Travel Route – Two Days in Midtown Manhattan

Where will we explore? In the heart of the heart – Midtown of New York City

What are the travel routes? A two-day travel itinerary hitting all the must-sees and dos in Midtown Manhattan

When is it best to visit? Manhattan is always buzzing, and you can do these routes year-round (preferably when it's not rainy or snowy)

Who is the trip suitable for? Couples, friends, young and old

What transportation will we use? Mostly, get those leg muscles ready (and also Metro tickets)

How intense is it? Daily tours that can also be a bit long, you can skip slightly less important places or extend the itineraries for an additional day trip.

Information about the itinerary

Midtown Manhattan is pretty much the center of the world. Manhattan is built from two main waves of skyscrapers – downtown serves as the global financial center and midtown acts as the heart of New York City. In midtown, there's a wonderful mix of corporate headquarters in iconic skyscrapers, bustling streets filled with shops, department stores, and all the fun of the shopping world. The streets are also packed with entertainment spots for day and night – restaurants, concert halls, theaters, and more.

Midtown Manhattan isn't huge, but it's extraordinarily intense. It's laid out with a series of main avenues stretching north to south, intersecting with rows of streets running east to west.

The grid layout of Midtown is crossed by the Broadway diagonal, creating central squares where it meets the avenues. Walking tours lead between the squares, taking you to all the must-see sites, towers, attractions, and shopping areas in Midtown.

Click here for all the information about public transportation in New York City…

Where to stay?

It's highly recommended to find accommodation within Manhattan itself. The island is packed with places to stay, none of which are cheap. You can also stay in Brooklyn or Queens near a subway station.

Click here for all the information you need about finding a place to stay in New York hotels…

Click here for a list of 12 great hotels in Manhattan…

Expert Tips for Travelers in New York

• Even though it's essential to keep a neat appearance, it's highly recommended to come on a trip with comfortable clothes (suitable for the season) and especially with comfortable shoes!!!
• The heart of the city and the base for a tour in Midtown is Times Square, from which all of Midtown's sites and attractions are a short walk away
• The main axis of the Midtown tour is Fifth Avenue, considered the unofficial boundary line between Midtown East, Times Square area to the north, and the Garment District to the south
• Since getting around the city is really easy and convenient with the subway (and also with buses), you can shorten walking times by using the subway for one or two stops.
• From Midtown, you can easily get to Uptown, to the Museum Mile on the Upper East Side, along Central Park and the beautiful streets of the Upper West Side. You can also mix in a day trip to neighborhoods south or west of Midtown like Hell’s Kitchen, Chelsea, Greenwich Village, SoHo, and the Lower East Side.
• Midtown is the main entertainment area in Manhattan during the evening and night hours. Besides visiting Times Square during the travel itinerary, it’s definitely worth seeing the dazzling square also at night.

Map of Midtown Manhattan Travel Routes

Detailed Itinerary of Midtown Manhattan Days

Day Trip 1: Manhattan – The Major Squares of Midtown – From Times Square to Union Square

On the first day, we're diving into the vibrant energy of Midtown Manhattan. Today's walk will highlight the famous squares along Broadway – from Times Square, through Herald Square, Madison Square, to Union Square. We'll take a route that connects these squares, hitting all the nearby sites and attractions along the main strip. This is truly the heart of Midtown, featuring the city's iconic skyscrapers like the Empire State Building and the Flatiron, and the streets of the Theater District, Garment District, Koreatown, and Flatiron District.

