The Ultimate New York Itinerary: 5 Days in the City That Never Sleeps

New York City is a whirlwind of skyscrapers, Broadway lights, and iconic neighborhoods—each with its own rhythm and flavor. But with so much to see, how do you experience and discovering the perfect New York itinerary for 5 days

After living in the city and exploring every corner, I’ve crafted the perfect New York itinerary that balances must-see landmarks with local secrets.

New York Itinerary: What to See & Do in 5 Days

Table of contents

• New York Itinerary: What to See & Do in 5 Days
• Best Time to Visit New York
• 5 Days New York Itinerary
• New York Itinerary: In Conclusion

Disclosure: Some links in this post are affiliate links. If you make a purchase through one of these links, we may earn a small commission (at no extra cost to you!). We're very grateful when you use our links to make a purchase:-).

Whether you’re a first-time visitor or a returning traveler, this guide covers:

• Iconic sights – Times Square, Central Park, Statue of Liberty
• Hidden gems – Secret rooftops, underground jazz bars, and Brooklyn’s best pizza
• Where to stay – Best hotels for every budget (with booking deals!)
• Pro tips – Navigating the subway, avoiding tourist traps, and saving money

Ready to dive in? Let’s make your New York itinerary unforgettable!

Best Time to Visit New York

The best time for your New York itinerary depends on your preferences:

• Spring (April-May): Cherry blossoms, mild weather, fewer crowds
• Fall (September-October): Crisp air, golden Central Park foliage
• Winter (December): Magical holiday lights and ice skating (but cold!)
• Summer (June-August): Festivals and rooftop bars (but hot and crowded)

Avoid: Late November (Thanksgiving crowds) and January-February (freezing temps).

5 Days New York Itinerary

This 5-day New York itinerary is designed to help you experience the magic of the Big Apple like a true New Yorker (with a little tourist flair). Let’s dive into the perfect blend of must-sees, hidden gems, and local eats that’ll make your NYC trip unforgettable.

Day 1: Manhattan Icons & Skyline Views

Your New York itinerary kicks off with the quintessential Manhattan experience—iconic skyscrapers, legendary food spots, and breathtaking skyline views. This carefully crafted day balances must-see landmarks with local secrets to help you experience the city like a true New Yorker.

Morning: Midtown Magic (7:30 AM - 12:00 PM)

7:30 AM – Breakfast at Ess-a-Bagel

📍 831 3rd Ave
Start your NYC adventure with what many consider the best bagel in the city. Must-try:

• Everything bagel with scallion cream cheese
• Bacon, egg & cheese on a sesame bagel (the NYC breakfast of champions)

Arrive before 8 AM to avoid the line that snakes around the block.

8:30 AM – Times Square (Before the Crowds Hit)

📍 42nd-47th St between Broadway/7th Ave
Experience the Crossroads of the World when it's (almost) peaceful:

• Snap photos with the Naked Cowboy (if he's there)
• Visit the TKTS booth to scope out same-day Broadway deals
• Peek inside Ripleys Believe It or Not if you're early

The red glass stairs above the TKTS booth offer the best elevated views.

10:00 AM – Top of the Rock Observation Deck

📍 30 Rockefeller Plaza

Why this beats the Empire State Building:

• You can SEE the Empire State in your photos
• Smaller crowds and timed-entry tickets
• Stunning 360° views of Central Park and downtown

Afternoon: Central Park & Culture (12:30 PM - 5:00 PM)

12:30 PM – Lunch at The Halal Guys

📍 53rd St & 6th Ave (Original cart)
Order like a local:

• Chicken & rice platter (ask for "white and hot sauce")
• Extra pita bread to soak up the legendary sauces

2:00 PM – Central Park Bike Tour

📍 Rentals at 56th St & 6th Ave
Must-see stops on your DIY tour:

• Bethesda Terrace (iconic fountain and tile ceiling)
• Bow Bridge (most photographed spot)
• Strawberry Fields (John Lennon memorial)

4:00 PM – Metropolitan Museum of Art Highlights

📍 1000 5th Ave
Skip the overwhelm with this 90-minute game plan:

1. European Paintings (Van Gogh, Monet)
2. Temple of Dendur (Instagram-famous Egyptian temple)
3. American Wing (Washington Crossing the Delaware)

Pro Move: Use the 81st St entrance for shorter lines.

Evening: Broadway & Skyline Cocktails (6:30 PM - 11:30 PM)

6:30 PM – Pre-Theatre Dinner at Sardi's

📍 234 W 44th St
The most iconic Broadway restaurant:

• Try their famous veal marsala
• Spot celebrity caricatures covering the walls
• Ask about Broadway gossip - the waiters know everything

8:00 PM – Broadway Show

Current top picks:
Hamilton (Lin-Manuel Miranda's masterpiece)
Moulin Rouge (Spectacular sets & pop hits)
The Lion King (Perfect for families)

Get TKTS same-day discounts at the Times Square booth.

