New York City-The City That Never Sleeps

When most people think about the biggest city in the world, they immediately think of New York City. Of course, this is not logistically accurate, but to the mind’s eye it most certainly is. With that knowledge comes a small level of both intimidation and excitement.

NYC skyline from the rooftop of our Airbnb, New York City, NY.

We want to remind everyone that we started this blog for a very simple reason; to get the word out that you do not need to have a thousand trips in your back pocket to have the confidence necessary to tackle any destination. We are not experts by any stretch of the imagination. Unfortunately, we do not have friends in every port just waiting for our arrival to be our personal guides. We are both in our 40’s (give Jen a moment to take a deep breath at that admission) and only began seriously traveling a few years ago.

You have to start somewhere. Take that initial leap and dive in. Do not let fear hold you back. You only regret the things you do not do, never the things you do. We promise you that with a little bit of planning and research you can plan a trip to any city. Sometimes getting a little lost is the beginning of the best adventures.

In our most recent podcast (available on iTunes), we spent the beginning talking about New York City. We realized that we hadn’t written a blog post about this incredible place yet. How did that happen?! Let us begin with a little personal background with the city.

Skyline from the roof of our Airbnb, New York City, NY.

Prior to our stars aligning, we both lived in different parts of northern New York (not Albany, try four hours north of that.) For both of us it was at least a six-hour car ride into the city. Craig had been a few times for work trainings and Jen had been for one crazy afternoon with a hockey team. Neither one of us had the opportunity to really submerge ourselves into any part of the area. Honestly, you could spend a month there and not see every nook and cranny.

Fast forward, stars aligned, we say I do, and we are taking a family trip to New York City for spring break. We take on the highlights of the Statue of Liberty, Ellis Island, Museum of Natural History, Yankee Stadium, the Amish Market (oh my God amazing), and the best bagel shop ever. While we had an incredible time, we still only saw a small fraction of the city.

This was in part due to Jen’s comfort level. With kids in tow, she did not want to overwhelm them or lose the one wanderer of the group (if you are reading this, you know who you are.) One thing with travel, the more you do it the more comfortable and confident you become. Craig and Jen made a promise to return soon.

Planning New York City

We are going to begin by tooting Craig’s horn a little. He has his own hashtag, given to him by friends of Jen. #WhatWouldCraigDo. Next to know is Jen’s favorite movie is Moulin Rouge. When we say favorite, we mean she has watched it at least one hundred times (no exaggeration, she burned through a DVD and had to replace it) and can recite the entire thing. Also, she has always wanted to see a play in the city. Always. So, what does Craig buy Jen for her 40th birthday….tickets to watch Moulin Rouge at the Al Hirschfeld Theatre in New York City. #WhatWouldCraigDo.

This was one of those trips that he planned completely on his own without our handy dandy planning journal. Look at us being spontaneous! Sort of. A little bit. Well, he did not have a few hours of our afternoon planned, so just follow along with us here.

Grand Central Station, NYC, NY.

Who doesn’t love a weekend away to a vibrant city full of life? No matter where you live there is a city available to you for a quick getaway. Every city has something to offer for any palate. Ours happens to be theater, which makes New York City perfect for us. Remember, you know what makes you happy and what to plan for. Find your thing and start your search.

Craig had a plan for Jen’s birthday and signed up for Broadway notifications. The fateful ping hit his phone informing him that Moulin Rouge was opening and tickets were available. He did what any sensible, loving husband would do and bought his wife the tickets. Now that the main event was ready, we just needed lodgings.

The city has so many options when it comes to accommodations. We have found luck with Airbnb. Depending on your destination this can be a little cheaper and get you closer to where you want to be. He chose an apartment directly across from the theater on W 45th Street. This was incredibly convenient since the show was ending just before midnight and we would not have to venture through the city streets in the middle of the night if we didn’t want to.

The final step for us, which is optional to everyone else, was buying the tickets for the commuter train from Poughkeepsie to Grand Central Station. We know our comfort level and what will make things flow a little smoother for us. While Craig has driven in the city before, choosing to park the car at the station lifts a little of the stress off his shoulders.

Craig and Jen on the train into NYC.

