New York City Itinerary 5 days

Planning your first time in New York City? This 5-day itinerary packs the best things to see, do, and eat—without feeling overwhelming. I’ve lived here and used my experience to design a perfect itinerary that balances iconic sights, hidden gems, and strategic planning so you can squeeze in more.

Each day’s itinerary starts with a summary in a yellow box for a quick view, and you can grab the free PDF download by joining The Wanderbug mailing list.

From historic sights like the Statue of Liberty to best restaurants and lively bars, this guide covers it all. Spend a day exploring Brooklyn, catch recommended shows, and dive into NYC’s best neighbourhoods—whether it’s the charm of West Village, the buzz of SoHo, or the energy of Midtown Manhattan. Whether you’re here for ticketed experiences or just to wander, this plan ensures you don’t miss a thing.

DAY1: New York City Itinerary: 5 Days of Iconic Adventures

Start your NYC adventure with art, parks, and Broadway magic – a perfect first day mixing culture and excitement.

Morning at The Met: Where History Comes Alive

Begin your day at The Met, one of the largest museums in the world. Don’t try to see everything – instead, focus on sections like the stunning Egyptian Art with its temples, the grand Medieval Art Great Hall, or classical Greek and Roman art. For the best experience, book a guided tour and end with breathtaking views from The Roof overlooking Central Park’s treetops.

Lunch Break: Upper East Side Flavors

Refuel at cozy The Penrose for classic American bar fare or Saint Ambroeus on Madison Avenue for a taste of Milan. If you prefer science over art, the nearby American Museum of Natural History makes a great alternative.

Afternoon Stroll: Central Park’s Hidden Gems

Discover why Central Park is NYC’s most beautiful escape. Follow this tourist trail: from the Jacqueline Kennedy Onassis Reservoir (magical during Spring cherry blossoms) to the romantic Bow Bridge and iconic Bethesda Fountain. Don’t miss the Boathouse by Central Park Lake – it’s pure New York charm.

Broadway Night: Dinner & Show Magic

No first visit is complete without a Broadway show – 2025’s hottest include Hamilton, Wicked, or The Lion King. Grab tickets on TicketMaster, then dine at The Terrace & Outdoor Gardens near Times Square (a hidden gem among tourist trap restaurants). Pro tip: make reservations early for this Theater District favorite!

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Day 2: Exploring Downtown Manhattan’s Chic Neighborhoods & Nightlife

Discover the fashionable West Village, artsy SoHo, charming Nolita, and an unforgettable immersive theater experience

Morning in the West Village: NYC’s Most Charming Neighborhood

Start your day wandering the leafy streets of the West Village, where brownstones and cozy cafes create a storybook setting. Walk down to Washington Square Park to see street performers beneath the iconic arch. For brunch, you can’t go wrong at either Jack’s Wife Freda (try their famous rosewater waffles) or Joseph Leonard for classic American fare with a gourmet twist.

Afternoon Exploration: SoHo’s Cast Iron District & Nolita’s Hidden Gems

Head downtown to SoHo, where cast iron facades along Greene St and Mercer Street showcase NYC’s architectural heritage. Pop into contemporary galleries like Jeffrey Deitch, then shop at the MoMA Design Store for unique souvenirs. Cross into Nolita for the city’s best pizza at Prince Street Pizza and save room for Milk Bar’s legendary banana pudding or Van Leeuwen’s artisanal ice cream.

Evening Adventure: The High Line & Sleep No More Experience

As evening falls, explore the Meatpacking District, where cobblestone streets meet trendy lounges. Walk the High Line, an elevated railway transformed into a stunning public garden. Dine at Pastis for classic French bistro fare before the main event: Sleep No More, an immersive theater adaptation of Macbeth set in the McKittrick Hotel. You’ll chase actors through a four-storey set – unlike any traditional theater experience.

