My New York City 2025 Travel Diary: Highlights, Mistakes & Must-Do’s

In May, we spent about 6 days in New York City so I wanted to put together some travel tips / notes from my trip as a Trip Overview before creating more specific posts, like a NYC itinerary, how to get into a Peloton NYC live recording class, etc. I’m hoping to have those more specific posts up soon, but for now, here’s most of the key information and general travel tips from our trip.

Trip Overview: Key Facts from My Trip

• Dates: May 17th – 19th & May 22nd – 26th
• Total Days: About 6 days
• Who?: Me + my husband (Dom)
• Reason: I had a work trip in Jersey City, so we went to NYC for a few days before and a few days after (in Manhattan both times) since we’d never been and it’s right across the river
• Getting there: Drove to Chicago, Flew to JFK, took the subway to Manhattan; took the PATH to and from Jersey City
• Getting around: We exclusively took the Subway – no taxis! My friend Chuck that I see at Starbucks almost every day was disappointed – he wanted to know what the minimum ride fare is in a taxi these days; he said he used to visit NYC quite a bit when he lived in Philadelphia.
• Lodging: Courtyard New York Manhattan / Central Park

Top 4 Best Experiences in New York City You Shouldn’t Miss

Walking Through Central Park

Everyone says it’s hard to imagine, and they’re right. I couldn’t believe how expansive it is, and how it really felt like I was in a forest – even with the visible tops of the skyscrapers. It quickly made me realize just how small Chicago is compared to NYC. If you only have time to do one walk in Central Park, I would try to walk to the Bethesda Terrace and Fountain, the Bow Bridge, Belvedere Castle, and then on to South Gate House / south side of the Jacqueline Kennedy Onassis Reservoir. Walking to those four things gives you a pretty good overview of the park – but you could realistically spend weeks exploring all of the different pieces of it.

Experiencing a live Peloton NYC recording

I can’t lie, I cried a little in my first class when Ally Love walked in and started talking to us. After years of seeing the studio and instructors on a screen, it felt surreal to be in the room in person.

Going to the 9/11 Memorial and Museum

I’ve watched the videos so many times – each anniversary, in all of the documentaries – and I’d even seen One World Trade Center from a distance on a prior trip to Jersey City, but there was something so different about standing in the memorial area, seeing the two memorials, doing the audio tour, and really trying to wrap my head around it. For me, the hardest part of the tour was after I’d noticed there were a few white roses in names around the memorials, and shortly after, our tour guide told us that every morning, someone goes out and puts the white roses in the names of each person whose birthday it is. I think especially because we were only a few days away from my birthday, this really got to me and made me cry a bit. Anyway, going to the memorial and museum is something that you should prioritize if you’re making a trip to NYC; I was probably most glad that we did this of everything we did on our trip.

Watching The Book of Mormon (or any other music-focused show) on Broadway

I didn’t know much about this one prior to seeing it except that some of the humor is edgy / controversial, that one of the guys wants to go to Orlando, and that Josh Gad was in the original. The humor was a bit much for me at times, but the singing was just absolutely phenomenal. We also saw The Lion King on Broadway and the costuming there was so next level, but the singing in The Book of Mormon really stood out to me. I think seeing these two taught me that I’m more of a music-Broadway person than a visual-Broadway person? So if you have any tips on other Broadway shows I should prioritize, let me know!

Biggest Surprises About Visiting New York City

It’s truly the city that never sleeps

We didn’t get to Manhattan until midnight because we landed late due to a flight delay + it takes about an hour to get from JFK to Manhattan via the subway, and couldn’t believe how many places were still open. I grabbed a slice of $1.50 pizza (which was still good, but probably the worst of the five or so New York style pizza places we tried on this trip), we walked past open Gelato places, walked through a 24-hour grocery store – it was amazing. It still felt really busy – not like only a few people were out and about.

I was absolutely obsessed with the city

I was immediately like… yeah, I think I could live here – at least for a little while. Of course, financially it would be catastrophic, but it just was such a cool experience. Seeing all the runners and bikers in Central Park every morning and all the regulars at the tiny coffee shops I tried and in the Peloton NYC studio – I completely understood how obsessed Nora was with NYC in Book Lovers (by Emily Henry) and switched to re-listen to the audiobook of Book Lovers mid-Central Park walk because I finally understood where she was coming from. (I want to re-read the physical copy and annotate all of the references to NYC that I really get now).

