty nesters. I hope to kindle your spirit of exploration, encouraging you to overcome obstacles and turn your dreams into reality.

Learn to minimize your pre-travel angst and maximize the joy of exploration with insights from my experiences. Let's make every adventure a celebration of this exciting phase of life! 

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