Planning a trip to New York City? Whether it’s your first time or your fifth, this 5-day itinerary blends the must-see icons, unforgettable food, and local favourites that make the city so addictive. From Central Park mornings to Brooklyn sunsets, from hotdogs on the corner to pastrami at Katz’s, this guide will help you experience NYC like I love to do it.
✨ Introduction
New York City is one of those places I never get tired of. It’s chaotic, glamorous, exhausting, and inspiring all at once. Each visit feels different, because the city always has a way of surprising you – with new corners, flavours, and little magical moments.
I’ll take you through the itinerary first (I always hated scrolling forever before finding the main thing 😉). At the end, you’ll also find tips, hotel finds, and ticket links. Some are affiliate links, but you don’t pay anything extra – these are genuine picks I choose for myself and my family.
Here it goes:
Day 1 – Central Park, Midtown & a Hotdog 🌭
Start your trip with a slow morning wander through Central Park. Grab a bagel with cream cheese (because, New York! = we even got rainbow bagels!) and a steaming cup of Starbucks coffee on the way in. I used to hate Starbucks but I learned to love it – especially seasonal drinks; and drinking this in New York is… well, a classic.
Let yourself get lost for a while — cross the iconic Bow Bridge, stop at Bethesda Terrace, and watch the rowboats drift across the lake. It’s the perfect way to ease into the rhythm of the city.
From there, make your way south into Midtown Manhattan:
- Times Square — yes, it’s touristy, but it’s also dazzling chaos, and no first-time trip to New York feels complete without standing under those neon billboards. Time for a selfie!
- Empire State Building — one of the city’s most iconic landmarks. Ride the elevator up for panoramic views that stretch across Manhattan and beyond (we actually went at sunset and it was breathtaking, but any time of day is good – just watch out for the wind!).
- 5th Avenue — stroll past designer shops and glitzy displays. Even if you’re not buying (if you can resist it!), it’s worth it for the spectacle.
When hunger hits again, keep it classic: grab a hotdog from a street cart. That’s a must. Funny story; I have a friend that turned vegetarian – meat-eater because of the New York hot dog!
Stand on the corner with mustard dripping onto your napkin, taxis honking as they zip past, and you’ll feel like you’ve stepped into a New York movie.
For the evening, end on a high note — a Broadway show. Whether you choose a timeless classic or the latest hit, there’s nothing like the magic of Broadway lights and live performance in the heart of the city. We went for the classic Lion King and we were blown away! I’d go again in a second, even for the same show.
Day 2 – Museums & the Upper East Side
Dedicate this day to New York’s world-class art and history. Begin at the Metropolitan Museum of Art, a place so vast you could spend a week inside and still not see it all. Wander from Egyptian temples to Impressionist paintings, from medieval armor to delicate Japanese scrolls. Don’t rush — part of the magic here is allowing yourself to get lost among the treasures.
If you’d like to split your time, head a little further up Museum Mile to the Guggenheim Museum. Frank Lloyd Wright’s spiral masterpiece of a building is an artwork in itself, and the rotating exhibitions of modern and contemporary art make it a must. It’s always difficult for me and my husband to decide; he loves history and I love modern art… So we just do both!
At some point, step outside for a breather. Stroll down Museum Mile, soaking in the elegance of the Upper East Side (Gossip Girl vibes), or cross into Central Park again and enjoy a pretzel from a street vendor on a bench under the trees. It’s the perfect reminder that New York is both grandeur and simplicity, side by side.
For dinner, trade soaring museum halls for something more intimate: a cozy Upper East Side bistro. Imagine flickering candlelight, wine poured into heavy glasses, and comfort food served with quiet sophistication. It’s the contrast that makes New York so unforgettable – high culture by day, warm neighbourhood charm by night.
Day 3 – Downtown, the Statue & Katz’s Deli 🥪
Start your morning on the water: take the ferry to visit the Statue of Liberty and Ellis Island. No matter how many times you’ve seen her in photos or movies, standing at the base of Lady Liberty feels moving and powerful. At Ellis Island, walk through the halls where millions of immigrants first arrived — it’s history that feels alive.
In the afternoon, head back into the Financial District. Wander down Wall Street, snap a photo with the Charging Bull (touch his hmmm for financial luck!), and then take time at the 9/11 Memorial & Museum. The reflecting pools are striking in their silence, a place where the city slows down and remembers. Not being American this memorial really struck us, no matter where you’re from, we will always remember that day.
Before the day fades, make a detour to the Lower East Side for a foodie pilgrimage: Katz’s Delicatessen. Order the legendary pastrami on rye — stacked so high it feels impossible to bite into. Smoky, juicy, and dripping with flavour, it’s the sandwich that defines New York. There is usually a long waiting line but so worth it! It’s an experience by itself (foodie heaven!).
As the evening sets in, walk across the Brooklyn Bridge at sunset. The cables glow golden in the fading light, the skyline begins to sparkle, and you’ll understand why this walk is considered one of the most unforgettable experiences in New York. Time to take those Instagram worthy photos again!
Day 4 – Brooklyn Vibes
Trade Manhattan’s constant buzz for the creative, laid-back energy of Brooklyn. Begin your morning in Williamsburg with a perfectly brewed coffee at a local café. Take your time wandering vintage shops, bookstores, and quirky boutiques — this neighbourhood thrives on individuality, and it’s easy to get swept up in its artsy charm. We always stack up on as many books as our baggage allows!
For the afternoon, you’ve got options:
- Head to the Brooklyn Museum, one of the largest and most diverse art collections in the country.
- Or, if you prefer the outdoors, explore Prospect Park, designed by the same masterminds behind Central Park, but with a more local, relaxed feel.