Unfortunately… the trash… everywhere

I’d heard people say that New York City has way more trash on the streets and sidewalks than Chicago because Chicago has tons of alleys for trash and NYC doesn’t, but still couldn’t believe what a difference this makes until I saw it.

Wall Street was just as touristy as Times Square

• This was one that Dom pointed out and is incredibly true; I talk more about this below; I’m glad I saw it once, but I likely won’t go out of my way to see it again.

We could use Apple Pay for the subway

I hate to be that person comparing Chicago and NYC again, but Chicago needs to get on this ASAP. The system also caps how much you’re charged in a week, which is nice – so you don’t have to do the math and figure out if it’s cheaper to get a week-long pass.

Pier 55 – Little Island

I’d never heard about Little Island in NYC before our trip, but our walking tour guide on The High Line – yes, the High Line that is featured in the Taylor Swift song Cardigan – pointed this park out to us (before we left the tour) – it looked really cool so we went over to it and I’m really glad we did. It’s essentially a fun, floating, multi-leveled park. Next to it is (as you might expect) Pier 54, which is coincidentally where the RMS Carpathia docked – it’s the ship that picked up the Titanic survivors, so there were some markers / info about that. Apparently, the Titanic was scheduled to dock at Pier 59.

I LOVED seeing Van Gogh Starry Night painting at the Museum of Modern Art (MOMA)

I was caught off guard by just how cool I felt like this was; buying tickets for MOMA was worth it just to see Starry Night alone. I would honestly go back to MOMA just to see it again. I think because it’s like in the top 5 most recognizable paintings of all time, it was shocking to see the real thing in person.

Broadway is a huge group of qualifying theaters, mostly off of Broadway Street

Maybe I’m dumb, but I thought there was only like 1 theater and all the plays took turns. I only realized there were more than one Broadway theater when we starting looking at tickets to shows while we were planning our trip. I then realized there were more than “a couple” theaters while we were actually there and I started seeing them all, and while writing this post I actually Googled it and found out there are 41 theaters “On Broadway”.

Top Things I’ll Prioritize on My Next Trip to Manhattan:

Go back to Broad Nosh Bagels and Russ & Daughters Bagels

• Both famous bagels shops were phenomenal and I can’t pick a favorite between them, so I’m putting them both here. Broad Nosh was best for the sweeter options (we got an incredible toasted cinnamon raisin bagel with cookie butter cream cheese) and more “basic” bagel sandwiches (we split an everything bagel sandwich with avocado and egg). Russ & Daughter is more traditional – Dom had a toasted everything bagel with egg salad on it, and I had a toasted everything bagel with classic cream cheese. We also tried a slice of babka in honor of the Seinfeld episode where the babka is the main plot line of the episode, and it was really good.
• Both Broad Nosh and Russ & Daughters have multiple locations. The Broad Nosh shop near Central Park is their famous shop and it seemingly always has absolutely insane lines; we walked by after our morning run / walk and decided to skip it, so we were glad that the one on 42nd St and 9th Ave had a much shorter line.
• We went to the Russ & Daughters in Hudson Yards – it’s only a block away from Peloton NYC, which is great if you have a quick break between two classes like we did and want a snack.

Do more in-studio Peloton NYC classes

I think I kind of expected this trip to get live lasses out of my system, but it didn’t – I 100% plan to try and get into a few classes on every future trip to NYC. The best Peloton cycle instructors in person (IMO) were Alex Toussaint, Ally Love, and Hannah Corbin. I’ve been doing all three of their rides pretty much exclusively since I got back home. I was also incredibly inspired by the live Yoga class I did with Nico Sarani – I’ve done 10 mins of yoga every day since my birthday partially because her yoga was so beautiful that it made me want to put more effort into my own practice.

Go back to McNally Jackson Books

McNally Jackson has 5 locations in the city (see the fun sketch of all five storefronts below from their website) and we only went to the Seaport location, so I’d like to make it back to their Seaport store because it was gorgeous, and hopefully to one of the other locations next time we’re there.