On a side note, for some reason, every time we are in Grand Central Station we stop for a chai latte in the coffee shop downstairs. It doesn’t matter if we are arriving or departing, the first, or last, thing we do is get a chai. It’s funny the habits you fall into.

That was it for the planning- Main Event tickets, a bed to sleep in and train tickets. We were heading out early Saturday morning and returning late Sunday night. We were ready for our unforgettable trip!

For those of you that need a little more planning, you can map out the way from the station to your hotel or you can even just plan to take an Uber or one of the hundreds of taxis you will see right outside the station. If possible, we love to walk. For us, it allows us to immerse in the life, the sights, the sounds, and the smells (maybe not that last part….especially in summer!)


When we arrived in early afternoon, we began our half mile trek to W 45th Street. As we mentioned before, we are not New York City experts and did not realize the frequency of street fairs. So, when we stumbled upon one of the Manhattan Street Fairs it was an extra birthday present for Jen. She spun around like Julie Andrews on the hills of Austria, it was quite the sight. Isn’t that the best part of travel though? The unexpected treats thrown in to make everything better than you imagined.

Times Square, NYC, NY.

We raced to our apartment to drop off our bags and get right back to the action. We strolled leisurely along the various vendors snapping up some trinkets and food to sate our appetite. After a while we wanted to relax and people watch. We passed by a bar with a sign pointing to a roof top bar. Our eyes met and without words we headed to the stairs. We grabbed the last available table, got our drinks and enjoyed each other’s company while watching life unfold below.

Soon it was time to doll up for the show. We enjoy dressing up for a night out and if that is your thing, this might be the perfect place for you too. Craig was looking dapper in his suit and tie and Jen brought her little black dress with the perfect heels. A bit of advice that we stumbled upon, be ready to wait in line. Luckily we were there in September, so the weather was mild. We waited about twenty minutes outside, so if it had been winter, we might have altered our clothing a little.

Moulin Rouge

The Al Hirschfeld Theatre, New York, NY.

Finally, the doors opened, and we were able to do a little wandering. You do not have to go early like we did, but Jen is a little neurotic about being early to things. Movies, shows, sporting events, you get the idea- early. There is a reason though. We like to look around a little and get a feel for the architecture and its history. This theater was built in 1924 and you can see it in the well-maintained design. I mean, Elizabeth Taylor performed here. Go early and just soak that in.

It also gives you time to appreciate the set and the incredible detail and craftsmanship that has gone into making this come to life. The set for Moulin Rouge was breathtaking. We cannot put into words what it felt like to be there. Jen’s feet never hit the ground and Craig’s chest was puffed out like a peacock because he knew he won the best birthday present ever contest. Hands down.

We watched Karen Olivo and Aaron Tveit bring Satine and Christian to life in front of our eyes. We sang along to every song and took in every moment. It was an incredible performance that we will never forget.

As are most things in life, all too soon it was over. We stopped at a corner pizza place and had a late-night snack trying to come down from the experience that was that show. Looking around, we enjoyed the bustling life that was still filling the streets at midnight where our sleepy little town would be quiet in the night. We savored the cool air as we walked back to crash for the night.

For those of you that do not think you could walk along the streets for fear of getting lost. We had our GPS going on our phones in walking mode and the streets in New York City are conveniently straight and numbered making it almost impossible to get lost. You can do it, we promise!

View from our rooftop bar, NYC, NY.

No trip to New York City is complete without a bagel. Find a shop with a line and hop in it. Be ready with your order and possibly cash, as we have found a few are cash only. Fresh bagels with freshly made cream cheese- sign us up. We need to find a friend down there to send us weekly shipments! This is probably Craig’s favorite part of the trip; walking the streets of the city, eating an authentic New York City bagel with a cup of coffee. Yes, please.

With full bellies and delirious smiles, we left Grand Central Station with another adventure and more moments to treasure. And a chai. Book the trip.

What has your experience in New York City been like? Tell us below.

Thank you for reading, and remember #NeverStopPlanning.

Jen and Craig

3 thoughts on “New York City-The City That Never Sleeps

  1. I went to NYC many, many years ago. Having lived in a rural setting all my life, the big city was a little daunting. Seeing the city through your eyes, makes me want to visit again!

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