Grand Central Terminal's main lobby and iconic clock.

The iconic clock at Grand Central Terminal, a timeless symbol of New York City.

If you’re seeking a self-guided tour of NYC that blends iconic landmarks with artistic treasures and delectable cuisine, this itinerary is for you. Within a three-mile radius in Midtown Manhattan, we’ll uncover hidden gems and beloved favorites, providing a perfect balance of indoor and outdoor activities (and to get a break from the weather or walking). 

If you’re interested in a specific place, click the link below or continue scrolling to read about each one. You might even learn some historical facts along the way!

Grand Central Terminal

Our journey begins at the iconic Grand Central Terminal. Despite countless visits, I’m still captivated by its stunning architecture and rich history dating back to 1913. The famous clock in the center of the terminal to the iconic zodiac ceiling that was painted backward (yes, you read that correctly) continues to mesmerize onlookers. Did you know Grand Central Terminal may not be here today if Jackie Kennedy Onassis hadn’t saved it? 

Beyond the main concourse, Grand Central Terminal offers a world of hidden treasures with restaurants, shops and less obvious hidden secrets like the “whispering gallery" on the lower level. The arched ceiling in front of The Oyster Bar is where you’ll find this hidden gem. It takes two people to experience this magical wonder by standing diagonally from each other, facing the corner walls, and talking in a normal tone. You can share your secrets as your voice travels across the ceiling to the person on the other side.   

Grand Central Terminal's main entrance on Park and 42nd.

Architectural grandeur at the main entrance of Grand Central Terminal.

Cafe Grumpy

Starting our day with a pick-me-up, we head to Cafe Grumpy in Grand Central Terminal. This is one of our favorite coffee shops in NYC for a delicious cappuccino. It’s been independently owned since it opened in 2005. They have multiple locations in and around NYC. Their logo perfectly captures how I feel sometimes before having that cappuccino or actually latte, which is my preference. After just one sip of their brew, the fog lifts and my mood does a 180!

The Grand Central Terminal location is a cozy atmosphere perfect for people-watching while enjoying our favorite cup of joe. 

Grand Central Market

Just steps away from Cafe Grumpy lies the Grand Central Market. It’s surprising to say a market could be hidden, but Grand Central Terminal covers three city blocks and has several entrances and exits.

This vibrant market is a treasure trove of local vendors dating back a century-old offering delectable chocolates, pastries, fresh meats, seafood, cheese and more.

Stop in to look around or pick up something for later. 

The Perfect Pint

For lunch, we head to another hidden gem called The Perfect Pint. We have walked past this pub so many times that we had to give it a try. It was beyond our expectations! The real hidden gem is their rooftop, which I usually jump at the chance to dine outside on a beautiful day. Making our way to the rooftop, we were surprised to pass two other levels with more seating for overflow or private events. There is also a bar on each level. Once we reached the rooftop, we were transfixed! 

The decor recreates seating outside a traditional Irish Pub with thatched roofs and walls made of brick and wood planks. The thatched roofs shade the side tables while the ceiling of the rooftop opens up, letting the outside into this patio-like pub. The transformative vibe continues with tables and chairs made with whiskey barrels and kegs. There’s also an open terrace with a few seats to enjoy the sights and sounds of NYC.

Being an Irish pub, we had to try the fish and chips and a Guinness on tap, which may have been the best I’ve ever had. The Perfect Pint has over thirty beers on tap, including their own brews. I don’t opt for beers that often, but when I do, I prefer them on tap. There’s nothing fresher, and creamier in the case of a Guinness, than a beer on tap. The staff was so friendly, making us feel welcomed from the start, and attentive to ensure we enjoyed our meal. 

I highly recommend this restaurant and its rooftop to enjoy the outdoors, the views, and delicious food. This is also a great spot for after-work get-togethers. 

Museum of Modern Art (MoMA)

After a satisfying lunch, we delve into the world of art at The Museum of Modern Art (MoMA). Three influential women - Lillie P. Bliss, Mary Quinn Sullivan, and Abby Aldrich Rockefeller - saw a need to have a museum for modern art in the 1920s. Thanks to their vision, modern art has found a vibrant home in the heart of New York City.

MoMA has over five floors of exhibits, including a sculpture garden. For those who enjoy the outdoors, this may be the perfect time to take a break in the garden while appreciating the beautiful sculptures. There’s a museum store on the lower level and across the street.   

If you enjoy artistic and timeless furniture, the “Crafting Modernity: Design in Latin America, 1940-1980” exhibit is worth seeing. Head there before it’s gone – the showing is through Nov 10.

Ralph’s Coffee

As the day progresses, we’ll need a caffeine boost to keep us going. This time we stop at another coffee favorite in NYC – Ralph’s Coffee. For those unfamiliar with this brand, it is Ralph Lauren’s coffee. The first Ralph’s Coffee opened in NYC on Fifth Avenue and 55th in 2014. Over the years, we enjoyed several cups of coffee at that location, but sadly it closed. No fret, though, since Ralph’s Coffee can be found at many locations throughout the world.

Today’s stop is at Ralph’s notable mobile coffee truck at Rockefeller Center. Stepping back in time, we order from a replica of a 1943 custom-built vintage Citroen coffee truck. We sip on a cup while enjoying the outdoor cafe seating surrounded by more history. The Atlas statue, built in 1937, is among the seating and St. Patrick’s Cathedral, opened in 1879, is across the street.

It’s a surreal experience to sip coffee amidst these towering historical landmarks, a reminder of the city’s rich past and its vibrant present. 

Bryant Park Cafe

Still enjoying the beautiful weather while it lasts, we make our way to one of our favorite summertime restaurants - Bryant Park Cafe. Just behind the New York Public Library, this charming outdoor cafe provides a peaceful oasis in the heart of the city. The sizable bar is perfect for grabbing drinks with friends or colleagues after work. Seating in the restaurant and bar are first come, first served. So, get there early to avoid crowds. Tonight a band was performing in the park, which was a harmonious backdrop while dining under the stars.  

The park has gone through many transitions since it was designated a public park in 1686. It was the former site of the Crystal Palace, a glass and steel hall built in 1853 for the first World’s Fair, and later burned to the ground in 1858. It was also a battleground for George Washington’s troops in 1776.  

During the winter, the cafe turns into a Winter Village Curling Bar. Visitors can warm up in a heated dome (available for rent) while cooling down curling on iceless lanes.  Bryant Park is a year-round hub of activity, with something to delight everyone. Be sure to check the calendar and see what’s in store.  

Reflecting on Today’s Exploration

As the moonlight shined brighter and the music was winding down, we reflected on our day of exploration. From the architectural marvels of Grand Central Terminal to the culinary delights of The Perfect Pint, our journey offered a perfect blend of art, history, and unforgettable experiences. Whether you're a seasoned New Yorker or a first-time visitor, this itinerary provides a glimpse into the heart and soul of the city.

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Travel Tips

  • View the map with these locations and add some of your favorites.

  • Bring a durable bag to hold a water bottle and purchases along the way (our choice is Levi’s denim bag).

  • To avoid crowds:

    • Visit MoMA on weekdays

    • Stop at The Perfect Pint weekdays, mid-afternoon

    • Arrive at Bryant Park Cafe before 6pm

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My Durable Levi’s® Denim Bag & Izzy in NYC!