Later, make your way toward DUMBO (Down Under the Manhattan Bridge Overpass). The cobblestone streets and red-brick warehouses frame some of the most iconic views of the Manhattan skyline. Don’t forget the classic shot of the Manhattan Bridge perfectly aligned with the Empire State Building in the distance — it’s Instagram gold (again).
When hunger hits, it’s time for the food Brooklyn is most proud of: a proper New York–style pizza slice. Crispy, foldable, cheesy perfection — and yes, Brooklyn does it best. Be prepared it’s very much different than the Italian version, but it’s a must try, even if you’re into napolitana!
End your day on a dreamy note at the Brooklyn Heights Promenade. As the sun sets and the city lights flicker on, you’ll get another sweeping skyline view — this one calmer, more reflective, and the perfect counterbalance to Manhattan’s rush.
Day 5 – Uptown & A Grand Finale
Spend your final day in Harlem, a neighbourhood that has shaped much of New York’s cultural heartbeat. Stroll along 125th Street, where music drifts out of storefronts and murals tell stories of community and history. If you can, step inside a church for a live gospel choir performance – the energy, rhythm, and spirit will move you in ways no guidebook can capture. It’s one of those unforgettable experiences that stays with you long after you’ve left. It’ also quite a cultural shock if you’re not American :).
In the afternoon, head downtown to Grand Central Terminal. More than just a transit hub, it’s a temple of New York life. Pause under the celestial ceiling in the Main Concourse, watch the constant choreography of commuters rushing past, and feel the pulse of the city in motion. Take a moment to linger — this is New York at its most iconic. Try to spot the original uncleaned tile on the ceiling that has never been cleaned (on the photo).
If your lucky, there are frequently pop-up art fairs in the halls of the terminal – we bought our favourite art painting there.
For your grand finale, treat yourself to dinner at a rooftop restaurant. As the sun dips and the skyline begins to glow, raise a glass to the week you’ve just had. Watching the city light up one last time is the perfect way to say goodbye – not a farewell, but a “see you soon.”
✨ Final Thought
New York is a city that refuses to be pinned down. It roars with traffic and blazes with neon, yet in the middle of all that noise you’ll stumble upon a quiet bench in Central Park, a street musician playing just for you, or a sunset that makes the skyline glow like magic. That’s the paradox — overwhelming and intimate, all at once.
No matter how many times you come, the city is never the same twice. Neighbourhoods shift, new flavours appear, and the rhythm of life beats differently with every visit. You don’t really “do” New York – you experience it, layer by layer, moment by moment.
So whether you’re here for five days or five weeks, embrace it fully: start the morning with a bagel, grab a hotdog on the go, sink your teeth into a pastrami sandwich, and let the city surprise you in ways you didn’t expect. That’s the magic of New York – it always gives you more than you came for.
🛎️ Tips & Bookings
🎟️ Tickets & Attractions
- Broadway shows: Buy in advance if you want a specific show (The Lion King, Hamilton). For discounted same-day tickets, head to the TKTS booth in Times Square.
- Empire State Building: Sunset is magical but windy — book timed tickets online to skip the queues.
- Statue of Liberty & Ellis Island: Ferries leave from Battery Park. Book the first morning slot if you want fewer crowds.
- Museums: The Met has a “pay what you wish” policy for locals, but tourists need standard tickets — still worth every cent.
🏨 Hotels
- Budget: Pod Hotels (compact, modern rooms in central locations).
- Mid-range: CitizenM Times Square — small rooms, great design, unbeatable location.
- Splurge: The Mark on the Upper East Side (yes, Gossip Girl vibes) or The William Vale in Brooklyn for skyline views.
🚇 Transport
- Get a MetroCard (or use OMNY contactless with your card/phone) for subways and buses. Cheaper and faster than taxis.
- Comfortable shoes are a must — you’ll walk a lot.
🍴 Food & Drinks
- Katz’s Deli: It’s cash or card at the entrance counter — don’t lose your little ticket, you need it to leave.
- Bagels: Try Russ & Daughters for a true New York experience (lox & cream cheese heaven).
- Pizza: Joe’s Pizza in Greenwich Village is a classic; in Brooklyn, try Juliana’s or Grimaldi’s by the bridge.
- Coffee: Besides Starbucks, look for Bluestone Lane or Birch Coffee for great specialty brews.
✈️ Flights
- New York has three main airports: JFK, LaGuardia, and Newark. JFK handles most international flights, Newark can sometimes be cheaper (especially for downtown stays), and LaGuardia is closest if you’re flying domestic.
- Getting into Manhattan: the AirTrain + subway combo is the cheapest, while a yellow cab or rideshare is the easiest (but pricier). Always compare all three airports before booking — prices, travel time, and convenience can be very different depending on where you’re staying.
- You can book your flight HERE or HERE.
💡 Smart Tips
- Book as much as you can online – often it’s cheaper and you skip the lines.
- New York days are long and packed, so carry a foldable water bottle and a power bank for your phone.
- If you want to see multiple attractions, consider the New York CityPASS — it includes the Empire State Building, The Met, and more at a reduced rate.
🔗 Quick Links
Here are some helpful links to make planning your New York trip easier:
- 🎟️ Broadway Tickets – book in advance or check TKTS for same-day discounts
- 🗽 Statue of Liberty & Ellis Island Ferry Tickets
- 🌇 Empire State Building Tickets – best views at sunset
- 🖼️ The Met Tickets – world-class art and history
- 🏨 Hotels in New York – from budget pods to skyline luxury
- 🚇 MetroCard & OMNY Info – how to ride the subway
- 🎫 New York CityPASS – save on multiple attractions
For more travel inspirations check out my other posts or check my Pinterest account!
You can also visit my Etsy shop for New York inspired T-Shirt!
