5-day new york city itinerary: the perfect nyc trip for first-time visitors

We just arrived back from a bit of a whirlwind trip to NYC, and it was wonderful. Sure, we had our moments of exhaustion coming on the tail end of a big move + graduation, {we covered walking over 35 miles in just a few days}, but it was a great adventure for the whole family. We happened to have some leftover tickets from a trip we weren’t able to take earlier in the year, so we decided to reroute to NYC for a family trip, to celebrate summer + graduation. With three teens who’ve never been {This would be Jamin’s third trip, and I’ve lost count, but it had been a minute}, this was actually a great run. In case anyone was curious, I’m sharing it all here with links and maps to boot. 5-Day New York City Itinerary: The Perfect NYC Trip for First-Time Visitors

Disclaimer: Of course, “the best itinerary” is debatable. Yay SEO. But it was so fun, we thought it might be good to share in case anyone else was debating all things trips. This includes our main stops- sure, it was super touristy, so don’t come at me if you’re a purist, but I think that’s why you go. Use our times loosely; these were the original schedule, but then we shifted them accordingly.

Food: We grabbed food on the go and didn’t plan out many of our meals, but I will recommend a few stops here. Many were at the mercy of the streets, and most of the time they didn’t disappoint. If you have enough untouched leftovers, I recommend properly boxing them up and handing them to someone in need, afterward. Spending so much on food felt a little better when the excess went to someone else. 

 

Wanderlust: We also let some stops guide us along the way. If we weren’t sure, we asked a local. Most of them were super friendly and helpful- Especially the doormen. They literally know all. We also recommend stopping wherever you see fit in various stores, etc. 

Location: This itinerary includes travel days + is based on our location. With a family of five {three young adults}, we needed four queen-sized beds and two rooms. We didn’t stay anywhere fancy, so it was a great way to save, but it was perfectly sufficient, safe, and clean. My only complaint would be the elevators being a little slow, but that’s a common issue. This was a great space from which we could base our routes. It was near a local Walgreens where we could grab bottled water and snacks/breakfast stuff when needed. We were only there to sleep. Winning. 

Transportation throughout: Included a mix of mostly subway {challenging at first to navigate but an experience all its own- we did get lost at one point because they closed down a train}, walking, + the occasional Uber / Lyft scenario if we were absolutely exhausted. In short, pack your walking shoes. 

Day 1:
• Flight: {We took a mid-morning flight direct from BNA to LGA via Southwest}
• 5th Avenue: and by the time we arrived, we were able to check in and walk around.
We went to 5th Avenue + Madison for a little touristy perusing {See FAO Schwartz, The Lego Store, etc.} and grabbed some street pizza. Emerson has a friend from NYC who made a lot of these recs – she told us that anything over 5 dollars won’t be good. She was right.

• Broadway: Then back to change for The Great Gatsby on Broadway. This one was Emerson’s favorite book in high school (mine too), so it was a must-see. Daisy was phenomenal, {Fun fact: Daisy + Gatsby are married IRL}, and the sets + costume design + color were so well done. {See Google Maps, here.} 

• Times Square: After that, it was a walk to Times Square {The best time to see it is at night} where we were totally overstimulated, and purchased boxes of Krispy Kreme from their gigantic store to take back to the hotel. Because ‘MURICA. 

Day 2: • 10:00 – Shopping in SOHO: We were glad to take our first morning a little slower since we were out until midnight the first night. The best shopping streets are Broadway + Prince St. Again, let the locals direct you, too. {Here’s a broad map of what we did}. Emerson snagged a pair of cute Steve Maddens, and I felt like I’d traveled back in time when I spied a pair of these on prominent display. 

{PSSST… if you’re a safe bathroom person like me, make a stop at Bloomingdale’s.} 
• If they’re open, hit Mimi’s Frozen Yogurt. 

• 12:30 – Little Italy + China Town – Walk through Little Italy on your way to Chinatown. We stopped for lunch at a side area in Little Italy, but this one was a miss, so I won’t share it. Most of the time, they won’t disappoint, but this one was our least favorite. I think half our problem was that it was a hot morning, and the food was rich. We tried to be really careful about splitting meals and eating in smaller quantities for that reason. We were sitting on the sidewalk when we spied Ilona Maher – so that was a plus. We didn’t want to bother her, since she was already being bombarded by someone else, but it was pretty cool to see her IRL. 

• 2:30 – Washington Square Park: On your way to the next destination, check out Washington Square Park, for classic NYC atmosphere and great street performers. 

• 3:30 – Carrie Bradshaw’s House: It’s one of my faves. This one was fun for the sake of nostalgia. Located at 66 Perry Street. There will be a small crowd, and the owner has put up a gate, which I get… I can’t imagine what it’s like to live there. But also, she had like twenty years to know what she was getting into, so it is what it is. We also walked the West Village, which is easily one of NYC’s prettiest neighborhoods. 

• Toby’s Estate Coffee: Magnolia’s was overrun, so we hit the sweetest people with the best coffee, {and another safe bathroom.}

Total side note: At this point, we had our second celebrity sighting and didn’t realize it until he’d passed us. Emerson has a gift for faces, where she can name the actor from any movie. As it turns out, this translates brilliantly in real life. We googled his tattoo + dog to confirm. He actually called someone out about not cleaning up after their dog, but did it in such a kind way that we were impressed. 