11:00 PM – Nightcap at 230 Fifth Rooftop

📍 230 5th Ave
End your night with:
Hot apple cider cocktails (in winter)
Unbeatable Empire State views
Cozy igloos (October-April)

Pro Tips for Day 1

Walk everywhere - Midtown attractions are closer than they appear
Use the Curb app for yellow cabs (cheaper than Uber in this area)
Buy attraction tickets in advance to skip lines
Layer clothing - Temperatures vary between streets and observation decks

There's no better introduction to New York than standing atop Rockefeller Center as golden hour washes over the skyline, realizing every movie scene you've loved was right here - and now you're in it.

Need more city itineraries? Check out our 1-Week Chicago Itinerary for another urban adventure!

Day 2: Statue of Liberty & Downtown NYC

Your second day in New York dives into the city's historic heart, blending world-famous landmarks with downtown's edgy energy. This Statue of Liberty and Lower Manhattan itinerary maximizes your time while avoiding tourist traps.

Morning: Lady Liberty & Ellis Island (7:30 AM - 12:30 PM)

7:30 AM – Early Statue Cruise

📍 Depart from Battery Park

Why go early?

• Beat 90% of crowds
• Best morning light for photos
• Cooler temperatures

Ticket Options:

• Crown Access (Must book 3+ months ahead via Statue Cruises)
• Pedestal Access (Great views, easier to get)
• Reserve Only (Basic access, Trip.com)

Pro Route:

1. Ferry to Liberty Island (45 mins exploring)
2. Ferry to Ellis Island (Immigration Museum)
3. Return ferry with skyline views

The Statue's torch (not accessible) is visible in the museum!

Late Morning: Financial District (11:00 AM - 1:00 PM)

11:00 AM – Wall Street Highlights

📍 Walking Tour Route:

• Charging Bull (Rub the horns for luck)
• Fearless Girl (Feminist statue facing the bull)
• New York Stock Exchange (Free exterior photos)
• Federal Hall (George Washington inauguration site)

12:00 PM – Lunch at Fraunces Tavern

📍 54 Pearl St
Dine where Washington bid farewell to his troops:

• Shepherd's pie (Colonial-era recipe)
• Sam Adams ale (Revolutionary War favorite)

Afternoon: Tribeca & SoHo (1:30 PM - 5:30 PM)

1:30 PM – Oculus & 9/11 Memorial

📍 World Trade Center

• Oculus (Stunning white whalebone architecture)
• 9/11 Memorial Pools (Arrive weekdays for fewer crowds)
• Optional: One World Observatory (Skip-the-line tickets)

3:00 PM – SoHo Shopping & Secret Spots

📍 Start at Prince & Broadway

• Artist & Fleas Market (Local designers)
• Housing Works Bookstore (Hidden literary gem)
• Crosby Street Hotel (Grab tea in their secret garden)

Hit Reformation (eco-chic) and What Goes Around Comes Around (vintage Chanel).

Evening: West Village Magic (6:30 PM - 11:00 PM)

6:30 PM – Dinner at Carbone

📍 181 Thompson St
Reservations essential (Book 28 days out at 9 AM EST):

• Spicy rigatoni vodka (Legendary dish)
• Tableside Caesar salad

Can't get in? Try L'Artusi (amazing pasta) or Minetta Tavern (best burger).

8:30 PM – Comedy Cellar

📍 117 MacDougal St
How to experience it right:

• Arrive 1 hour early for standby
• Grab drinks at Downstairs Bar first
• Expect surprise celebrity drop-ins (Louis CK, Amy Schumer)

10:30 PM – Late-Night Jazz at Smalls

📍 183 W 10th St

• $20 cash cover (Open til 4 AM)
• Intimate underground vibe
• Jam sessions often with Juilliard students

Pro Tips for Day 2

• Walk everywhere – Downtown attractions are close
• Statue ferry includes all stops – don't pay extra
• Best Liberty photos from Battery Park before boarding
• Comedy Cellar is cash-only

Downtown NYC holds layers of history in every cobblestone – from Dutch settlers to Wall Street traders to the artists who made SoHo cool. Today, you'll walk through centuries in just a few blocks.

Extending your trip? Our 1-Week Chicago Itinerary offers another urban adventure!

Day 3: Brooklyn & Williamsburg

Cross the East River and discover why Brooklyn has become NYC's cultural heartbeat. This full-day Brooklyn itinerary blends iconic sights with Williamsburg's hipster haunts, giving you an authentic taste of NYC beyond Manhattan.

