Iconic New York: City & Beyond
A whirlwind 5-day dive into the concrete jungle, classic skyline views, and a scenic escape to the Hudson Valley.
JFK → Midtown → Central Park → Lower Manhattan → Brooklyn → Sleepy Hollow → JFK
Midtown Classics & Skyline Heights
Grab your bags and pick up the rental. It’s about an hour's crawl into Manhattan, so settle in and enjoy the first glimpse of the skyline from the Van Wyck Expressway.
John F. Kennedy International Airport (JFK)
Grab your bags and pick up the rental. It’s about an hour's crawl into Manhattan, so settle in and enjoy the first glimpse of the skyline from the Van Wyck Expressway.
Grand Central Terminal
Grand Central Terminal is a commuter rail terminal at 42nd Street and Park Avenue in Midtown Manhattan, New York City. Grand Central is the southern terminus of the Metro-North Railroad's Harlem, Hudson and New Haven Lines, serving the northern parts of the New York metropolitan area. It also serves the Long Island Rail Road through Grand Central Madison, a 16-acre (6.
New York Public Library - Stephen A. Schwarzman Building
Walk past the stone lions, Patience and Fortitude, to see the Rose Main Reading Room. It’s quiet, majestic, and free.
Summit One Vanderbilt
One Vanderbilt is a 62-story supertall skyscraper at the corner of 42nd Street and Vanderbilt Avenue in the Midtown Manhattan neighborhood of New York City. Designed by Kohn Pedersen Fox for developer SL Green Realty, the skyscraper opened in 2020.
Times Square
Broadway. Times Square. Madison Square Garden. The name says it all: the Theater District is the entertainment hub of the city, and possibly the entire nation. The western half of Midtown Manhattan (to be distinguished from Midtown East), this is where you'll find Times Square, the streets packed with people taking in one of the brightest entertainment districts in the world.
Museum Mile & Green Escapes
Day 2｜Museum Mile & Green Escapes (10km, 0.4h drive)
The Metropolitan Museum of Art
The Metropolitan Museum of Art, colloquially referred to as the Met, is an encyclopedic art museum in New York City. By floor area, it is the fourth-largest museum in the world and the largest art museum in the Americas. With 5,727,258 visitors in fiscal year 2025, it was the most-visited museum in the United States and the fourth-most visited art museum in the world.
Central Park
A vast green swath of open space in the heart of Manhattan, Central Park is a district in its own right, neatly separating the Upper East Side from the Upper West Side, stretching from Midtown at the southern end to Harlem at the north.
American Museum of Natural History
The American Museum of Natural History (AMNH) is a natural history museum on the Upper West Side of Manhattan in New York City. Located in Theodore Roosevelt Park, across the street from Central Park, the museum complex comprises 21 interconnected buildings housing 45 permanent exhibition halls, in addition to a planetarium and a library.
Lincoln Center
Lincoln Center for the Performing Arts is a 16.3-acre (6.6-hectare) complex of buildings in the Lincoln Square neighborhood on the Upper West Side of Manhattan. It has thirty indoor and outdoor facilities and is host to five million visitors annually.
Downtown Grit & Statue Views
Walk this elevated park built on a historic rail line. Start at 30th St and walk south toward Chelsea Market for a coffee and taco breakfast.
The High Line
The High Line is a 1.45-mile-long (2.33 km) elevated linear park, greenway, and rail trail created on a former New York Central Railroad spur on the West Side of Manhattan in New York City. The High Line's design is a collaboration between James Corner Field Operations, Diller Scofidio + Renfro, and Piet Oudolf.
Greenwich Village
Greenwich Village (often referred to as "West Village" or simply "the Village") is a well-known, largely residential district in Manhattan, once famous for its vibrant art and literary community.
9/11 Memorial & Museum
A heavy but necessary stop at Ground Zero. The reflecting pools are incredibly moving.
The Battery
Walk to the tip of Manhattan. You can catch the free Staten Island Ferry for a great view of the Statue of Liberty without paying for a tour.
Wall Street
The Financial District comprises the southern tip of Manhattan, with the Hudson River on the west, the East River on the east, New York Harbor to the south, and Barclay Street on the north.
Brooklyn Vibes & Bridge Walks
DUMBO
Dumbo is a neighborhood in the New York City borough of Brooklyn. It encompasses two sections: one situated between the Manhattan and Brooklyn Bridges, which connect Brooklyn to Manhattan across the East River, and another extending eastward from the Manhattan Bridge to the Vinegar Hill area.
Brooklyn Bridge Park
Brooklyn Bridge Park is an 85-acre (34 ha) park on the Brooklyn side of the East River in New York City. Designed by landscape architecture firm Michael Van Valkenburgh Associates, the park is located on a 1.3-mile (2.1 km) plot of land from Atlantic Avenue in the south, under the Brooklyn Heights Promenade and past the Brooklyn Bridge, to Jay Street north of the Manhattan Bridge.
Brooklyn Bridge
Downtown Brooklyn is in Brooklyn. In addition to the downtown area proper, it includes Brooklyn Heights, DUMBO, Cobble Hill, Boerum Hill, Fort Greene, Clinton Hill, and the Navy Yard.
Williamsburg
Williamsburg is a city in southeast Virginia. Settled in 1632, it was the capital of Virginia from 1699 to 1779 and in 1926, John D. Rockefeller Jr commissioned a restoration project to bring Williamsburg back to its former colonial glory.
Bushwick
Bushwick is a neighborhood in the northern part of the New York City borough of Brooklyn. It is bound by the neighborhood of Ridgewood, Queens, to the northeast; Williamsburg to the northwest; the cemeteries of Highland Park to the southeast; and Bedford–Stuyvesant to the south and southwest.
Hudson Valley Retreat & Departure
Head north out of the city. Visit the Old Dutch Church and the cemetery associated with Washington Irving’s headless horseman legend.
Sleepy Hollow
Sleepy Hollow is a village in Westchester County in the state of New York. It was one of the settings for Washington Irving's short story "The Legend of Sleepy Hollow".
Bear Mountain State Park
Bear Mountain State Park is in Rockland and Orange counties in New York, United States of America.
Woodbury Common Premium Outlets
Woodbury Common Premium Outlets is an outlet center located in the Central Valley section of Woodbury, New York. The center is owned by Premium Outlets, a division of Simon Property Group, and takes its name from the town in which it is located.
John F. Kennedy International Airport (JFK)
Aim to be back at the airport 3 hours before your flight. Give yourself plenty of time for the Belt Parkway traffic—it never sleeps.
- Download a parking app like SpotHero if you're driving in Manhattan; garage rates are eye-watering if you just pull in.