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Where to begin when describing the iconic Four Seasons? Why not start with some name-dropping: Marilyn Monroe, Martha Stewart, Barbara Walters and Henry Kissinger have all been loyal guests, while countless other celebs dine and drink here regularly. (Note: The hotel's restaurant is the 57 and L'Atelier, not the power-lunching hot spot known also as the Four Seasons; there's no relationship.). The 52-story limestone structure was designed by I.M. Pei, mastermind behind the controversial glass pyramids at the Louvre. Pei's stunning 33-foot-high, backlit onyx ceiling at the Four Seasons prompted Jackie O to refer to her favorite haunt as "The Cathedral." The city's tallest hotel and frequent winner of magazine "Best Of" awards, the Four Seasons' rooms and suites average about 600 square feet—about the size of a typical Manhattan one-bedroom apartment. Ten-foot high ceilings, large marble bathrooms, deep-soaking tubs and furnished terraces add to the allure, while swishy, controlled-from-the-bed silk drapes peel back to reveal stunning views of Manhattan—no matter what the season. For business guests, rooms have faxes and high-speed Internet access and the basement has a center computer with workstations, secretarial and interpreting services, and cell phone and laptop rental. Off to a meeting or a lunch date? The hotel can arrange a car and driver. The service here is amazing. — Nick Divito

Those who can afford it shouldn't need convincing, but details like the famous Four Seasons beds, twice-daily maid service, an excellent on-site spa and impeccable service might help seal the deal.

Cons
Although it's a veritable Big Apple icon, its rooms don't reflect anything specific about the city. Close the drapes and you could be at any Four Seasons in the country.

Claim to Fame
This was where JFK held his birthday bash before Marilyn Monroe crooned "Happy Birthday" at Madison Square Garden. Also, the hotel's bar claims to have invented the Bloody Mary.

Weddings
For old-world glamour, this serene, luxurious hotel is tops—which is why it generally books about a year in advance. Guests can mingle on the gorgeous lobby terrace before they are led to any number of great rooms. The biggest, called the Cosmopolitan Suite, holds 165 guests for cocktails and has a clubby, cabaret feel; several smaller rooms can accommodate groups of 50. Catering starts at $275 per person.

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