Morning: DUMBO & Brooklyn Heights (8:00 AM - 12:00 PM)

8:00 AM – Breakfast at Time Out Market

📍 55 Water St
Start at this food hall with:

• Bagels from Ess-a-Bagel outpost
• Clinton St. Baking Co.'s famous pancakes
• Brooklyn Roasting Company coffee

Pro Tip: Grab food to-go for picnic photos!

9:00 AM – Iconic Photo Ops

📍 Walking Route:

1. Washington Street (Perfect bridge framing)
2. Pebble Beach (Under the bridge)
3. Jane's Carousel ($2 rides with skyline views)

10:30 AM – Brooklyn Bridge Walk

Manhattan → Brooklyn route is better because:

• Skyline views ahead of you
• Ends near DUMBO's attractions
• Less crowded than Brooklyn→Manhattan

Insider Move: Stop at Pier 17 halfway for restrooms and water.

Afternoon: Williamsburg Cool (12:30 PM - 5:00 PM)

12:30 PM – Smorgasburg (Saturdays Only)

📍 90 Kent Ave (April-Oct)

Must-eat items:

• Ramen Burger
• Big Mozz sticks
• Mofongo from Peachy's

Weekday Alternative: Lunch at Lilia (Reserve 30 days out)

2:00 PM – Street Art & Shopping

📍 Williamsburg Highlights:

• Devoción Coffee (Lush Colombian coffee farm vibe)
• Artists & Fleas Market (Vintage Levi's, local jewelry)
• Sweatshop NYC (Cool Aussie-designed tees)

4:00 PM – Brooklyn Brewery Tour

📍 79 N 11th St

• $18 includes 3 tastings
• Learn about NYC's craft beer revolution
• Try the Sorachi Ace (cult favorite saison)

Evening: Sunset & Nightlife (6:00 PM - 11:30 PM)

6:00 PM – Sunset at Domino Park

📍 300 Kent Ave

• Walk the old Domino Sugar factory relics
• Best golden hour views of Manhattan

7:30 PM – Dinner at Llama Inn

📍 50 W 15th St
Peruvian fusion with:

• Octopus anticucho
• Pisco sour flights
• Rooftop seating available

9:30 PM – Nightcap at Night of Joy

📍 667 Lorimer St

• Retro cocktail lounge
• Live jazz Wednesdays
• $12 happy hour until 8pm

Pro Tips for Day 3

• Take the East River Ferry for scenic transport
• Best bridge photos at sunrise or weekdays
• Skip Grimaldi's - Juliana's Pizza is better
• Street art map available at Brooklyn Tourist Info

Brooklyn isn't Manhattan's sidekick anymore - it's where artists brew beer in old factories, where every brick wall holds street art secrets, and where the Manhattan skyline becomes your backdrop rather than your world.

Love urban exploration? Our 1-Week Chicago Itinerary delivers another vibrant city guide!

Day 4: Uptown & Harlem

Your New York itinerary takes a soulful turn today as you explore Uptown Manhattan and Harlem, where jazz history, world-class museums, and legendary food scenes collide. This carefully crafted day balances iconic attractions with authentic local experiences you won't find in typical guidebooks.

Morning: Museum Mile & Central Park North (8:30 AM - 12:30 PM)

8:30 AM – Breakfast at Jacob's Pickles

📍 509 Amsterdam Ave
Fuel up Southern-style for your Uptown adventure:

• Biscuit sandwiches (try the fried chicken version)
• Maple bacon lollipops
• Spiked cold brew coffee

10:00 AM – American Museum of Natural History

📍 Central Park West at 79th St
Must-See Highlights (90-Minute Game Plan):

1. Milstein Hall of Ocean Life (The giant blue whale)
2. Rose Center for Earth & Space (Cosmic Pathway)
3. Dinosaur Halls (T. rex & Titanosaur)

Use the 81st St entrance to avoid crowds. Book tickets via WayAway.

12:00 PM – Central Park North Exploration

📍 Lesser-known park gems:

• The Pool (Serene waterfall area)
• Hudson River overlook at 110th St
• Marcus Garvey Park (Local hangout with great skyline views)

Afternoon: Harlem Renaissance (1:30 PM - 5:00 PM)

1:30 PM – Sylvia's Legendary Soul Food Lunch

📍 328 Malcolm X Blvd
Order like a regular:

• Fried chicken & waffles
• Smothered pork chops
• Sweet tea by the gallon

Insider Move: Visit the Sylvia's Store for soul food spices to take home.

