The Insider’s Guide to Three Perfect Days in New York City

For something buzzy, the revitalized Waldorf Astoria is an absolute visual treat, from its signature lobby lounge to the iconic clock. This is no ordinary hotel; it’s a piece of Manhattan history, and you’ll want to soak that in, whether you’re sipping a martini at its two-story brasserie or checking into a Pierre-Yves Rochon-designed suite overlooking Park Avenue. For another side of the city’s history, head straight to the Hotel Chelsea. The version of Patti Smith and Leonard Cohen’s era may be long gone, but its story is still fiercely celebrated, whether through longtime residents who remain in its apartments or the vintage fireplaces and stained glass of its interiors. Still, contemporary perks are woven into this living museum, including a fabulous spa.

From the minute you enter Nine Orchard, you feel like a more stylish version of yourself. Credit the venerable address (it’s housed in the historic 1912 Jarmulowsky Bank Building), the chic design (the lobby combines midcentury furniture with maximalist Gucci wallpaper), and the expansive city views. Plus, it boasts one of my favorite bars in town, the lush Swan Room. Moody and sleek, the Ritz-Carlton, Nomad is also designed to make an impression—and not just because of its 50-story sway. Inside, dramatic interiors set the tone, matched by excellent service. Must-try food and drink experiences include Spanish-Japanese fusion at The Bazaar by José Andrés and rooftop cocktails at Nubeluz, a jewel-toned bar with views for miles. Equally impressive, the exuberantly designed Fifth Avenue Hotel is a wondrous escape from the busyness of NoMad that lives just beyond its doorstep. Stockholm-born designer Martin Brudnizki has filled it with a romantic enthusiasm that is both transportive and cocooning. Leave room for a nightcap at the snug, wood-paneled Portrait Bar—or order up a martini cart to your suite.

1 Hotel Brooklyn Bridge is a good option if you’re looking for views over Brooklyn Bridge Park and coveted panoramas of Downtown Manhattan—it draws a loyal following of younger, sustainability-minded travelers who appreciate its green ethos. At any given moment, the plant-filled lobby is dotted with stylish locals and tourists alike, and the rooftop buzzes all summer long.

Day 1: Upper East Side

Breakfast spot: Babka (and more) at Breads Bakery

Morning activity: Jog the reservoir

Jacqueline Kennedy Onassis Reservoir

Do as locals do and go for a run along the 1.58-mile loop around the Jackie O Reservoir—but pause at one of its many scenic overlooks for city views or glimpses of its resident herons and coots.

Lunch spot: Comfort food at Café Sabarsky

Afternoon activity: Get lost at The Frick

You’re bound to make time for institutions like MoMA and the Guggenheim, but allow me to point you toward the newly reopened Frick Collection. Housed in a Gilded Age mansion on Fifth Avenue and 70th Street, it’s especially strong in Old Masters and European sculpture—and can be toured in just over an hour.

Dinner: French fare at Chez FiFi

Chez FiFi, an elegant mahogany-paneled French restaurant tucked into a townhouse on 74th Street, is ideal for special occasions—and expense account-style splurges. With only 40 seats in the main dining room, you’ll have to snag a table early.