City Beautiful Tours

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NYC Five-Day Itinerary

landmarks, info and food suggestions

This itinerary serves as a checklist of must-see places in Manhattan. It highlights famous and hidden spots that are close to each other, allowing you to focus on one area of the city each day. After five days, you’ll have a good grasp of Manhattan’s diverse culture, architecture, and vibrant energy.

Each day is designed for easy walking within a specific section of the city. Feel free to mix, match, skip, or add locations as you see fit.

DAY 1: FIFTH AVENUE AND MIDTOWN HIGHLIGHTS

This is the most glamorous part of town, with major landmarks, fancy stores, and stunning eclectic architecture. One of the most famous streets in the world, Fifth Avenue runs through Midtown Manhattan and is synonymous with luxury shopping and historic landmarks.

What to see in Midtown Manhattan
  • ​The Plaza – An iconic “Old New York” historic hotel overlooking Central Park.
  • Tiffany’s – This world-famous jewelry store wasimmortalized by “Breakfast at Tiffany’s,” a classic film featuring Audrey Hepburn as Holly Golightly, a charming socialite who dreams of a glamorous life.
  • St. Thomas – A historic Episcopal church renowned for its Gothic Revival architecture and magnificent reredos.
  • Cartier Building – All glitz and glamour of the Gilded Age, this once-private home is now the flagship store of the House of Cartier.
  • St. Patrick’s Cathedral – A stunning example of Gothic Revival architecture and a functioning Catholic Cathedral, it’s a religious landmark and a New York cultural icon.
  • Rockefeller Center – A major NYC landmark, famous for its art deco architecture, ice skating rink, Radio City Music Hall, and the iconic Christmas tree during the holiday season.
  • Saks Fifth Avenue
  • Fred F. French Building
  • New York Public Library – A historic Beaux-Arts landmark, it is renowned for its vast collections of rare books, manuscripts, and historic artifactsand for its majestic architecture.
  • Grand Central Terminal – A Beaux-Arts Masterpiece renowned for its architectural grandeur, revolutionary design, and staggering statistics.
  • The Chrysler Building – With its glistening spire and glorious triangle-shaped crown, this iconic Art Deco skyscraper is one of the finest buildings in the world.
  • The Empire State Building – A symbol of New York City’s skyline and one of the greatest engineering achievements in the world, the Empire State Building broke records as the tallest in the world, the first to have more than 100 stories, and the one to be constructed in a record time of one year and forty-five days.
  • Theater District and Times Square, with their bustling atmosphere, Broadway theaters, and dazzling billboards, are among the most visited and recognizable locations in New York City.
  • Bryant Park is a lovely urban oasis located right behind the New York Public Library. Seasonal events include free music and dance performances, outdoor movie nights, and artisanal markets.
Where to eat in Midtown Manhattan

Here are a few suggestions for food stops in the area.

  • Grand Central Food Court – In one of the most iconic NYC locations, you can find a wide variety of food options, from quick snacks to tasty meals in cafe settings.
  • Oyster Bar at the Grand Central – The oldest restaurant in Grand Central, it’s well-known for its unique ambiance, vaulted Guastovino ceilings, and a menu featuring over 25 different varieties of fish, oysters, and shellfish.
  • Tartinery Café – Bar | Olympic Tower – This casual and very tasty café-bar serves bountiful salads, grain bowls, pastries, craft coffee, fresh juices, and smoothies from breakfast to dinner. It is hidden in the courtyard of the Olympic Tower, right by St. Patrick’s Cathedral.
  • DUOMO 51 – This upscale Italian restaurant features a terrace with the views of St Patrick’s Cathedral. During the summer and spring months, the terrace transforms into a green oasis reminiscent of the Toscana region of Italy.
  • Restaurant Row is a stretch of West 46th Street between 8th and 9th Avenues known for its diverse selection of restaurants within walking distance of Broadway theaters.
  • Swing 46 is a lively jazz club and restaurant located on Restaurant Row. It offers live music performances every night, great food, a dance floor, and a vintage-inspired atmosphere that evokes the spirit of the Swing Era.
  • John’s of Times Square bills itself as the most unique pizzeria in the world. It’s located in the old Gospel Tabernacle Church, and pizzas are made to order in 800-degree coal-fired brick ovens.
  • Carnegie Diner & Cafe is a classic American diner known for its nostalgic ambiance and extensive New York diner-style menu.
  • Gallaghers Steakhouse is a historic steakhouse located in Midtown Manhattan, celebrated for its classic steakhouse fare, aged beef, and old-world charm since 1927.
  • Marseille is Hell’s Kitchen’s quintessential French brasserie enjoyed by locals, theater enthusiasts, performers, and tourists alike.