Times Square Area

1. We'll kick off our tour of Manhattan at the most central junction in the USA, at the intersection of Seventh Avenue with Broadway – Times Square. The square is the heart of the theater district and an amazing place for shopping. We'll skip all the fun for now and start our tour (of course it's worth coming back to the square separately for shopping, eating, or strolling around in the evening).
2. Around the square, there are quite a few important towers and buildings including MTV Studios (where they broadcast live and film the plaza beneath), the legendary Sardi's restaurant, Westin Hotel, Fairmont Hotel, Paramount Building, and several large theaters like the Lyceum and Minskoff. Another icon in the square is the news ticker on the facade of the Morgan Stanley building, displaying the data of the New York Stock Exchange.
3. From the square, let's walk half a block on West 45th Street to Shubert Alley, the ground zero of Broadway and the New York theater world. In the alley, you'll find the Booth Theatre and Shubert Theatre. Nearby streets host many other active theaters like the Broadhurst, St. James, The Hayes, Gerald Schoenfeld Theatre, Bernard B. Jacobs Theatre, the Majestic, and more.
4. From the square, we walk east on West 42nd Street and arrive at Bryant Park. This park is mostly a beautiful green space, and sometimes hosts various fairs, fashion shows, or even filming for TV series and movies.
5. On the eastern side of Bryant Park stands the impressive structure of the New York Public Library. At the front of the library on Fifth Avenue there are classical columns and Greek-style sculptures in Renaissance niches with Corinthian capitals, among which are the famous lion statues. The main reading room is a vast space, a masterpiece of architecture, combining an abundance of light that streams in from outside and illuminates the library's millions of books and manuscripts.

South Midtown

1. From the library, we'll head south on Fifth Avenue, walking seven blocks under the shadows of skyscrapers until we reach a masterpiece from New York's golden era. We'll enter the Empire State Building and ascend to its famous observation deck, 1,250 feet above the bay waters. On the way, we'll stop at the first observation deck on the 86th floor, then take another set of speedy elevators to the 102nd floor.
2. We'll leave the magnificent skyscraper, head one block south, and stroll west on 32nd Street through what's known as Koreatown until we reach Herald Square – where Broadway meets Sixth Avenue.
3. At the northern end of the square, we’ll enter the giant department store Macy's, the largest store in the USA.
4. We'll cross the store lengthwise and exit onto Seventh Avenue directly to the circular plaza of the Madison Square Garden. This is the home arena of Manhattan's two famous teams: the New York Knicks (basketball) and the New York Rangers (hockey). Beneath the stadium is the structure of Pennsylvania Station or Penn Station.
5. On the southern side of the stadium, we'll see the beautiful facade of the 19th-century Catholic Church of St. John the Baptist. We'll be impressed by the stunning interior of the church and return to Herald Square.

Flatiron, Gramercy Park, and Union Square

1. From Herald Square, we'll head south on Broadway to Madison Square Park, the intersection of the diagonal street with Fifth Avenue. The square features beautiful statues, a fountain, and monuments.
2. On the southern part of the square towers one of Manhattan's most unique and iconic skyscrapers – the Flatiron Building. The building is shaped like an acute triangle, with its narrow façade facing Madison Square Park, mirroring the path of Broadway. The structure was completed in 1902 and is considered one of New York's architectural gems.
3. From Madison Square, let's head east into the beautiful streets around Gramercy Park. The park's gardens are closed (only open to residents around the park), but we will walk around it and admire the beautiful mansion houses and the National Arts Club.
4. From the park, we'll head slightly west and walk south down Park Avenue South to Union Square. The square is identified with natural and organic culinary stores, including a famous organic food market held here. Around the square are many shops and bookstores, and a huge Whole Foods Market on its southern side.

Day Trip 2: Manhattan – Upper Midtown and Midtown East

Our second day of touring will focus on the unimaginable wealth of the area between Times Square and Central Park and the famous avenues of the East Midtown – Fifth Avenue, Madison Avenue, Park Avenue, and Lexington. This is the heart of New York's shopping world (on the more luxurious side) against the backdrop of some of the most iconic skyscrapers in the world, along with important museums such as MoMA and the Rockefeller Center complex.

Upper Midtown

1. We'll start our tour in Upper Midtown at Columbus Circle, where Broadway meets Eighth Avenue, and the southwestern edge of Central Park.
2. At the Circle, we'll enter the Museum of Arts and Design which boasts a giant collection of over 2000 design pieces that were considered groundbreaking in their time.
3. From the museum, walk along West 59th Street on the edge of the park and go one block south to Alwyn Court, considered one of the most ornate and distinctive residential buildings in the city.
4. Continue one block south on Seventh Avenue and arrive at Carnegie Hall, the largest and probably the most famous concert hall in New York.
5. From Carnegie Hall, head one block south to the New York City Center – the urban center for music and dance known for its unique Moorish-Spanish architecture.
6. Head back north on Sixth Avenue to the edge of Central Park and walk to the southeast corner of the park where you'll find The Plaza Hotel, arguably the most iconic hotel in New York.
7. Continue to Grand Army Plaza, where the famous Apple Store is located.

