I have dreamt of walking the streets of New York City my entire life. 

This electric city is the backdrop to so many of my favorite films. So, of course the only things I knew about New York were from the movies – hailing cabs, eating street food, strolling through Central Park, grabbing coffee for your boss before work – you know the ones. 

On October 3, 2019, my husband Joel and I will celebrate five years of marriage. I knew I wanted to celebrate our anniversary in a special way, so I began researching a New York City vacation. The probably-too-good-to-be-true trip became more and more real as all the details began falling into place.

I read many helpful blogs and articles when planning our trip, so I decided to share the details of our little 4-day getaway. This is a day-by-day guide followed by pizza ratings and a list of helpful tips!

Dates: July 23 - 27
Where we stayed: Brooklyn, NY (with a friend, thanks Delia!)
Prep before the trip: I did a lot of research beforehand and made a list of the things we were interested in seeing and doing. This helped tremendously when it came time to plan our days.
How we got around: We each purchased a week-long metro pass for $33 which gives you unlimited rides for seven days. With the subway being our main method of transportation, it would have been more expensive to pay per ride. I highly recommend downloading the CityMapper app when you arrive. It was helpful when looking for the quickest routes by train. We used Apple Maps for directions walking from place to place.


After dealing with a cancelled and rescheduled flight, we landed at JFK around 11am. We took a Lyft to Delia’s apartment in Brooklyn and, after getting settled, were eager to see the city.

Her apartment was a short walk to a subway station and about a 40-minute ride to Manhattan (time on a train passes so quickly). Delia helped us get our Metro cards at the station and told us which train to get on –  of course we walked right down the stairs and took the wrong one! It was a great mistake, though, as we got off at a stop near Washington Square Park.

I fell in love with the city immediately. The perfect blend of buildings and trees. The colorful people. The hustle and bustle. It was absolutely stunning.

We saw the Washington Square Arch on our way to eat pizza at John’s of Bleecker Street. (Before I continue, you must know that Joel’s goal was to try as many slices of pizza as he could – and of course I didn’t mind.) We devoured an entire pie and it was delicious. It only took one bite to finally understand why New York is known for their pizza. It’s the best. It just is.

We stopped at a little bakery called Milk & Cookies and ate the most perfect chocolate chip cookie on our way to the Friends Apartment, which is located in Greenwich Village. The walk from there to the Flatiron Building was surreal. Gorgeous homes. Cute coffeehouses. Great window shopping. And, casually passing the Empire State Building on our way – no big deal. We sat on a bench in Madison Square Park, Flatiron Building in plain view, and just took it all in.

I could honestly sit on a park bench in New York for hours. There are so many people doing so many things. Reading. Strolling their children. Running. Talking on the phone. Ordering street food. Walking their dog. Meeting up with friends. Listening to music. Drawing. Sleeping. Playing games. It was fascinating.

From there, we hopped on a train (the right one this time) to Williamsburg to meet Delia. We walked around an area called Domino, saw the Williamsburg Bridge and ate dinner at a cute little Italian restaurant called Patrizia’s near the water in Williamsburg – I recommend the spaghetti & meatballs.

I went to bed both exhausted and eager to explore some more the next day.


We started our second day with breakfast at Sarabeth’s Central Park South. (And quite honestly, every day should start with breakfast at Sarabeth’s.) We ate the most delicious french toast and then walked around the corner to The Plaza Hotel. After I had my Eloise moment, we strolled into Central Park.

Central Park was honestly breathtaking – and huge! We admired bridges and lakes and pathways and flowers. We walked until we found the perfect tree to sit under and had a dreamy moment reading, listening to music and people watching.

We made it to other side of the park, ate a Sabrett hot dog and went to the American Museum of Natural History. They have a suggested entrance fee, but you can pay what you want to get inside. The museum had interesting artifacts, but was fairly crowded with children on field trips. Our favorite parts were the dinosaur and ocean exhibits, but we agreed we would probably not go back if given the opportunity. After our time at the museum, we split a bagel at Bagels & Co. and walked to Cafe Lalo (where they filmed this iconic You’ve Got Mail scene) just to peek inside.

We made our way to Times Square – which was everything you’d expect – loud, bright, exciting, busy. We took selfies like any good tourist and walked toward Rockefeller Center to shop at FAO Schwarz. What kind of parents would we be if we didn’t pick out a present for our baby girl?

On our way to dinner, we passed Radio City Music Hall and walked through Times Square again. We had reservations at Sardi’s, which was lovely and a delicious break from pizza and street food. (Make a reservation online beforehand if you plan to go. It’s a great pre-show meal.)

Our next stop was the New Amsterdam Theatre to see Aladdin: The Hit Broadway Musical. At the risk of sounding dramatic, I have waited for this bucket-list moment for years: a real New York Broadway show. And, it did not disappoint. The costumes, the sets, the songs, the magic carpet ride – it was all such a dream come true.

Walking out of the theatre into Times Square, the flashing lights and number of people would have made you guess it was the middle of the day. Of course we had to stand in line at Joe’s Pizza for a slice and grab ice cream cones from Ben & Jerry’s.

This was my absolute very favorite day.


We had a quick coffee-and-banana-bread breakfast from Brooklyn Perk (super cute coffee shop), walked to Prospect Park (a great park if you’re staying in Brooklyn) and stumbled on The Boathouse. We finished our coffees on the steps of The Boathouse and enjoyed the gorgeous views.

