Experiencing NYC In 5 Days

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An itinerary for newbies visiting New York City for five days: what to see and do, where to eat and stay, we've got it all covered.

I grew up going to New York City every year for Thanksgiving. It is a tradition that I hold near and dear to my heart. I have been in love with NYC since my first visit and I fall more in love with it each time that I go.

When my mom (Melody) and I were going to NYC for the New York Times Travel Show, I could not pass up the opportunity to take my husband (Blake) for the first time. I cram packed as many activities as I could into our short stay so that he could experience all of New York City. After 5 days in NYC, he fell in love with the city, too.

*We were only in NYC for 4 full days, but I combined the 2 half days, thus totaling 5*

Here is our five day guide for seeing every nook and cranny in NYC.



For our first night in NYC, we chose to have dinner at Virgil’s, serving traditional BBQ in Times Square. We split the Trainwreck Fries (hand-cut fries covered with melted cheddar and jack cheese, smoked bacon, scallions, and pickled jalapeños with ranch dressing) and the Pig Out Platter (Memphis style pork spare ribs, sliced Texas beef brisket, Carolina pulled pork, BBQ 1/4 chicken, mac and cheese, and hickory smoked baked beans). It made for quite a dinner!

Here is our five day guide for seeing every nook and cranny in NYC.

Drunk Shakespeare

This was one of our favorite activities! Five professional actors meet, one of whom will consume at least five shots, and attempt to perform a Shakespearean play. Together, they form the Drunk Shakespeare Society, meeting in a secret lounge full of more than 15,000 books. This is an experience like no other! Blake and I laughed from the moment we entered until we left. I cannot recommend seeing Drunk Shakespeare enough. The designated drinker and Shakespearean play rotate, so each show is different.



Today Show

Blake and I spent our first morning in NYC at the Today Show’s plaza. Since it was cold and dreary, we did not show up until around 9 AM. Blake and I were pleasantly surprised to only find around 20 people there. When the camera came outside to film, we all huddled together to make it look like there were more people on the plaza. It was fun getting to see a show, that I watch daily, film.

seeing the today show in New York City

NBC Studio Tour

Blake and I absolutely loved the NBC Studio Tour. We met with the rest of our group in the NBC Store, went through security, watched a short film about NBC’s history, and started our walk through Rockefeller Center. Our first stop was to the Saturday Night Live studio. It was tiny! We cannot believe that everything happens in such a small area. Next, we visited the newly renovated studio for Late Night With Seth Meyers. It looks exactly as it does on TV. Then, we saw NBC’s control rooms and made a short film of our own. The NBC Studio Tour was even better than we had expected. This was another of mine and Blake’s favorite activities.

Shake Shack

Pressed for time, Blake and I had dinner at Shake Shack, where the food is good and not super expensive. The line to order was out the door, but we did not mind waiting, plus the line moved fairly quickly. We thoroughly enjoyed our burger, milkshake, and french fries covered in cheese and bacon.

eating dinner at shake shack in New York City

Book of Mormon

I have seen numerous Broadway musicals and this is my new favorite. Book of Mormon was Blake’s first Broadway show and what a way to start out! The cast was incredible. Blake and I loved the music so much that we bought the album when we left. I can see why this production has won 9 Tony Awards, including Best Musical. After the show, we waited at the Eugene O’Neil theater stage door for the actors to leave so that Blake could get his first Playbill signed.



9/11 Memorial

The 9/11 Memorial was even more heartbreaking that we had imagined. There are two reflecting pools out front, sitting in the same spots that the Towers did. The name of each life lost on September 11th, 2001 is inscribed in the Memorial pools’ edging.

This state-of-the-art museum, commemorating the largest foreign attack on US soil, is a powerful experience. You will find an original staircase used to evacuate, missing person posters, first hand accounts of the day, pictures of the rubble and first responders on scene, and pieces of wreckage from the plane crashes. We thought the 9/11 Memorial was incredibly done and are thankful for the opportunity to visit.

Here is our five day guide for seeing every nook and cranny in NYC.

Top of the Rock

My favorite place to see all of NYC is at Rockefeller Center‘s Top of the Rock. Go to the open-air roof deck on the 70th floor for great views. We took some awesome pictures and enjoyed picking out buildings that we knew. Shop for souvenirs of your favorite NBC shows on your way out, as the exit is through the NBC Store.

Here is our five day guide for seeing every nook and cranny in NYC.

Tonight Show with Jimmy Fallon

We were lucky enough to attend a taping of The Tonight Show with Jimmy Fallon. During the first week of December, I applied for tickets, but did not find out we received them until three weeks prior to our trip. NBC gives out more tickets than there are seats; a ticket does not guarantee you a spot in the audience.

We showed up to the NBC Peacock Lounge at 3 PM (as stated on the ticket) to find a line full of people. After an incredibly long check-in process, we were finally led into the Tonight Show’s studio. The studio is much smaller in person than it is on TV and the audience is much larger. Our show’s guests were Drew Barrymore, Tom Brokaw, and the Parquet Courts. Although it was awesome to see Jimmy Fallon, he was not nearly as energetic as I had expected.

Cielo at the Mayfair

We stumbled on this place while walking around the Theater District. What a great find! Cielo at the Mayfair serves authentic Italian food in a very intimate and cozy setting. The restaurant has two floors with separate entrances. In addition to great Italian food, we also had awesome handcrafted cocktails.

Here is our five day guide for seeing every nook and cranny in NYC.


