New York is a full-volume city. Energy, lights, sirens, steam vents, accents, attitude, people—like someone turned the world’s energy up two notches and snapped the knob off.
I’ve been to New York six times. Each trip taught me something the last one missed. The first time, I tried to see everything and left exhausted and some cranky. The second time, I followed someone else’s perfect itinerary and felt like I was checking boxes for someone else’s trip. By the sixth time, I’d figured it out.
Three days in New York isn’t enough to know the city—but it’s enough to feel it. And if you do it right, you’ll leave understanding why eight million people choose chaos over comfort every single day. Coming from Newfoundland where you can drive for an hour and see maybe three other cars, that’s saying something.
This isn’t a “best of NYC” list. It’s not optimized for Instagram or designed to impress anyone. This is exactly how I spent three days in New York on my latest visit. So here’s my NYC 3-day plan if you want to stay in the Midtown / Times Square / Theater District / Central Park orbit and walk everywhere like you actually live here (for 72 hours).
No tourist traps. No regrets. Just the real thing.
If you want to walk everywhere without overthinking it, stay between Times Square and Central Park.
Think:
42nd–59th Streets
Between 5th Avenue and 8th Avenue
This stretch puts you exactly where you want to be:
A straight, easy walk south into the Theater District and Times Square
A straight, easy walk north into Central Park
Quick access to 5th Avenue, Rockefeller Center, MoMA, Carnegie Hall, and Midtown icons
Busy enough to feel safe at night, but not so chaotic that you can’t breathe
This is the part of Manhattan where distances actually make sense on foot. You’re never more than 10–30 minutes from anything you’ll want to do on this trip.
If your hotel is somewhere between Times Square and 59th Street, you’ve done it right. Everything in this itinerary flows naturally from there.
Donny Tip: On my last trip I stayed at the Residence Inn at 1717 Broadway and 54th. Super conveniently located about a 10 minute walk from Central Park and a 10 Minute walk to Time Square, and it sits right in the heart of midtown’s Theatre District. It’s a 7 minute walk straight down Broadway to a CVS pharmacy, a 4 minute down Broadway to a Duane Reid Mini Grocery, and a 2 minute walk up Broadway to a large Bodega with a cafe and a fabulous food bar. This is my second time staying at this Residence Inn and it feels even more convenient this time around!
Late April through early June, or September through October. Summer is brutal—95-degree heat radiating off concrete, subway platforms that feel like saunas, hotel prices that spike during peak season. I’m used to Newfoundland summers where 20 degrees is a scorcher, so trust me when I say NYC in July will wreck you. Winter is cold and beautiful if you can handle it, especially around the holidays when the city goes full Christmas Rockefeller Center style. But spring and fall give you the best version of the city: walkable temperatures, manageable crowds, and that perfect light that makes every street photogenic.
New York is expensive. Accept that early.
Plan loosely. Don’t let sticker shock steal the joy.
Theme: Classic New York, layered properly.
Go to Times Square early before the crowds. Take it in. Shop if you want. Grab breakfast.
You’re in a culture-dense pocket. Pick what fits your mood:
MoMA (Museum of Modern Art)
Radio City Music Hall Tour
St. Patrick’s Cathedral
There are great restaurants and cafes for all your food desires. Find one on your journey and enjoy. Take a breath and move on. You’ve got ground to cover.
This stretch is perfect for window shopping + one intentional stop.
5th Avenue (Iconic):
Madison Avenue (More refined):
Columbus Circle area:
Even if you don’t buy a thing, this walk tells you a lot about New York.
Donny Pro Tip:
Macy’s New York flagship store on 34th and 8th ave is about 8 blocks past Times Square but well worth the extra 12 minute walk to see the world’s largest department store. I went and it was pretty cool!
As the lights come on, walk west into the Theater District.
Dinner options (pre-theater friendly):
Theater Options:
If you’re not seeing a show tonight, just walk the district. It’s alive in a way few places are.
Donny Tips:
On my latest trip I went to the Great Gatsby and Moulin Rouge, and both were spectacular performances. Gatsby is weighty and serious, and a must see for fans of the movie or fans of F. Scott Fitzgerald. Moulin Rouge is a visual masterpiece with pop songs that you probably know, but it’s a little risque and definitely not for the kids!
Theme: Reset your nervous system.
Enter the park at 59th and 7th.
Don’t try to “do” Central Park. Pick a graceful route:
Sit. Watch. Let the city fade out for a bit.
Exit the park on the east side and pick one:
The Met
The Guggenheim
The Frick Collective
I did the Frick on my latest trip and it was spectacular. Set in the Frick Mansion at 70th and 5th ave. It was interesting to see all the art that Frick collected, and a marvel to think about his existence in New York in the 1920s living in such an impressive grand house on 5th ave. Tickets for the Frick are for a specific time of the day which helps with crowds.
Skip museums entirely if they don’t light you up. No guilt.
Brunchy, relaxed options near the park:
This is prime unstructured time.
This is where New York starts to feel familiar instead of impressive.
Tonight is about good food, not hype. And before or after dinner take 20 minutes to walk through Times Square to feel the energy and get the experience of the madness. It’s an impressive spectacle.
Dinner styles that work well:
Theme: Follow instinct.
Pick what pulls you in:
Grand Central Terminal
Rockefeller Center Area
Hudson River Walk (Midtown West)
This is where the trip settles.
Repeat a place you liked. Or finally try the spot you kept passing and thinking about.
Option A: Broadway Musical or a Jazz Club
End big. Let the city perform for you one last time.
Option B: One Perfect Drink
Somewhere quiet. Somewhere you can talk.
Option C: Hotel Window + City Lights
Honestly? Underrated. Sometimes the best ending is just watching New York be New York.
New York doesn’t bend for you.
But if you stay central, walk with intention, and stop trying to conquer it, the city opens up.
Three days won’t make you a New Yorker.
But it’ll show you what it feels like to move through a place that’s fully alive.
And that’s worth the trip.
Until the next adventure,
Donny Love
Adventures Unknown – The best stories are the ones you live yourself.
Donny Love is the star of the Adventures Unknown Television Series, host of The Donny Love Radio Show, and a Newfoundlander who’s rarely standing still. He’s out exploring the world one adventure at a time — and writing about it honestly, so you know what’s worth doing and what’s not.