What I Might Do Again on a Future NYC Trip:

Go to Another Yankees Game

We had a ton of fun at the game we went to – it was the Yankees vs Mets, so the energy was amazing. It’s really easy to get to the stadium (find a B, D, or 4 subway station and follow all the people wearing Yankees merch to the 161 St-Yankee Stadium stop). It’s not something I need to do on every trip but I would probably check to see if they’re playing at home when we’re planning a future trip.

Go back to Rizzoli Bookstore

I was glad we stopped in because it was a really nice bookstore with a great selection, but I wouldn’t go out of my way to go by again. If you’re a reader looking for a bookstore to stop by in Manhattan near the Flatiron building / where 5th Ave and Broadway intersect, I would add it to your stops.

Things I Missed and Want to Do Next Time in NYC:

Spend time in the other Boroughs

We didn’t really make it out of Manhattan (except briefly to the Bronx for the Mets @ Yankees game) and I know there are a few places that I’d heard good things about in Brooklyn, especially. So that’s on my list for next time.

Walk or run across the Brooklyn Bridge

We didn’t make it there and I’ve heard it’s best to go really early in the morning to beat the crowds. We had a lot of fun in Central Park each morning so I’m not mad we didn’t make it there, but it would have been nice to do both.

Go to the New York City Public Library

We were able to walk around the outside a bit but it closed early for the Memorial Day weekend, and it seemed massive.

Try food in Little Italy

We did make it to Chinatown (make sure you bring cash, or there are a lot of Chase + other popular banks’ ATMs around!) which was really good, but then we just walked through Little Italy on our way back to our hotel and weren’t hungry enough to stop in anywhere.

Go to the Statue of Liberty

We actually did have tickets to go to it, but it was a super rainy day and we decided to skip it – not the best place to stand in line for a boat and take a mostly uncovered boat to in the rain. We did get to see it from Liberty State Park in Jersey City, though.

See a performance at Carnegie Hall

I’m a music person, like I mentioned when I talked about The Book of Mormon, so I’d love to see a performance by the New York Symphony or an incredible pianist in Carnegie Hall someday. It didn’t work out on this trip, but hopefully it will on a future one!

Rent road bikes and bike some of the popular routes – including around Central Park

If I’d had room to bring my bike shoes and clothes, I might have more seriously considered this, but my carry-on was stuffed enough without bike clothes. Also, the only way to use the clip-in shoes is to bring the pedals as well. So, it would have been a big commitment – maybe next trip, or sometime when we can road trip out there and bring our own bikes with us.

Go to My Pie Pizzeria Romana

On one of our days in NYC, Dom and I split up – I went to some Peloton NYC Studio classes while he went to the Met, and afterwards he stopped at a pizza place and never stopped talking about it for the rest of the trip. We didn’t make it back over there for me to try it, so we have to go back on our next trip.

Go to the Met

This was another thing that Dom did while I was at Peloton NYC classes, so I’d like to go at some point – but I’m kind of a one art museum-per-trip kind of person, so I’m kind of glad I didn’t go to both the Met and MOMA on this trip.

Go to a live TV show taping

I’d especially love to get tickets to see a taping of Jimmy Fallon or SNL.

What I’m Glad I Did in NYC, But Won’t Repeat

Go to the Barnes & Noble flagship store

(105 5th Ave) – it’s 4 stories tall and was really fun to see because they just have so many books, but it’s not something I need to see again. There are way too many other / indie bookstores in the city – especially if we make it out of Manhattan next visit and go to some in the other boroughs.

Seeing The Lion King on Broadway

The Lion King on Broadway was really cool and I’m so glad we saw it, but there are too many other Broadway shows that I’d like to see to go back to it. Same with The Book of Mormon, most likely – but I’d probably see that one again before I went back to The Lion King just because the singing was so good in The Book of Mormon.

Best Restaurants & Dishes We Ate in Manhattan

Dinner at Blue Willow near Central Park

• After a trip to Yellowstone National Park, we learned our lesson – if a place is good enough that you even think about eating there a second time instead of trying somewhere new… go back to the place. The new place will almost definitely be disappointing by comparison. The vegan cauliflower dish that Blue Willow serves is out of this world – by far the best cauliflower I’ve ever had. It’s flavored absolutely perfectly. Dom ordered the Changsha spicy chicken on our second visit and liked it, but he would have preferred to have more chicken – it was a lot of the peppers on the plate.

