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There’s something magical about wandering through the bustling streets of New York City, especially for couples eager to create unforgettable memories together. Dan and I found ourselves returning to this iconic metropolis two and a half years after our last visit, filled with excitement to relive old favorites and explore new gems. This time, we set our sights on diving into the vibrant theatre scene and savoring delicious meals, all while uncovering the city’s hidden treasures.
With the end of an era approaching—the final episodes of The Late Show with Stephen Colbert airing in May 2026—I decided to surprise Dan with tickets as a Christmas gift. Our four-day itinerary was designed to maximize every moment in the city that truly never sleeps.
Finding Our Home Away from Home
On our last trip, we indulged in the luxury of the Plaza Hotel, but this time, we craved a different experience. With our packed schedule of shows, we prioritized convenience and chose the Hyatt Place New York Midtown South. This hotel turned out to be a fantastic choice, ideally located for easy access to various theatres. It surprised us with spacious accommodations, complete with a cozy couch and stunning views of the Empire State Building.
The icing on the cake was the complimentary breakfast—hearty and satisfying enough to fuel our adventures. Clean, affordable, and perfectly situated, this hotel is an excellent base for couples or families eager to explore the city.
Packing for a Winter Wonderland
Winter in New York requires thoughtful packing to stay warm and stylish. I always create a visual packing list to ensure I don’t forget any essentials, especially since we were braving some seriously chilly temperatures. Here’s a peek at what I packed:
Clothing Essentials
To fend off the cold, I brought along fleece-lined tights that layered perfectly over my wool base layers. On those particularly frigid days, they kept me snug while still looking chic. My favorite matching wool skirt and sweater set became my go-to outfit, balancing elegance and comfort effortlessly.
Footwear is crucial, and my trusty Chelsea boots were the only pair I needed. Their versatility and comfort made them perfect for the nearly 20,000 steps we logged each day. For our flights, I opted for travel pants and a cozy sweatshirt, ensuring I stayed comfortable from start to finish.
A Whirlwind of Experiences
Our New York adventure kicked off on a Tuesday afternoon, landing at JFK and quickly settling into our hotel. Determined to make the most of our first evening, we initially planned to dine at Via Carota. However, a delay in our DoorDash order led us to snack on treats from the hotel before heading to our first show, Maybe Happy Ending.
This enchanting performance featured retired personal robots navigating the complexities of friendship and love through whimsical storytelling. It was a delightful surprise, blending humor with emotional depth in a way we hadn’t anticipated.
Exploring the City Together
After the show, we took a leisurely stroll through Rockefeller Center, soaking in the post-holiday ambiance on Fifth Avenue. Our second day began with a relaxing morning, allowing us to recharge before indulging in lunch at Ahimsa, where we enjoyed flavorful South Indian cuisine. The highlight of our day, however, was finally attending Stephen Colbert’s live show, where we laughed along with him and special guest Paul Giamatti.
Connecting with History and Culture
With the end of an era approaching—the final episodes of The Late Show with Stephen Colbert airing in May 2026—I decided to surprise Dan with tickets as a Christmas gift. Our four-day itinerary was designed to maximize every moment in the city that truly never sleeps.0
Reflecting on Our Unforgettable Journey
With the end of an era approaching—the final episodes of The Late Show with Stephen Colbert airing in May 2026—I decided to surprise Dan with tickets as a Christmas gift. Our four-day itinerary was designed to maximize every moment in the city that truly never sleeps.1
With the end of an era approaching—the final episodes of The Late Show with Stephen Colbert airing in May 2026—I decided to surprise Dan with tickets as a Christmas gift. Our four-day itinerary was designed to maximize every moment in the city that truly never sleeps.2