Midtown Manhattan Shopping Tour (Self Guided), New York

Long before Manhattan’s tidy street plan straightened everything out, Broadway, unlike other streets in New York, followed an older native pathway, wandering freely up the island. This is why it slices across Seventh Avenue and 42nd Street, forming two triangular pockets, like a bow tie. The southern one is called Times Square, while the northern, Duffy Square, is named for World War I chaplain Father Francis P. Duffy, whose statue now watches over the crowds with admirable patience.

The stretch of Broadway from 41st to 53rd Streets goes by a different name: the Great White Way. That nickname wasn’t poetic exaggeration—those glowing billboards, marquees, and oversized posters once made the area one of the brightest electrified spots on Earth. Today, it’s still blazing away with advertisements for Broadway’s latest musicals and plays, pulling in nearly 50 million visitors a year. That’s roughly 330,000 people a day, all weaving through the lights, noise, and spectacle in search of something unforgettable.

Before it was Times Square, this chaotic crossroads answered to the far calmer name of Longacre Square. Everything changed in 1904, when New York Times publisher Adolph S. Ochs moved his newspaper into the brand-new Times Building—now known as One Times Square—and happily lent his name to the neighborhood. The Times moved out within a decade, but not before launching a little tradition in 1907: the New Year’s Eve Ball Drop. A century later, the glittering descent still draws over a million people every year, along with countless viewers around the world.

Today, Times Square is a fluorescent buffet of attractions—ABC’s Times Square Studios, Planet Hollywood, Bubba Gump Shrimp Company, and whichever character impersonator is bravest that day. The towering illuminated signs, nicknamed “spectaculars” or “jumbotrons,” compete with the neon bravado of Las Vegas and often win.

Amid all that glow, shoppers duck into stores like Gap, Old Navy, Forever 21, Levi’s, the Disney Store, Hershey’s Chocolate World, and M&M’s World—each one flashing its own brand of temptation. Whether you’re hunting for a souvenir, a show, or just a moment to stand still and stare, this Midtown crossroads remains New York at its most unfiltered and unmistakable.

Back in 1801, a New York physician named David Hosack bought 22 acres of empty land from the city with an aim to establish America’s first botanical garden. And for the next ten years, the Elgin Botanic Garden really did bloom—until funding wilted, the plants went wild, and Columbia University had to step in to take over the property in 1823.

Fast-forward a century to 1926, when the Metropolitan Opera went searching for a grand new home. Columbia leased the land to its generous patron, John D. Rockefeller, Jr., setting the stage for a glittering cultural palace. Then the stock market crashed in 1929, the opera backed out, and Rockefeller found himself with prime New York real estate and no tenant. So, he pivoted—and decided to build a mass-media powerhouse instead.

In 1930, after months of negotiations involving Radio Corporation of America, National Broadcasting Company, and Radio-Keith-Orpheum, the plan was set: an entertainment complex of unprecedented scale. To make room, 228 buildings were cleared and 4,000 tenants relocated. Early name ideas included “Radio City,” “Rockefeller City,” and the dramatic “Metropolitan Square,” before the now-famous title finally stuck.

Today, Rockefeller Center stretches across all of Doctor Hosack’s original 22 acres—though the botanicals have long been replaced with 14 Art Deco buildings, a standalone tower along 51st Street, and four more rising on the west side of Sixth Avenue. There are rooftop gardens, but you’ll have to crane your neck to see anything green.

On the west side sits Radio City Music Hall, still flashing its neon glamour. And at the heart of it all lies the sunken Lower Plaza, praised by Chinese-American architect Ieoh Ming Pei as “the most successful open space in the United States, perhaps in the world.” Most visitors simply know it as “the place with the ice rink,” which has been delighting skaters since 1936.

Then there’s the view. “Top of the Rock” offers three levels of indoor and outdoor decks with clear, cinematic vistas of the New York skyline. Back on the ground, the shops spread out in every direction—big names, small designers, and everything in between. It’s the kind of place where you realize: shopping isn’t just about what you buy; it’s about where you buy it...

5th Avenue is a major thoroughfare in New York City's Manhattan, extending north from Washington Square Park in Greenwich Village to West 143rd Street in Harlem. It is considered one of the most expensive and luxurious stretches of retail in the U.S., if not the whole world, which has been drawing a steady stream of fashion addicts for over a century now.

Few things can be equally fun and indulgent as shopping (or even window-shopping) at 5th Avenue, as most of the high-end designer outposts here feature ornamental window displays and, on any given day, the street resembles a couture runway. However, the experience can also be just as daunting and overwhelming, particularly for first-time shoppers, so here are some of the top shops worth checking out primarily on 5th Avenue:

- Tiffany & Co. is the incredibly famous fine jewelry brand flagship store where the iconic “Breakfast at Tiffany's” movie was set.
- Known worldwide, despite this being their only location, Bergdorf Goodman is the premier shopping destination for all luxury items. Many celebrities have been quoted as saying "Scatter my ashes at Bergdorf's".
- If you look for high-quality cultured pearls as a memorable gift for a special lady in your life, then look no further than Mikimoto.
- If you're lusting after the new iPhone or are just a tech lover, a visit to The Apple Store is a must.
- The crème de la crème of leather handbags, the outpost of French Louis Vuitton will set you back a hefty sum for a purse, but, given the timeless style, you'll be able to wear it for years to come.
- The Italian brand Prada offers a wide variety of luxury items, from fashion to shoes and handbags, and everything in between.
- Well-made suits for the well-heeled set are found in abundance at Hugo Boss, notorious since the late 1990s, courtesy of “The Sopranos” series.