Tours to take in Midtown Manhattan

Grand Central Terminal’s Secrets: A Self-Guided Audio Walking Tour
NYC Grand Central

Grand Central Terminal is one of the world’s top ten tourist attractions, filled with hidden features and fascinating stories. It’s also the setting for hundreds of famous films and novels, from Hitchcock’s North By Northwest to Salinger’s Catcher In The Rye.

“Welfare Island”: Roosevelt Island from the Tramway to FDR State Park
NYC Roosevelt Island

Discover the fascinating history of Roosevelt Island, from a sliver of farmland off of Manhattan to the home of New York City’s unwanted: prisoners, the mentally ill, and those with contagious diseases. On this walking tour, I’ll show you the island’s southern end where I’ll unpack some of its complicated 400-year-long history.

​​DAY 2: DOWNTOWN/FIDI – WALL STREET AND THE FINANCIAL DISTRICT

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—as well as the World Trade Center.

What to see in Financial District
  • Oculus is a striking transportation hub and shopping mall designed by Spanish architect Santiago Calatrava. It is known for its futuristic design, spacious interior, and symbolic role in revitalizing the area after the September 11 attacks.
  • 9/11 Memorial is a poignant tribute located at the World Trade Center site, commemorating the lives lost in the September 11, 2001 attacks.
  • World Trade Center – New World Trade Center Complex built after the devastation of 9/11
  • World Financial Center is a complex of office buildings and retail spaces. It features stunning views of the Hudson River, a beautiful glass atrium called the Winter Garden, upscale shops, dining options, and outdoor spaces, making it a vibrant destination for both business and leisure.
  • The Statue of Liberty is the universal symbol of freedom and democracy, located on Liberty Island in New York Harbor.
  • Charging Bull is an iconic bronze sculpture located near Bowling Green Park, symbolizing financial might of Wall Street.
  • Trinity Church is a historic Episcopal church located at the intersection of Wall Street and Broadway, known for its Gothic Revival architecture and an 18th century churchyard with the graves of such notable figures as Alexander Hamilton.
  • New York Stock Exchange is the world’s largest stock exchange by market capitalization and a symbol of global finance and economic power.
  • ​Federal Hall is a historic site where the first offices of the American government were located, and George Washington took the oath of office as the first President of the United States.
  • Wall Street is the historic heart of New York City’s Financial District, renowned for its role as a global financial hub and home to the New York Stock Exchange.
  • Brooklyn Bridge is the famous suspension bridge connecting Manhattan and Brooklyn, renowned for its revolutionary architectural design and panoramic views of the New York City skyline.
  • South Street Sea Port is a historic district featuring cobblestone streets and 18th-century buildings offering a charming glimpse into New York City’s maritime past.
  • Federal Reserve – Looking impregnable, the Federal Reserve building contains the most unusual vault that holds approximately 7,000 tons of gold bullion
  • St. Paul’s Chapel is New York City’s oldest public building in continuous use and Manhattan’s oldest surviving church. It is notable for its historic significance as George Washington’s place of worship and its role as a relief center after the 9/11 attacks.
  • The Woolworth Building is a spectacular neo-Gothic edifice dubbed the “Cathedral of Commerce.” One of the most magnificent skyscrapers, it stood the tallest in the world from 1913 to 1930.
  • New York City Hall is one of the oldest continuously operated city halls in the nation and still houses its original governmental functions.
  • The Municipal Building is one of the few monumental skyscrapers of the early part of the Twentieth Century and one of the largest government office buildings in the world. It was inspired by the Roman Arch of Constantine and the Palazzo Farnese in Rome.
Where to eat Downtown/Financial District

There’s an abundance of options available! Depending on your schedule and preferences, you can opt for unique historic restaurants or incredible food courts offering a wide array of choices.

