5 days in New York sightseeing itinerary

Manhattan is a tapestry of neighborhoods with very different look and feel. Fifth Avenue divides Manhattan into West Side and East Side. Downtown lies below 14th Street, Midtown stretches from 14th to 59th Streets, and Uptown is everything above 59th Street. In this itinerary, each day is devoted to a section of the city that's easy to do on foot.

​Day 1: Fifth Avenue and Midtown Highlights (Midtown)

All the sights here are located along or close to Fifth Avenue. This is the most glamorous part of town with major landmarks, fancy stores and beautiful architecture. 

• ​Rockefeller Center -- a City Within a City
• St. Patrick’s Cathedral  -- one spectacular folly!
• The Plaza  -- Where Nothing Unimportant Ever Happens
• Cartier Building — a  Pearl of Fifth Avenue
• St. Thomas — Medieval Church on 5th Avenue
• Grand Central Terminal — a Beaux-Arts Masterpiece
• The Chrysler Building  —  The most spectacular Art Deco silhouette in the city 
• The Empire State Building  —  The Eighth Wonder of the World saved by a Hollywood movie
• New York Public Library  -- Lions, books, and philanthropy
• Saks Fifth Avenue — “a Guarantee of High Style”
• The St. Regis -- What do Napoleon, Dalí and Marilyn Monroe have in common?
• Fred F. French Building  -- “Mesopotamian” in Manhattan
• Tiffany's -- Tiffany Blue
• Bryant Park  -- The location of the first American World Fair
• Theater District and Times Square — the Crossroads of the World in a shape of a bowtie

​Day 2: Wall Street and the Financial District (Downtown/FIDI)

This is the most historic part of town, the city started here in the 17th century as a Dutch colony called New Amsterdam. This is where the American Revolution was brewing and where the first institutions of the new republic were located. This is the location of world-renown Wall Street - the financial center of the world. Adjacent to the area are colorful neighborhoods of Chinatown and Little Italy.

• Wall Street  -- a tiny street with a big history
• New York Stock Exchange  — a Roman temple with glass walls
• Castle Clinton  -- the first immigration station
• St. Paul’s — a Chapel Older than the United States
• Federal Hall — over 300 years of American History
• Charging Bull  — One Giant Christmas Present
• Trinity Church  — on Wall Street since 17th century
• Brooklyn Bridge — The oldest and the most beautiful
• The Municipal Building — a Beaux-Arts Skyscraper
• Statue of Liberty  — an American Colossus​
• New York City Hall — one of the oldest continuously operated city halls in the nation
• The Woolworth Building -- “Cathedral of Commerce”
• Fraunces Tavern — Where George Washington gave a farewell dinner for his officers
• South Street Sea Port 

Day 3: Old New York: Greenwich Village, West Village, SOHO(Downtown), and Gramercy and Flatiron neighborhoods (Midtown)

Magical parts of the city! Walk around Greenwich Village / West Village neighborhoods, pretty much frozen in the first half of the 19th century. You will not see skyscrapers here, instead, it'll feel like visiting good old England. Visit SoHO for its cast-iron palaces. Walk north to see Gramercy - rarely visited by tourists, and Flatiron to admire the Flatiron building. You could finish your day with visiting unique High line Park and Hudson Yards - a new $25 billion development featuring the Edge - the highest outdoor sky deck in the Western Hemisphere.

• Washington Square Arch  —  a Triumphal Arch and a Small Revolution
• 17 1/2 Bedford street  — the narrowest house in New York
• Grove Court  — a setting for O.Henry's story​
• Gramercy Park  — the only private Park in Manhattan 
• Pete's Tavern  — the oldest bar in New York 
• Flatiron Building — one of the most beloved New York silhouettes​ ​

​Day 4: Central Park and Museum Mile, Metropolitan Museum of Art (Upper East Side)

Walk through the Central Park and try not to get lost! The Park is huge, and you can spend quite a lot of time meandering through its 60 miles of pedestrian paths, constantly discovering new vistas. Along the Park on its East Side is a stretch of Fifth Avenue called the Museum Mile, lined with Gilded Age robber barons' mansions and hosting 11 museums. It would be a good time to visit some of them, but if you only have time for one, it would be the Metropolitan Museum of Art.

• Central Park  — the first landscaped park in America 
• Tavern on the Green -- an iconic New York restaurant in the park 
• A Boathouse  — another historic restaurant with a view to the lake with an option of renting a boat
• Bethesda Terrace — one of the most picturesque places in New York 
• The Reservoir 
• Frick Collection — the house built to be a museum
• Neue Gallery — Grace Vanderbilt’s “Gardener’s Cottage”
• Guggenheim Museum — A unique museum building 
• Metropolitan Museum — One of the premier world's museums with the collections spanning 6 thousand years of human history

​Day 5: Upper West Side - Lincoln Center, Dakota, St John the Divine (Upper West Side)

Here you'll see the  famous Lincoln Center - home of the Metropolitan Opera. Walking thought the neighborhood, you'll see some of the most fascinating buildings, like Parisian Ansonia and castle-like Dakota. If you venture further uptown, you'll be able to see the grandiose Riverside Church and St. John the Divine, arguably, the largest cathedral in the world, spectacular but still unfinished.

• Columbus Circle
• Lincoln Center 
• The Ansonia Building -- A Parisian vision on the streets of New York
• The Dorilton  -- One Beautiful Aberration
• Dakota — The Most Famous Apartment Building in New York City
• The San Remo — The Aristocrat of Central Park
• Museum of Natural History 
• St John the Divine  -- The Cathedral that was never finished
• Riverside Church