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When Colonel John Jacob Astor envisioned this grand hotel in 1902, he dreamed of combining European elegance with American advancements. The St. Regis was housed in a eighteen story Beaux Arts building, the tallest structure on this stretch of Fifth Avenue, and was one of the first to have an elevator and boast such modern innovations as a cooling system (a forerunner of today’s air conditioning). All the materials and furnishings, however, were imported from Europe, an extravagant and much talked-about expense (the hotel ended up costing $5.5 million, an unheard of sum at the time). The original inventory list included three Steinway pianos, china by Royal Worcester and Royal Minton, a set of solid gold flatware and handmade bed linen from Germany.

Today, arriving at the St. Regis, you’re still surrounded by turn-of-the-century elegance. There’s the gilded lobby with its pastel-colored ceiling fresco; the small Cigar Lounge with an immense marble fireplace, twisted Art Nouveau chandelier and dark-wood paneled walls; there are the original marble floors. But the friendly staff, a recent refurbishment and the lively King Cole Bar, presided over by Maxfield Parrish’s famous mural, keep the St. Regis from feeling stuffy or dated. The 164 rooms are done in a pretty palette of slate blue and gray; the 65 suites are cheerful cream and gold. The smallest room measures 430 square feet and lovely decor touches—all the rooms, save for some specialty suites, received a recent update from interior design firm Sills Huniford—include silk wall coverings, restored ceiling moldings and plush queen- and king-size beds. Bathrooms are spacious, clad in marble and stocked with Remède products. The St. Regis has several specialty suites, including the most recently added Bottega Veneta Suite, a two-bedroom extravaganza that was designed by the Italian leather company’s artistic director Tomas Maier.

Each floor comes with a butler, who can assist with anything from arranging a spa appointment to rushing forgotten luggage to the airport. During a stay, guests receive two complimentary pieces of clothing pressed and a shoe shine, thoughtful details that fulfill Astor’s original vision of making his hotel feel more like a private residence (Salvador Dalí lived there for thirteen years). Past visitors also rave about how the St. Regis staff goes out of its way to make families traveling with children feel at home, beginning with check in where guests receive an upgrade if one is available.

In 2005, the St. Regis added the small Remède Spa, with four treatment rooms, which is open until 9p.m. every night (non guests can make appointments here as well). The layout is somewhat jarring, as spa and gym share the same area, but the treatments are top-notch and the experience decadent from the moment you arrive—instead of water or tea, you’re offered Champagne and Jacques Torres chocolates.

In January 2008, French star chef Alain Ducasse opened his much-anticipated second New York restaurant, Adour It places a bigtime emphasis on wine with bottles displayed in private wine vaults and temperature-controlled armoires. David Rockwell designed the space which features such high-tech gadgetry as wine tasting notes projected onto the top of the interactive wine bar. An acclaimed French chef and an American designer collaborating on one of the toughest tables to book? It sounds like a combination that would make John Jacob Astor proud. Rooms from $995.

TIP: With standard rooms starting at $995, it’s worth splurging on the $1,300 suites, which come with a spacious living room, a calm spot for inviting friends for a drink or coffee if the King Cole Bar is too crowded. SIMONE GIRNER

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With the Plaza and the Stanhope being converted into apartment buildings (as the Westbury and Mayfair already have been) and the Waldorf taken over by conventions, there is only one historic grand hotel left in the city: the Carlyle, on East 76th Street and Madison Avenue. (The southeast corner of this intersection has been officially named Bobby Short Way in honor of the legendary piano man and song stylist who performed regularly in the hotel bar right up to his death in 2005.) Since the hotel opened, in 1930, it has been a bastion of discreet luxury and the address of choice for movie stars—Sienna Miller and Jude Law stayed here last June—and high-net-worth men in the midst of a dalliance or of a divorce. (President Kennedy and Marilyn are said to have trysted at the Carlyle.)

The lobby and the Bemelmans Bar have been given fresh polish by interior designer Thierry Despont, who managed to keep it glamorous but restrained (click here to read about a fun new afternoon tea option for kids). Today the gleaming black and white marble and the velvet couches form a backdrop as elegant as the one Ingrid Bergman found when she first stayed at the hotel in the late ’30s. Over the years, different decorators, including Dorothy Draper and Mark Hampton, have brought their visions of gracious New York living to bear on the 181 guest rooms. Some, however, are heavy on chintz and Audubon prints, making them feel dated and faded and in need of the full treatment that the dining room and Royal Suite received last year from the hugely talented designer Alexandra Champalimaud. Tip: Ask for one of the renovated guest rooms with a view. Rooms from $700.

TIP: Read about a special package the hotel is offering in conjunction with Olafur Eliasson’s Waterfall Project.