Favorite Pizza Places in NYC: My Pie Pizzeria Romana & NY Pizza Suprema

• My Pie Pizzeria Romana. Dom maintains this is the best pizza he had in NYC, but this seems to be a personal favorite – most people seem to prefer Joe’s Pizza near the World Trade Center.
• NY Pizza Suprema. If you’re by Peloton NYC or Madison Square Garden, stop by NY Pizza Suprema for a slice of the mushroom pizza. It was my personal favorite pizza of the trip – like I mentioned with Blue Willow, it was good enough that I went back a second time. They also had a lot of vegan pizza options.

Favorite Bagels in NYC: Broad Nosh and Russ & Daughters

• I know I already mentioned this, but these are two of the bagel shops that you’ll likely hear about if you look up NYC spots to try on TikTok. Read my description up above!

Best Dessert near Times Square and Broadway: Angelina Bakery

• This is a really cute bakery with tons of display cases in the windows, which is what caught our eye – it’s on Broadway near Times Square. We went twice – the mini cannolis were really cute and delicious, and I loved the Nutella tart that I had. The pizza slices were also huge and delicious; I would skip the pasta though – it was clear after we ordered it that it 1) was something they don’t make often and 2) isn’t worth the price.

Other NYC Restaurants We Liked, But Probably Won’t To

• Joe’s Pizza – this is a pizza place near the 9/11 Memorial and Museum that is very famous – there were dozens of photos on the walls with famous people. It was good but not the best pizza we had in the city; we were still glad we went though since it’s so popular
• La Pecora Bianca – this was a really cute Italian restaurant with lots of fun cocktails and delicious pastas. I had the cacao e Pepe and it was delicious; Dom had the salmon and it was good, but not anything too special.
• Liberty Bagels is one of the other famous bagel shops in NYC – it was good and fun, especially because they have a fun variety of colorfully dyed bagels, but the other two shops were better.
• Eating at Uncle Lou’s in Chinatown. Uncle Lou’s is incredibly popular; it was delicious and I’m glad we went, but there are too many other places in Chinatown alone to try so I probably wouldn’t go back. I had their veggie spring rolls and General Tso’s tofu and it was really good.
• The Bus Stop Cafe – we originally planned to just walk by and get a photo since The Bus Stop is likely what Taylor Swift refers to in her Folklore song The One; in my head, Taylor Swift walked by The Bus Stop and thought she saw the person she’s singing about sitting and eating in their outdoor seating. It’s a short walk from the south end of The High Line and when we got there, it looked good and we were hungry, so we grabbed brunch. It was good but not something I’d repeat just because, like I mentioned with Uncle Lou’s, there are just too many other places to eat and not enough time.
• Venchi gelato – it was good, but not something I’d go out of my way to have again since there are so many dessert places in the city and we liked the pastries / cannolis we had at Angelina Bakery more than the gelato at Venchi.
• The Halal Guys. I wasn’t hungry so I didn’t try it, but since it’s famous, I was glad Dom tried it – he was hungry before we went to MOMA. He said it was just okay though and wouldn’t get it again.

Best Coffee Shops in Manhattan

Zibetto’s Espresso Bar

This is near Central Park and I stopped here twice on our trip for a vanilla latte. It’s a tiny, hallway of a shop – half of it is the walking space, and half of it is the counter / barista area with the fancy espresso machine and all kinds of delicious looking French pastries. It was really fun to see the locals come through – we even saw one flip the iPad around and check herself out as the employees made her regular order. There’s a tiny counter where you can drink your espresso if you order it for here, but most people ordered to go.

Ground Central Coffee

I really liked this shop – the coffee was good and it had a dark, cozy, library vibe. It’s close to Broadway and pretty close to Times Square.

Where to Stay Near Central Park, Broadway and Times Square: Courtyard NY Manhattan / Central Park

As a quick review for the Courtyard New York Manhattan / Central Park: it’s reasonably priced; on the northern edge of the Theaer District so it’s an easy, few blocks walk from Central Park, Broadway, and Times Square; was really close to several subway stations and was nice enough. There are an unlimited number of fancier, more expensive hotels in Manhattan – but since we knew we were going to be spending every waking moment out of the hotel and exploring the city, we didn’t want to splurge on losing for this trip

I think my only small complaints were:

• The shower curtain liner in our room needed replaced and we had to ask twice; (this is strangely common in hotels I feel like, though?)
• There are only a few small elevators and a lot of rooms in the hotel – sometimes it would take a while in the morning for one to stop on our floor that had room for us to get in, or there’d be a bit of a line for one to get up to our room.
• There was very loud construction outside our room during the day – can’t really hold that against the hotel because it’s not the hotel’s fault, but this wouldn’t have been ideal if we were planning to work from the room or go back to the room for a kid’s nap (or yours! no judgment – I love a good nap) during the day.

