Madison Avenue, New York City

Armani, Madison Avenue.

Madison Avenue is home to the bulk of Manhattan’s snobbiest retail establishments, which are packed into a twenty-block stretch between East 58th and East 78th streets. Retail rents here are the highest in the Big Apple, and some of the highest in the world.

This posh section of Madison Avenue is located on the Upper East Side, two blocks east of Central Park, and I think you’ll agree that the pedestrian experience is better here than on Fifth. Buildings are shorter, allowing more light to reach the street, traffic is lighter, and there’s somewhat more greenery.

Ritzy retail: Alexander McQueen, Baccarat, Balenciaga, BCBG Max Azria, Bottega Veneta, Calvin Klein, Canali, Carolina Herrera, Cartier, Céline, Chanel, Chloé, Chopard, Christian Louboutin, David Yurman, Dior, Dolce & Gabbana, Elie Saab, Fendi, Frette, Giorgio Armani, Gucci, Hermès, Jil Sander, John Varvatos, Ladurée, Lalique, Lanvin, Max Mara, Michael Kors, Montblanc, Oscar de la Renta, Pucci, Ralph Lauren, Sonia Rykiel, Stella McCartney, Tod’s, Tory Burch, Vacheron Constantin, Vera Wang.

Michelin-starred area restaurants: Daniel; Caviar Russe.

AAA five-diamond area hotels: the Pierre; Four Seasons New York.

Experience: we’ll pause to examine the elaborate French Renaissance Revival architecture of the Gertrude Rhinelander Waldo Mansion (at East 72nd Street), which dates to 1898. It now houses the Ralph Lauren men’s flagship store.