  • ​Fraunces Tavern is a historic tavern known for its role in American history as a place where George Washington gave the farewell dinner after the victory in the Revolutionary War. The food and the ambiance are both fantastic
  • Delmonico’s is a historic fine dining establishment that has a distinction of being the first restaurant in America and the birthplace of Egg Benedict.Stone Street is a charming cobblestone street (the first paved street in New York!) lined with historic buildings that house lively restaurants and bars. The street’s vibrant atmosphere is ideal for dining and socializing.
  • Stone Street is a charming cobblestone street (the first paved street in New York!) lined with historic buildings that house lively restaurants and bars. The street’s vibrant atmosphere is ideal for dining and socializing.
  • Eataly NYC Downtown is a vibrant Italian marketplace offering a wide array of gourmet Italian food products, cafes, and restaurants in a bustling, market-style setting with views of the World Trade Center.
  • Tin Building is a historic structure that used to be a fish market but was turned into a fantastic food court. It’s located steps ay from the Brooklin Bridge which means that one can get the food to go and enjoy it “al-fresco” enjoying sweeping views.
  • Kokos at Pearl Alley at Pier 17 is a waterfront entertainment and dining destination, offering stunning views of the East River and Brooklyn Bridge.

Tours to take in THE FINANCIAL DISTRICT

NYC Battery Park
The Battery: NYC origins from Bowling Green Park to Stone Street

From a humble dirt-walled fort and trading outpost protected by artillery batteries, to the center of one of the most powerful cities on earth, The Battery is where it all began for New York. On this walking tour, I’ll show you around and share a few amazing stories, like how one of today’s most valuable islands, Manhattan, was bought for a handful of beads.

NYC Hamilton
History of Alexander Hamilton in New York: A Walking Tour with Context

See New York City’s evolution through the eyes of one of its most famous and influential citizens, Alexander Hamilton, often called “the architect of the American financial system”. On this walking tour with Context Travel expert, Ben Rubin, you’ll explore the city’s colonial and revolutionary history, walking in the shoes of Alexander Hamilton and his colonial neighbors.

DAY 3: UPPER EAST SIDE – CENTRAL PARK AND MUSEUM MILE, METROPOLITAN MUSEUM OF ART

This is the day to visit some of the best museums in the world, enjoy the tranquility of the Upper East Side neighborhood and, of course, stroll around Central Park.

What to see on the Upper East Side
  • Pulitzer Fountain depicts Pomona, the Roman goddess of fruitful abundance, and has unbelievable history
  • Central Park – the First Landscaped Public Park in the Nation is entirely man-made.
    • Bethesda Fountain and Terrace – One of the most photographed locations in the City, this iconic spot features the beautiful fountain known as the Angel of the Waters.
    • The Mall and Literary Walk – A wide, tree-lined promenade that leads up to Bethesda Terrace, known for its majestic American elms and statues of famous writers and poets.
    • Balto Statue – A bronze statue of the sled dog Balto, who led a team that delivered life-saving medicine during a diphtheria outbreak in Alaska.
    • The Lake – The Lake is a serene body of water where you can see rowboats and enjoy picturesque views.
    • The Reservoir – is the largest water body in Central Park. With stunning views, it’s been featured often on the silver screen.
    • Bow Bridge — Because of its low-lying and graceful curve, which resembles an archer’s bow, it’s widely considered a masterpiece of Victorian-era design.
    • Cleopatra’s Needle – An Egyptian Obelisk in Central Park.
  • The Carnegie Mansion – now the Cooper Hewitt Smithsonian Design Museum
  • Guggenheim Museum was established as the Museum of Non-Objective Painting. It’s famous for its collection and its building – a landmark work of 20th-century architecture.
  • Neue Gallery – a museum of early twentieth-century German and Austrian art.
  • Frick Collection – housing 1,100 works of art by Bellini, Titian, El Greco, Holbein, Rembrandt, and Vermeer, is currently regarded as one of the world’s greatest privately owned museums.
  • Metropolitan Museum – one the greatest Art Museums in the world, it’s an encyclopedic museum with over two million works in its permanent collection.
  • Fletcher House/Sinclair Mansion is one of New York City’s most impressive turn-of-the-century Gilded Age mansions.
  • Temple Emanu-El – is one of the largest synagogues in the world and one of the city’s preeminent architectural and religious landmarks.
  • The Sherry-Netherland Hotel Lobby – one of the most spectacular interior spaces in the city inspired by the Vatican Library by Raphael
Where to eat on the Upper East Side
  • Hot dogs from street vendors – Classic New York-style hot dogs are perfect for a fast and tasty bite while exploring the park.
  • Tavern on the Green – A historic restaurant offering American cuisine in a charming, fairy-tale setting. The outdoor seating area with a large patio wrapped in twinkling lights is especially lovely.
  • The Boathouse – A beautiful lakeside restaurant offering American cuisine. It’s a great place for a relaxing meal, with stunning views of The Lake and rowboats drifting by.
  • Café Sabarsky draws its inspiration from the great Viennese cafés that served as important centers of intellectual and artistic life at the turn of the century and offers a modern take on the culinary heritage of Austria.
  • Heidi’s House by the side of the road is a true neighborhood place with warm and quiet vibe and delicious food.
  • L’Osteria – Neighborhood Italian with dishes are inspired by the beauty of Italy, but also stand-out as something all their own.
  • The Penrose Bar – Inspired by old American and Cork traditions, this UES local serves locally sourced foods, well crafted brews, and drinks to please all.
  • Mission Ceviche –  A top ceviche restaurant in New York City specializing in authentic Peruvian cuisine.