NYC Tourist Spots to Avoid if You Hate Crowds

The Battery

We went to The Battery park and it was completely unimpressive – there were a lot of people selling fake Louis Vuittons, lots of trash, lots of construction, tons of people, and not really any good views of The Statue of Liberty even though it’s really close. (Apparently, the best way to see The Statue of Liberty without actually going to it is to take the Staten Island Ferry – a lot of people told me this throughout our trip.)

Skip The High Line in the afternoon – go in the morning

If you’re a Taylor Swift fan, this might sound familiar – it’s in her Folklore song Cardigan – and it was really cool, but it’s way better first thing in the morning because the path on The High Line is really narrow. If you go in the afternoon, it’s incredibly congested – we saw a young boy accidentally step off the edge of the path into a garden area and roll his ankle a bit; there were just so many people there. The High Line itself is really cool, though – just try to walk it between 8a and 9a before crowds arrive, especially on the weekends. There’s a giant pigeon statue on the north end (in Hudson Yards / near Peloton NYC) which was fun to see.

Wall Street

Like I mentioned above, we had no idea that Wall Street would be so touristy – it was just as touristy as Times Square, but without any fake Mickey Mouse costumes. The line to get pictures in front of the Charging Bull was insane; I was glad I was able to get a pretty good picture of Dom on one side of it, though. It was cool to see The Fearless Girl, the front of Wall Street, and The Federal Reserve – but not something we would go to again mostly because of how touristy it was. Also, note that the Stock Exchange building isn’t open to the public anymore, so you can’t walk inside.

Mistakes I Made on My New York City Trip

Every trip has its hiccups, so here were some of ours. They were all just live and learn moments and nothing catastrophic – but I wanted to mention them to give you a heads up in case you’re planning a trip to NYC.

Not preparing enough for how to get from JFK to Manhattan via the AirTrain & subway

This wasn’t *that* bad for us, but we did get a little confused on exactly what we were doing / what signs to follow and I wished I’d done the research ahead of time and known the plan. I’m working on a post about this, but essentially, we needed to follow the signs to the Jamaica AirTrain station, pay the $8 AirTrain fee, follow the signs to the subway station to the city, pay the $2.90 fee, and then find the train that will take you to wherever you’re staying. For us, since we were staying at the Courtyard by Marriott New York Manhattan / Central Park near Broadway, we needed to take the E train toward the World Trade Center and get off at 7 Ave.

Doing a walking tour of The High Line

The free walking tours of The High Line aren’t very common – only a couple week and seasonal – but they’re free and we love walking tours, so we decided to pencil it into our schedule. After about 20 minutes, we ended up letting the group get ahead of us – it just wasn’t quite as interesting or informative as we were hoping for, and to be honest, a few of the other people on the tour were a little grating, so we weren’t having a great time. In hindsight, we should have brought our headphones and looked for an app / audio tour – maybe next time.

and… walking the rest of The High Line in the afternoon instead of the morning

After we ditched the walking tour, we grabbed breakfast at The Bus Stop Cafe, and then afterwards we went back to The High Line to walk the rest of it. Like I mentioned above, this is something I would skip in the afternoon – we wished we would have walked the entire thing in the morning before the crowds came.

If you want your bagel toasted at the popular bagel shops, don’t forget to ask when you order.

Some of the shops like Broad Nosh Bagels asked us when we ordered if we wanted our bagels toasted, but some didn’t ask and assume you don’t want them toasted because traditionally, the bagels aren’t toasted. I forgot to ask at Liberty Bagels and we were a little bummed since I like toasted bagels.

I’ll dive more into specifics / how-to’s in other blog posts, but I think this is a good overview of everything. If you have any specific questions, reach out to me anytime on Instagram; my IG account is @today.with.jess and I’d love to connect with you!