Fifth Avenue

1. From Grand Army Plaza, continue east on 59th Street until you reach Lexington Avenue, where you will find the famous department store Bloomingdale's. The flags above the store's entrance have appeared in numerous film series (countless times in “Friends”) and there’s hardly an American series set in New York where the characters haven’t visited the department store at least once.
2. From Bloomingdale's, head south on Lexington Avenue until you reach the Central Synagogue of New York, one of the largest and most famous synagogues in the world.
3. From the synagogue, walk two blocks north to East 57th Street and head west towards Fifth Avenue to Trump Towers. These towers are the pinnacle of the 80s skyscraper genre, full of grandeur and black granite bricks. Take a stroll through the building's kitschy interior and also visit the famous Tiffany & Co shop (from Truman Capote's “Breakfast at Tiffany's” and the song, of course).
4. Next to the Trump building, we'll see the IBM computer company's tower. At the building entrance is the Levitated Mass sculpture by artist Michael Heizer. Across the avenue, another impressive skyscraper stands out, 432 Park Avenue, the fifth tallest building in New York, dedicated entirely to luxury residences.

The Diamond District

1. We'll head south down the most luxurious and glamorous part of Fifth Avenue and turn on 53rd Street West until we reach the entrance to the Museum of Modern Art (MoMA). MoMA houses an extraordinary number of important paintings from all modern art movements – from Impressionism to the popular culture of the USA in the fifties.
2. From MoMA, we'll head south on Sixth Avenue to the Radio City Music Hall, the massive performance venue at the northern edge of the Rockefeller Center complex.
3. Rockefeller Center consists of about 19 commercial and business towers in two complexes. The center is located across two entire blocks between Fifth and Sixth Avenues, and between 51st and 49th Streets. We'll start our tour at the center with a climb to the Top of the Rock observation deck for a view of midtown's skyscrapers.
4. From the observation deck, we'll head to the ice skating rink, above which stands the famous Prometheus statue, the symbol of the center. We'll exit the center towards Fifth Avenue, where we will see the Atlas statue holding the world on his shoulders.

Midtown East

1. From Rockefeller Center, we'll embark on a tour down Fifth Avenue, the pinnacle of New York shopping and one of the most stunning urban spectacles globally.
2. We'll cross the avenue from Rockefeller Center and the Atlas statue to enter the luxurious department store Saks Fifth Avenue. For those who want to admire or shop, you can wander around the giant department store for a bit.
3. We'll leave the department store and head north to our neighbor – St. Patrick's Cathedral, the most important church building in New York.
4. From the cathedral, we'll head east on 50th Street East to the impressive building of Waldorf Astoria Hotel. The original location of this luxury chain hotel was where the Empire State Building stands today. The current building was constructed in 1931 in a stunning Art Deco style.
5. Adjacent to the hotel to the north, we'll see the General Electric Building. This skyscraper was built in the 1930s as a tall and narrow tower crowned with a dome inspired by Gothic cathedrals. The Gothic crown blends with St. Bartholomew's Church which is next to it on the west.
6. From the hotel and General Electric, head south on Park Avenue and take in the stunning view of the MetLife Building, a masterpiece of the International Style. Beneath the skyscraper, step into the spectacular space of Grand Central Terminal, home to the famous clock facing all four directions. Exit from the front of the station, where you'll find classical-style sculptures with themes of Greek gods.
7. From the station, walk one block east on 42nd Street to reach the Chrysler Building, one of the most beautiful and famous skyscrapers in Manhattan. At the top of the tower is an Art Deco spire made of overlapping semicircles arranged in a pyramid shape, reminiscent of the radiator caps on Chrysler car models.
8. Continue from the Chrysler Building along 42nd Street to the United Nations Building, which includes the General Assembly Hall and the conference room used by the Security Council. Completed in 1951, the building stands on the banks of the East River.
9. From the UN Building, we'll head back north through the elegant Dag Hammarskjold Plaza to Lexington Avenue.