Then we rode a train into the city to meet my childhood best friend for lunch. We felt like locals walking through an alleyway to our hidden destination – Freeman’s Restaurant. After good food and great conversation, we grabbed another quick slice of pizza at Prince Street Pizza, and headed south to catch the Staten Island Ferry.

When we got off the subway, we were in the Financial District – totally unplanned! We walked by Wall Street and the New York Stock Exchange to get to where the ferry departs. I highly recommend riding the ferry if you have time. It’s free and if you stand on the right side, you have a beautiful view of the Statue of Liberty as the ferry moves away from Manhattan.

After the relaxing ferry ride, we made our way to Chelsea Market to get coffee and walk the High Line all the way to the Vessel at Hudson Yards.

Our main event this evening was seeing John Mayer at Madison Square Garden. We grabbed a quick sandwich from Gardenia Deli and felt like locals while we ate on the steps of Penn Station. After our delicious sandwiches (literally everything in New York tastes amazing), we went into MSG to see Mr. John Mayer – an incredible show! We had to grab pizza afterward, so we ate at New York Pizza Suprema right outside of MSG before taking a train back to Brooklyn for some much-needed rest.


We wanted to have a slower morning in Brooklyn on our last day, so we walked to Milk & Honey for brunch. The gorgeous walk from Delia’s apartment to Milk & Honey is through an area called Victorian Flatbush – one of the largest collections of Victorian homes in the country. We had a lovely brunch at Milk & Honey and headed into Manhattan for the last time. (Cue the sadness.)

We hadn’t had greek yet, so we grabbed a gyro pita from a street vendor. It was so delicious that we immediately regretted not ordering one of these every day! We popped into Strand Bookstore and then grabbed yet another piece of pizza at Sauce. I had heard nothing but great things about the frozen hot chocolate from Serendipity 3, so we had to see for ourselves – and, yes, it was delicious!

One of our favorite things was Central Park, so we wanted to go back but to a different area. We walked by the Jacqueline Kennedy Onassis Reservoir and then relaxed on The Great Lawn before heading to our scheduled Superhero Tour. (I booked this through TopDog Tours as a Father’s Day gift for Joel. Worth every penny!) On the tour, we saw so many buildings that were either filming locations or set inspirations for Spider-Man, Batman, Daredevil, the Avengers and more! Here’s a list of a few of the tour highlights:

  • United Nations Building

  • Osborn’s apartment (from Spider-Man) in Tudor City

  • The Daily News building

  • Chrysler Building

  • Grand Central Terminal (where they filmed this entire scene in Avengers)

  • Marvel Comics’ first office

We ended the tour at a comic book store, JHU Comics, so we had to get an issue of an old Spider-Man comic – Joel’s favorite! We went back inside Grand Central and, I’m proud to say, we navigated our way to take the right train back to Brooklyn. (GCT has 44 platforms, more than any other railroad station in the world.)

We had reservations at Grimaldi’s Pizzeria in Dumbo, Brooklyn, but weren’t huge fans, so we found a nearby place with great reviews called Ignazio’s. We ate our slices under the Brooklyn Bridge and then headed to walk the bridge at sunset. I couldn’t think of a more perfect way to spend our final night.







  6. SAUCE


This was a trip of a lifetime.

I knew we would have fun, but I honestly did not expect to fall in love with the city as much as I did. I was sad to leave and am still anticipating the day I can return – hopefully with my little girl!


  1. Pack a wireless phone charger. Someone told me this before we left and it was a life saver. Our batteries drained from using our phones for pictures and directions.

  2. Don’t be afraid to ask for directions. Everyone we talked to was super friendly and happy to point us in the right direction.

  3. Plan your days wisely. Figure out what you know you want to do, map out those locations and plan to do those things on the same day to save time.

  4. Don’t over-schedule. Try to allow time for rest – whether that means sitting on a park bench, reading at a coffee shop or going back to your hotel for a quick nap. We were very go-go-go and regret not building a little more rest into our days.

  5. Two words: comfy shoes. With the amount of walking we did, there was no way my sandals would have cut it. It’s “next level” walking. I wore my comfiest cute blush tennis shoes almost every day.

  6. Not every pizza place sells by the slice. Some places make you buy a whole pie. You might want to call or check online before going.

  7. Pack one outfit for the day. This was hard for me, but because we stayed farther from Manhattan, it didn’t make sense for us to waste time traveling back to where we were staying to “change for the night.” So, I had to think about what I would be comfortable wearing to multiple types of settings (i.e. parks, museums, concerts, restaurants). A dress or romper with tennis shoes was my go-to.

  8. Prepare to walk – a lot. It wasn’t strange for us to walk 20,000+ steps per day. We didn’t want to spend a lot of money on cabs, so we walked or took trains everywhere. Maybe schedule a pedicure on your last day, too – your feet will thank you.

  9. Trains aren’t always reliable. Sometimes the trains “run differently” at night (or they undergo maintenance). If your app is telling you that the train is running differently, it’s okay to have NO IDEA WHAT THIS MEANS and ask for help (or just take a cab). I don’t know what I would have done without Delia!

  10. You won’t see it all. I had to repeat this to myself over and over (and over) going into the trip. I had never been to NYC, so my list of must-do’s was a mile long. I had to tell myself that there would be things we could not get to. Even New Yorkers haven’t done everything in New York. The city is so big and has so much to offer. I tried to focus on the things we did get to do, and as for the things we didn’t? Well, we will just have to go back.

One belongs to New York instantly, one belongs to it as much in five minutes as in five years.
— Thomas Wolfe