Tours of the the UPPER EAST SIDE to take

NYC central park 1
Central Park Walk: The Mall, Bethesda Fountain, Strawberry Fields

Central Park isn’t just the most-visited urban park in the US. It’s home to Strawberry Fields, Poet’s Walk, and the most pampered trees in America. It’s also the backdrop of once-in-a-lifetime incidents like the Great Zoo Escape of 1874. This self-guided walking tour isn’t just a walk in the park, it’s a stroll through time with tales of love, loss, laughter, treachery and tragedy at every turn.

NYC Gilded Age 1
The Gilded Age Guide: Mansions of Fifth Avenue and Millionaire’s Row

Opposite New York’s Central Park is the world’s most prestigious address: Fifth Avenue, where you’ll find grand mansions built by Gilded Age robber barons and their heirs. And with outrageous fortune comes outrageous behavior. Hear extraordinary stories of love and loss, epic battles over status, and deliciously petty squabbles over the rules that governed society in the late 1800s.

DAY 4: NEIGHBORHOODS: GREENWICH VILLAGE, WEST VILLAGE, SOHO, LOWER EAST SIDE, CHINATOWN, LITTLE ITALY, GRAMERCY AND FLATIRON

Experience the magical parts of the city! Greenwich Village and the West Village neighborhoods are like stepping back into the first half of the 19th century, with charming streets that feel reminiscent of old England. SoHo stands out for its unique cast-iron architecture. Tranquil Gramercy offers a peaceful escape rarely explored by tourists, while Chinatown buzzes with vibrant smells and colors. End your day at the unique High Line Park and Hudson Yards, and ascend to The Edge – the highest outdoor sky deck in the Western Hemisphere.

CHINATOWN & LITTLE ITALY

Chinatown

  • The Bloody Angle – Doyers Street, a tiny street with a violent history.
  • Golden Buddha in the Mahayana Buddhist Temple
  • Nom Wah Tea Parlor – Vintage dim sum parlor serving food since 1920
  • Apotheke – Speakeasy inspired by European apothecaries and 19th-century Parisian absinthe dens. Dim lighting, Parisian-looking furniture, a gilded ceiling, and an imposing marble bar create a truly old-world feel.
  • Pings 22 Mott St offers an unforgettable experience of Hong Kong fare
  • Jing Fong 20 Elizabeth Street is one of New York’s premier dim sum and banquet halls
  • Joe’s Shanghai 46 Bowery is home to the signature Soup Dumplings. 
Little Italy Food with the side-order of History
  • Lombardi’s – the very first pizzeria in the U.S. and the birthplace of modern pizza
  • Ferrara Bakery – legendary cannoli since 1892

Little Italy movie locations

Mott street was a location for key scenes in Godfather I

  • Don Corleone is gunned down outside the Mietz Building, 128 Mott Street. In the movie, it’s Genco Olive Oil, Corleone’s business front.
  • Opposite, number 137 Mott Street, was the greengrocer stall at which Don Corleone buys oranges before being gunned down.