Why You Should Visit:
The main artery of New York City's shopping scene with mass brands, upscale department stores and multinational retailers offering something for everyone.

Running south-north from Madison Square (at 23rd Street) to Harlem River Drive (at 142nd Street), Madison Avenue passes through Midtown and further up the Upper East Side, East Harlem, and Harlem. The avenue is named after the place it arises from, Madison Square, which in turn has been named after James Madison, the fourth President of the United States.

The street's name has been metonymous with the American advertising industry since the 1920s. Thus, the term "Madison Avenue" refers specifically to the agencies and methodology of advertising ("Madison Avenue techniques" – the gimmicky, slick use of the communications media to play on emotions).

Interestingly enough, more recently, in 1984, the "Splash" movie gave rise to a new naming trend in the U.S. associated with Madison. In this film, a mermaid, who has adopted a human form, takes the name Madison after she sees it on a street sign. Ever since then, Madison, which had previously been an exclusively male name (meaning "son of Maud", Maud's son), has been used by females and become one of the most popular names for girls in the United States.

Similarly to London's Oxford Street and the neighboring Fifth Avenue, Madison Avenue is known for its fashionable shops, especially in the section between 57th and 85th Streets, exhibiting timeless elegance with a contemporary flavor that is distinctively New York. This premier luxury district is a home to flagship boutiques of the finest fashion (& jewelry) designers like Tom Ford, Giorgio Armani, Calvin Klein, Luca Luca, Hermes, and Carolina Herrera. Numerous world class art galleries and the Whitney Museum of American Art are also found here alongside internationally renowned hotels such as the Mark, the Pierre, and the Carlyle. The exquisite local restaurants, spas and salons are geared to deliver exclusive pampering to the rich and famous.

Bloomingdale’s at 59th Street and Lexington Avenue is the flagship store of Bloomingdale's Inc., a luxury retail chain, founded in New York City by Joseph B. and Lyman G. Bloomingdale in 1861. More than 150 years later, the brand has become a household name denoting a network of 36 department stores operational across the United States.

But there’s still nothing like a shopping spree in Bloomingdale’s huge original location, with its characteristic black-and-white checkered marble floor and all-around luxe atmosphere. Ranking among the city’s top tourist attractions, Bloomie’s in Manhattan is extremely popular for the huge selection of quality items it carries. Over the years, their signature brown shopping bags (with a “big-”, “medium-” or “little brown bag” written on them) have become a girl’s best friend – you can see hundreds of them carried around the city, as you walk.

While the Bloomingdale’s selection is, indeed, the most extensive for younger or trendier women, featuring everything from shoes and handbags to designer duds and housewares, within its eight floors there’s plenty of merchandise for men, too. If not for themselves, you can often see them roaming the store to secure a perfect gift for their significant other. With this in mind, the Bloomingdale’s cosmetics hall is definitely not be missed whenever there is someone you know who deserves something special.

You can easy spend the entire day in this 815,000 square-foot venue, browsing high-end décor and merchandise from hundreds of brands, as well as indulging in their on-site dining options.

Running one-way southbound for its entire length, from 131st to 21st Streets, Lexington Avenue is largely commercial at the ground level, with offices above. Alongside the clusters of hotels in the 30s and 40s, there are numerous structures on Lexington designated as New York City Landmarks, National Historic Landmarks, and National Register of Historic Places.

Still, when it comes to attractions, the avenue is known primarily for its unique and more affordable shopping that makes Lexington stand out from the more touristy neighbors like Madison, Park, and Fifth Avenues. Most of Lexington's shops are relatively little-known outlets offering rather specific products. Transitioning from Midtown to the Upper East Side, the 20-block stretch from 50th to 69th street houses a variety of small stores, including jewelry, shoe, and home furnishing boutiques.

Among the ones worth visiting here are Elle W Collection, a high-end antique jewelry and home furnishings dealer (864 Lexington Avenue); Pan American Pheonix, specialized in hand-made Mexican clothing, accessories, and pottery; Diane B. Lady Shoes (at 63rd street) for women's shoes and handbags; and Galo (at 63rd street) for men's and women's comfortable and reasonably priced footwear, including comfortable shoes for wedding. And if you're shopping for a gift, stop by Le Sabon and Baby Too (at 64th street), which carries dainty gift items and adorable baby shower gifts.

Lexington Avenue is also home to a number of well-known retailers, such as Bloomingdale's, Zara, Levi's, and Nine West, offering a wide range of clothing, from moderately priced to some rather expensive, trendy garments.