• Little Island: After this, we made a visit to Little Island with small walking trails + a bay area to look out at the city + water. 

• 6:00 – The High Line – Walk North toward Hudson Yards + see more of the sights here.

• Chelsea Market here is a must-see with great little shops – If you’ve been to Franklin before {where we live}, this is The Factory on steroids. I still can’t believe I didn’t walk away with this – I was afraid it would break – and may have to order it.

• 7:00 – The Edge – Move onward to the Edge at sunset. See more of that here. 

• Stop by Grand Central Station on your way back. Don’t miss the whispering gallery. 

Day 3: 
• 9:30 – The 911 Memorial: You could honestly stay here all day. It was really good for our kids to see it firsthand. Seeing how it impacted everything up close and personal is definitely one of the best stops you can make.

• Afterward, we went to the nearby shopping center and grabbed some lunch at the local food court, which had a variety of options. 

• 1:00 – One World Trade Center Observatory: A great way to see the city in all directions. We recommend you stay for the little presentation they give here, where they educate visitors on the 5 boroughs of NY, and all the things you can see from each direction. 

• 2:00 – The Bull + Wallstreet – It was actually really packed this day, so we didn’t get really close for a photo op, but the kids were glad to see it. 

• Trinity Church: Here, we took a side quest to see this beautiful church and cemetery. Many of NYC’s founding fathers are buried here, including Hamilton. 

• 3:30 – The Staten Island Ferry: We opted to take the free ferry to get a few shots of our lady. This was free and took about 30 minutes each way. I’ve been to the top of the Statue of Liberty before, but these days with security and lines, it can easily eat up a good portion of your day, and we had a lot to see. So we opted for this instead. Sit on the right side as you go in. You have to get off and get back on, on the other side. Lots of crowds, but it’s a great, cooling activity. 

• 5:00 –  Dumbo + Pebble Beach + Brooklyn Bridge – We were able to see some great views here – One of the kids commented this was their favorite area. We had plans to walk the Brooklyn Bridge after that, but by then, I was pooped on by a bird, it was in my hair, and we were absolute TOAST. {Shout out to the super kind fellow mom who handed me a wet wipe, as it was in my hair. I’ve now been pooped on like 5 times in my life, it’s actually wild – so I’m still waiting on my good luck?} It was good to see it and check out a few shops instead.

• Thea Grant: We stumbled upon this store, and highly recommend checking it out if you’re in the area for one-of-a-kind finds and jewelry.

• 6:00 – Dinner at Rosa Mexicano: Recommended years ago by a friend, this was our second visit. So. GOOD.

• Empire State Building: On your walk to the Empire State Building, check out the Flat Iron Building. {For around 17 mil, you can totes live there.} + Penn Station. 

Day 4: 
9:30 – St. Patrick’s Cathedral: Check out this historical church – the architecture alone is a marvel. Hello, stained glass. 

12:00 – Rockefeller Center + Top of the Rock: No, we couldn’t get enough of those skyline views. We enjoyed the historical take on this one, too. 

3:00 – Radio City Music. Hall – Our plans after this were to return to Radio City Music Hall for a tour, but they were closed for the week due to a special event. Bummer, but we hit the venue below.

• Bike Central Park – Here, we rented some bikes and did the Central Park thing.
We’ve done this before, but it was a different vibe with three teens. The boys proclaimed it their favorite part. Have you ever been to Disney and, by the end of the trip, wanted to scream because you’re so over all the people? This is like that, except Disney snorted Cocaine at the end of a bender, and you might actually die. It felt a bit like herding small kittens to one location while dodging small missiles, and the small missiles were other insane riders going around 50 mph.

Emerson had a bad accident at a friend’s house a few years ago, which required staples in her head, along with a concussion, so I wasn’t messing around with helmets, either. But YOLO, it does make for a fun memory even if we have lice now. KIDDING. The kids can laugh about the time mom melted in the middle of Central Park over a granola bar because I hadn’t really eaten that day, and WHERE ARE THE BATHROOMS?! And then they closed off part of the park, so we had to navigate a back trail instead of driving head-on into oncoming traffic… Yes, NYC comes with its white-knuckle moments, too. Let’s just say Tiffany’s is more my vibe, but the kids loved it so it was a win.

• Shopping – Be sure to hit the classics like Tiffany and Coach – There were so many things to take in. It was also great to decompress after our life and death event. 

• Street Food – Yep. The kids were begging. We were told that if we tried a hot dog, it had to be Nathan’s. So that’s what we did. 

Day 5: 
• Our flight back was that day, so we packed our bags beforehand, and in between the two stops, checked our baggage with the front lobby so we could still explore. 

• 9:30 -The New York Public Library: Lots of things to see here, as well as the beautiful architecture. 

• They also had the original Winnie the Pooh on display, which was pretty cool, amongst other things. 

• The MOMA: We topped off our trip with the Museum of Modern Art, before heading to the airport. One of my personal faves, and the fam humored me. Even if in the furniture section, Jamin did say, “This one is titled: ‘Rejected Ikea Pieces” The fifth floor was by far the best, where you can see Seurat, Monet, Hopper, Van Gogh’s Starry Night, Picasso, Matisse, and more. 

And that wraps up our trip! It was a whirlwind, and we’re tired, but it was a blast, too. If you use any of this, please let me know. I’d love to hear your experience. We hope this is helpful. Have an inspired day!