Elizabeth Street was a background for Godfather II

  • Joey Zasa is gunned down during the Italian-American street festival on Elizabeth Street.
  • Young Don Corleone follows Don Fanucci on the rooftops, the scene is a combination of 6th Street rooftops and a festival along Elizabeth Street.

Mulberry Street is featured in Godfather III

LOWER EAST SIDE and EAST VILLAGE
GREENWICH VILLAGE & WEST VILLAGE

Tours to take

NYC Bleeker Street
Bleecker Street Art Beat: A Pop Culture Journey from East to West Village

A walk from New York’s East to West Village is like embarking on a pop culture journey through the heart of Manhattan’s vibrant art scene. On this artistic and cultural adventure, you’ll trace the footsteps of iconic musicians like Taylor Swift and Bob Dylan, as well as cultural revolutionaries like Sarah Jessica Parker from Sex and the City, who helped to shape this part of the city.

SOHO

Tours to take

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SoHo: From Hell’s Hundred Acres to NYC’s cradle of art, a walking tour

New York City has a habit of tearing down beautiful old buildings to put up ugly new ones. On this walking tour, find out how SoHo escaped the wrecking ball and hear the remarkable stories of the colorful characters who saved this National Historic Landmark District.

GRAMERCY AND FLATIRON
  • Gramercy Park – the only private park in Manhattan
  • Tilden Mansion: Victorian Facade and Political Scandal
  • Block Beautiful—Mediterranean in Manhattan
  • The Church Missions House — from charity to photography
  • Pete’s Tavern – one of the oldest drinking establishments in the city, a great restaurant and the birthplace of O. Henry’s famous “The Gift of the Magi” story.
  • Dear Irving Speakeasy – the speakeasy featuring four rooms representing four different eras in history.
  • The Flatiron Building – one of the best known and most photographed buildings in New York
  • MetLife Tower – a Piece of Venice in New York
  • The Flatiron Room – Step into The Flatiron Room and find yourself transported to 1920s. You are about to experience a truly classy establishment with cocktails, jazz, and over 1000 variants of whiskey.
  • Eataly NYC Flatiron – a vibrant Italian marketplace with an array of restaurants, cafes and shops

Tours to take

NYC Gramercy and Flatiron 1
Textures of Two Neighborhoods: Tour of Gramercy and Flatiron Districts

The Flatiron District, located in the shadow of its glorious namesake, the Flatiron Building, is next to the enchanting Gramercy, a neighborhood that many tourists don’t get to see. On this walking tour, you’ll discover the Flatiron District’s breathtaking landmarks and experience the 19th-century charm of Gramercy.

DAY 5: UPPER WEST SIDE and HARLEM

These two neighborhoods, located on the West side of Central Park and to the north of it, are known for their amazing eclectic architecture, culture, history, landmarks, music, and an array of dining options, from cozy cafés to upscale eateries.

What to see on the Upper West Side and harlem
Where to eat on the Upper West Side
  • Cafe Lalo – With European design and open-air atmosphere, it‘s the place to see and to be seen. 
  • Zabar’s – This gourmet deli and grocer has been in the same location for over 85 years. Stop by their cafe for a bagel with whitefish
  • Miriam – Delicious Mediterranean
  • Bagels & Co. – Real New York bagels
Where to eat in Harlem
  • Sylvia’s – The most famous restaurant in Harlem serving authentic soul food sine 1962
  • Shrine – casual, cozy cafe and a great world music venue
  • Red Rooster – serves comfort food that celebrates the roots of American cuisine and the neighborhood’s diverse culinary traditions.

Tours to take

Tour OFFER copy
The Heart of Harlem: A Walk through 400 Years of History

Harlem’s unique culture has been shaped by its long and unusual history. On this walking tour through Central Harlem, you’ll hear stories about the artists, activists, and legends who made this neighborhood extraordinary. You’ll walk the same streets where Alexander Hamilton spent his final years, Langston Hughes wrote his poetry, and jazz greats like Duke Ellington, Ella Fitzgerald, and Louis Armstrong lived and performed.