3:00 PM – Harlem Cultural Walk

📍 Must-Visit Spots:

• Apollo Theater (See the "Tree of Hope" performers touch)
• Studio Museum Harlem (Cutting-edge Black art)
• Strivers' Row (Historic architectual gems)

4:00 PM – Red Rooster Cocktail Hour

📍 310 Malcolm X Blvd
Marcus Samuelsson's hotspot for:

• Obama's favorite chicken wings
• Live jazz on weekends
• People-watching from the sidewalk tables

Evening: Jazz & Supper Clubs (6:30 PM - 11:00 PM)

6:30 PM – Dinner at Melba's

📍 300 W 114th St
Harlem's modern soul food queen:

• Eggnog french toast (Yes, for dinner!)
• Mac & cheese with crab meat

8:30 PM – Jazz at Minton's Playhouse

📍 206 W 118th St
Where bebop was born:

• $20-40 cover (Reservations recommended)
• Intimate 50-seat setting
• Late-night jam sessions

Alternative: Shrine Harlem for more eclectic live music.

Pro Tips for Day 4

• Take the A/C/B/D trains - Best for Uptown access
• Sunday gospel brunches are Harlem's signature (if your New York itinerary includes a weekend)
• Hamilton Heights has stunning brownstones for photos
• Soul food portions are huge - Share plates

Harlem isn't just a neighborhood - it's a living museum of Black excellence, where Langston Hughes' poetry still whispers through brownstones and every jazz note carries centuries of history.

Extending your trip? Our 1-Week Chicago Itinerary offers another urban adventure!

Day 5: Queens & Hidden NYC

Your New York itinerary concludes with an exploration of Queens—the city’s most diverse borough—and a few Manhattan secrets most tourists miss. This day is packed with underrated gems, authentic global cuisine, and skyline views even locals don’t always know about.

Morning: Flushing’s Chinatown & Cultural Wonders (8:00 AM - 12:30 PM)

8:00 AM – Breakfast at Nan Xiang Xiao Long Bao

📍 39-16 Prince St, Flushing

Why it’s special:

• Soup dumplings ranked among NYC’s best
• Watch chefs hand-fold dumplings through the kitchen window

Order like a pro:

• Pork XLB (xiao long bao)
• Scallion pancake
• Hot & sour soup

Insider Tip: Arrive by 7:30 AM on weekends to avoid the infamous line.

9:30 AM – Queens Museum & Unisphere

📍 Flushing Meadows Corona Park

Must-see highlights:

• Panorama of NYC (The world’s largest scale model of the city)
• 1964 World’s Fair relics (Including the iconic Unisphere)
• Tiffany glass collection

Rent a Citi Bike to explore the park’s hidden corners.

Afternoon: Long Island City & Secret Manhattan (1:00 PM - 5:30 PM)

1:00 PM – Lunch at Casa Enrique

📍 5-48 49th Ave, LIC

NYC’s only Michelin-starred Mexican spot:

• Chiles en nogada (Stuffed poblano peppers)
• Duck carnitas tacos
• Horchata ice cream

2:30 PM – LIC Waterfront & Hidden Views

📍 Walking Route:

1. Gantry Plaza State Park (Best Manhattan skyline photos)
2. Hunter’s Point South Park (Secret sunset spot)
3. The Cliffs at LIC (Free rock climbing with skyline views)

4:00 PM – Roosevelt Island Tram Adventure

📍 59th St & 2nd Ave

Why it’s worth it:

• Same MetroCard fare as subway ($2.90)
• Stunning aerial views of the East River
• Great photos from the island’s lighthouse

Evening: Hidden Manhattan & Farewell Drinks (6:30 PM - 11:00 PM)

6:30 PM – Dinner at Russ & Daughters Café

📍 127 Orchard St, Lower East Side

NYC’s most iconic Jewish appetizing store:

• Classic bagel & lox
• Matzo ball soup
• Egg cream soda

8:30 PM – Speakeasy Hopping

Secret bars most tourists never find:

• Attaboy (No menu – they craft based on your mood)
• Please Don’t Tell (Enter through phone booth at Crif Dogs)
• The Back Room (1920s gangster hideout)

10:30 PM – Final Skyline View at The Edge

📍 Hudson Yards

Why end here?

• Less crowded than Empire State
• Open latest (until midnight)
• Glass floor 1,100 feet up

Book timed tickets: WayAway

Pro Tips for Day 5

• 7 train = The International Express (Passes through Little India, Thai Town, etc.)
• Download "Queens Eats" app for authentic ethnic food maps
• Roosevelt Island tram runs 24/7 – Great for late-night city views
• Flushing food courts (New World Mall, Golden Shopping Mall) are culinary wonderlands

Queens doesn’t just welcome the world—it serves the world on a paper plate, from Tibetan momo dumplings to Colombian arepas, all with a side of unbeatable skyline views. This is the New York tourists rarely see but locals cherish.

Loved this urban adventure? Our 1-Week Chicago Itinerary delivers another incredible city guide!

New York Itinerary: In Conclusion

This 5-day New York itinerary packs in the best of the city—from skyline views to underground jazz bars. Whether you’re here for the food, culture, or iconic sights, NYC never disappoints.

---

Want another urban adventure? Check out our 1-Week Chicago Itinerary next!