Day 3: Brooklyn Bridge to Williamsburg – The Best of Brooklyn

From iconic landmarks to hipster havens, discover why Brooklyn deserves a full day

Morning: Iconic Views & Cobble Hill Charm

Begin at the Financial District to walk across the Brooklyn Bridge at sunrise for breathtaking iconic views. In Dumbo, snap that perfect bridge photo, then grab breakfast at Time Out Market. Head to Cobble Hill to browse Books Are Magic, the beloved bookstore owned by author Emma Straub, and pick up picnic supplies from Bien Cuit bakery.

Afternoon: Prospect Park & Botanical Bliss

Enjoy your picnic in Prospect Park, Frederick Law Olmsted’s other masterpiece. The adjacent Brooklyn Botanic Garden is especially magical during cherry blossom season. Rent a paddleboat on the lake or simply relax under ancient trees.

Evening: Williamsburg’s Hipster Paradise

As night falls, head to Williamsburg for rooftop cocktails at Westlight, offering panoramic Manhattan views. For dinner, Maison Premiere serves the freshest oysters with absinthe cocktails, while Misi offers life-changing pasta (don’t miss their sheep’s milk ricotta occhi). End your night dancing at a local music venue or sipping craft cocktails at a speakeasy.

Alternative Option:

For sports fans, catch a Yankees game at the historic Yankee Stadium or see the Knicks play at Madison Square Garden – both quintessential NYC experiences.

Day 4: Immigrant History & East Village Nightlife

Taste your way through the Lower East Side’s culinary history, then experience NYC’s legendary comedy scene

Morning: Tenements & Tastes Tour

The Urban Adventures Tenements, Tales & Tastes Tour brings immigrant history to life through food. You’ll sample authentic Jewish deli fare at Russ & Daughters, classic pastrami at Katz’s Delicatessen, and other ethnic specialties while learning about the neighborhood’s transformation.

Afternoon: Tenement Museum & Rooftop Views

At the Tenement Museum, choose an Apartment Tour to step inside perfectly preserved immigrant homes from different eras. History buffs will love the “Hard Times” tour focusing on the Great Depression. For contemporary contrast, head to Mr Purple’s rooftop for cocktails with downtown views.

Evening: Comedy & Cocktails

Start your East Village bar crawl at Death & Co for artisanal cocktails, then experience NYC’s oldest pub at McSorley’s Old Ale House (they only serve light or dark ale!). Cap the night at Comedy Cellar, where you might spot famous comedians trying new material (tickets around $22, plus drink minimum).

Dinner Options:

• Via Carota: West Village’s perfect pasta
• Dante: World’s best bar (2019) with incredible negronis
• Employees Only: Speakeasy vibe with killer cocktails

Day 5: Classic NYC – Museums, Skyscrapers & Jazz

Experience the essential New York with iconic museums, breathtaking views, and smooth jazz

Morning: Art & Architecture

Choose between the newly renovated MoMA (book timed tickets to avoid crowds) or the intimate Morgan Library, home to original Mozart manuscripts and a breathtaking private library. Both offer completely different but equally New York experiences.

Afternoon: Grand Central & Bryant Park

Grab lunch at Ess-A-Bagel (the everything bagel with scallion cream cheese is life-changing), then explore Grand Central Station. Don’t miss:

• Whispering Gallery’s acoustic magic
• The constellation ceiling in the main concourse
• Oysters at the historic Grand Central Oyster Bar
• A cocktail at The Campbell, a 1920s-era hidden bar

Evening: Skyline Views & Smooth Jazz

For sunset, choose:

• Top of the Rock: Best overall skyline views (including the Empire State)
• Empire State Building: The classic experience (more romantic)

End your NYC adventure with live jazz at Village Vanguard, where legends like Miles Davis played, followed by a late dinner at Minetta Tavern (their black label burger is famous for good reason).

This version maintains all your keywords while providing richer descriptions and better flow between sections. Each day has a clear narrative arc while still packing in all the essential details.