A trip to NYC is not complete without a slice of cheesecake from Junior’s. We stopped by after dinner and had dessert. Even at 10PM, the restaurant was on a wait. Our slices of cheesecake were everything that we had hoped for and more.

Here is our five day guide for seeing every nook and cranny in NYC.


American Museum of Natural History

 Exploring the American Museum of Natural History was a blast. We spent majority of our time in these rooms: the Spitzer Hall of Human Origins, Guggenheim Hall of Minerals, North American Mammals, Akeley Hall of African Mammals, and the whole Dinosaur wing. The Butterfly Conservatory was our favorite special exhibit, although we enjoyed the other three as well (Cuba, Wonders of the Arctic, and Dark Universe).

Blake, a Pediatric Intensive Care Unit nurse, thoroughly enjoyed the Countdown to Zero exhibit. We could have spent an entire day at the American Museum of Natural History reading all of the information provided. What a fun educational experience!


Southern Hospitality

After sitting in traffic for much too long, our cab driver let us out and we ended up out front of Southern Hospitality. We decided to try it out since we were hungry. It was my favorite meal of the trip. We walked in to find a packed restaurant, Bluegrass band playing live music, and a killer menu.

I could not have been happier with my meal: bottomless mimosas plus chicken and waffles. The prices were pretty high, but Southern Hospitality serves the best authentic BBQ in Hell’s Kitchen. Later, we learned that Justin Timberlake is a co-owner. How cool!

Here is our five day guide for seeing every nook and cranny in NYC.

The Ride

The Ride’s slogan is “experience The Ride” and this attraction is just that, an experience. We boarded the coolest bus that I have ever seen, with seats like a theater and flashing lights. The bus has a voice that chimed in throughout our journey around Times Square. We encountered a Radio City dancer, package delivery man, and ballet dancer who all performed for us. This is definitely for those who want to be entertained!

Here is our five day guide for seeing every nook and cranny in NYC.
Photo from.

Ice Skating at Bryant Park

What is a trip to NYC without ice skating? Blake and I chose to ice skate at Bryant Park’s Bank of America Winter Village. Although admission to the rink is free, skate rentals are $20 per person. We did not stay long, but what a great experience.

Here is our five day guide for seeing every nook and cranny in NYC.

Empire State Building

Visit the Empire State Building and see all of New York City from the 86th and 102nd floors. We went at night, allowing for a different view of the city as everything was lit up. The theme of the Empire State Building experience is classic 60’s. We enjoyed looking at all of the themed decorations.



Central Park Zoo

While Melody and I visited the Javits Center for two events, Blake went to the Central Park Zoo. He absolutely loved it! Blake got to see lions, a snow leopard, bears, and a red panda. He opted to add the 4D theater show to his ticket. The zoo is full of informative facts and he recited many of them off to us when we met up for lunch. Blake highly recommends this NYC attraction to all animal lovers.

Here is our five day guide for seeing every nook and cranny in NYC.


Melody and I started our day at the second annual BroadwayCon, taking place at the Javits Center. The exhibit hall had booths set up selling Broadway gear, while people dressed up as their favorite character walked around singing show tunes. Another room had panels set up for Q and A sessions with casts of Broadway shows. It was a lot of fun. A Playbill background allowed us to create our own Playbill cover. What a cool event for Broadway lovers!

Wherever i May Roam visited NYC's Broadwaycon this year.

Cirque du Soleil’s Paramour

Paramour is Cirque du Soleil’s first attempt at a Broadway show. I absolutely loved it: the live music, singing, storyline, dancing, and famous Cirque du Soleil acrobatics. Paramour tells the story of a famous Golden Age Hollywood director looking for his next big star, whom he falls in love with. I thought this Lyric Theatre production was very well done. The only thing missing was a Playbill.

Have you seen Cirque du Soleil's new Paramour show?

Ray’s Pizza

Ray’s has been a New York staple since 1980, serving the best pizza in the city. We stopped by so that Blake could have his first slice of New York pizza. He raved about it!

Here is our five day guide for seeing every nook and cranny in NYC.

Gaby Restaurant

While in New York city, we stayed at the Sofitel and could not have asked for better accommodations. The location was perfect, the hotel is absolutely gorgeous, and our room provide all that we needed and more. We ate at the Sofitel’s Gaby Restaurant on our last night in town.

Everything that we had was wonderful: French Onion Soup, Caesar salad, Cold Water Maine Lobster Tail, White Chocolate Mousse, Asparagus Salad, and Vegetarian Lasagna. Our meal was so wonderful that we could have eaten here another night.

Here is our five day guide for seeing every nook and cranny in NYC.


Metropolitan Museum of Art

Visiting the MET was the perfect way to end our trip. Although the museum was a bit challenging to navigate, we had fun exploring the galleries. Our favorite artists were Vincent van Gogh, Claude Monet, and Mary Cassatt. Our favorite work of art was “Washington Crossing the Delaware” by Emanuel Gottlieb Leutze. It was massive, beautiful, and the perfect way to end our time in NYC.


I Love NYC

We enjoyed every second of our 5 busy days in New York City. I am so glad that my mom and I got to show Blake around a city that means so much to our family. He truly got to experience NYC.

Until next time, New York City.

Here is our five day guide for seeing every nook and cranny in NYC.

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experiencing New York City in five days itinerary
Here is our five day guide for seeing every nook and cranny in NYC.

Thanks to all for making this trip possible: The Sofitel, CityPASS, Drunk Shakespeare, American Museum of Natural History, The Ride, The Tour at NBC Studios, and Broadwaycon. As always, all reviews and opinions are unbiased and completely my own.

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