There are two types of people who go to New York City for the first time:

1. The people who show up with no plan and wander around.
2. The people who create a color-coded itinerary, research every neighborhood, read 37 travel blogs, and map every walking route in advance.

I am proudly the second type.

So when Bryan surprised me with a long weekend trip to New York City for my 50th birthday, I did what any normal person would do…

I spent weeks researching Manhattan like I was preparing for the Olympics of tourism.

Because when you only have Friday to Monday in New York, every minute counts.

In just one long weekend we managed to:

• Walk over the Brooklyn Bridge at sunrise
• Eat some of the best tacos and Italian food we’ve ever had
• Take in breathtaking views from Top of the Rock
• Explore Central Park by pedicab
• Visit the moving 9/11 Memorial & Museum
• Watch the New York skyline light up from the water at sunset
• Wander through Greenwich Village, Chinatown, and Little Italy
• And somehow… I even ended up getting a birthday hug from Hugh Jackman outside Radio City Music Hall.

Not a bad way to start turning 50.

If you’re planning your first trip to New York City, or just looking for ideas on how to spend a long weekend in Manhattan, here’s exactly how our trip unfolded.

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What You’ll Find in This NYC Series

✔ Detailed daily itineraries
✔ Restaurant recommendations
✔ Rooftop bars worth visiting
✔ Travel tips for first-time NYC visitors
✔ Honest thoughts on the most popular attractions
✔ And a few funny moments along the way

Because if there’s one thing I learned during our trip…

New York City somehow manages to be even better than you imagine.

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NYC Trip Stats

• 4 days in New York City
• 100,000+ steps walked
• 45 miles explored
• 1 Broadway show
• 1 Hugh Jackman birthday hug
• Countless compliments about Bryan’s biceps

Our 4-Day NYC Itinerary

Day 1 – Midtown Manhattan, Top of the Rock & Hugh Jackman

Bryant Park • Grand Central • Rockefeller Center • Radio City Music Hall
➡ Read Day 1

Day 2 – Brooklyn Bridge, DUMBO & Central Park

Pebble Beach • Chinatown • Little Italy • Pedicab tour • Harbor Lights cruise
➡ Read Day 2

Day 3 – 9/11 Memorial, Greenwich Village & Broadway

Wall Street • Washington Square Park • High Line • Book of Mormon
➡ Read Day 3

Day 4 – One Last Morning in New York

Friends Experience • Empire State Building • Guggenheim • Plaza Hotel
➡ Read Day 4

🍽️ Looking for restaurant recommendations?
I put together a list of the places we loved in New York — plus a few that are already on our list for next time.
👉 [Read the NYC Restaurant Guide here]