Gramercy

Perhaps best known for the famous locked park for which only residents and hotel guests have keys, Gramercy also more or less extends to Union Square Park, the famous Flatiron Building, and the birthplace of Theodore Roosevelt. There is a certain amount of overlap with the Flatiron District, of course, which is par for the course in New York City. The Flatiron/23rd Street Partnership also sponsors free 90-minute walking tours of the historic district, in which you're sure to see some of the city's most notable landmarks, including the New York Life Insurance building, the MetLife tower, the Appellate Courthouse and of course the Flatiron Building. Explore the world’s first skyscraper, the triangle-shaped, eighteen-story Flatiron Building that dates back to 1902. It is only six feet wide at the apex of the triangle! Or visit the Greenmarket at Union Square, a park first landscaped in 1832, where the Department of Parks kept its offices until the 1870s.

Head on to the Theodore Roosevelt Birthplace National Historic Site at 28 East 20th Street, between Broadway and Park Avenue South. The house was reconstructed in 1923 and has interesting period rooms and a small museum dedicated to the nation's 25th president. The National Arts Club, which hosts a number of exciting events including art unveilings, award dinners, film screenings, lectures and dances is also in the neighborhood.

In terms of dining and nightlife, there are also plenty of options. For unique, inventive American cuisine try Gramercy Tavern. Do try the roasted sweetbreads, the chilled lobster and the seared foie gras appetizers—the latter two do have a supplemental charge that is well worth the price. There's also the Strip House, which serves some of the finest steaks in New York. And if you find yourself getting thirsty stop for a drink at the legendary Pete's Tavern the place that writer O. Henry made famous. Open since 1864, its New York's oldest surviving saloon. It even operated during Prohibition disguised as a flower shop. Later on, if you're looking to liven up your night catch a concert at Irving Plaza, a midsize venue that lots of big indie rock bands play.

In addition to the renowned Gramercy Park Hotel, the neighborhood is also surrounded by various other illustrious hotels. There's the über-swanky Hotel Giraffe as well as the luxurious W New York Union Square. Designed in the Beaux-Arts style it is a magnificent granite and limestone structure with all the exquisite details inherent in traditional European architecture. For the more budget conscious traveler there's always the Chelsea Inn and Hotel 17.

Right nearby is the self-proclaimed, original Silicon Alley that gets its name from the numerous internet related companies in the area. The alley snakes down Broadway, although by now nearly any part of Manhattan below Gramercy Park qualifies as Silicon Alley. Finally, take a peek at Gramercy Park itself, its well-manicured green space and beautiful flower beds. Maybe someone will invite you in; ask nicely—you never know!