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Dan and I did a NYC couples’ trip about 2.5 years ago that we absolutely loved – we visited some museums, libraries, and hidden gems, and ate some delicious food. It was such a fun time!
The Late Show with Stephen Colbert is one of Dan’s absolute favorites that he’s loved for years, and it’s ending in May of 2026, so I really wanted to get him there to see it live. So for Christmas, I decided to plan another New York couples’ trip for us! This time, I decided to focus on some really special theatre experiences, also eat some great food, and a few other hidden gems we hadn’t visited before.
Here’s everything we did on our 4 day New York City itineary for couples!
The last time we visited, we stayed at the Plaza Hotel with a great deal that we found. It was beautiful and sumptuous and we loved it. This time, we opted to book somewhere super convenient, especially since we were attending so many shows. We ended up booking a room for 4 nights at the Hyatt Place New York Midtown South and loved it. It was the most convenient location – super easy to get to theatres (we just walked), uptown, downtown, to Brooklyn, and anywhere in between. Plus, it was affordable, super clean, spacious (we even had a couch in our room – a rarity in New York!), it had a great free breakfast, and we were even upgraded to a room with absolutely stunning views of the Empire State Building. It wasn’t super fancy but it was honestly perfect and I’d highly recommend it for couples or families, especially if you’re planning to be out and about a lot.
I mostly packed for this trip with items I always take – I always use this visual family packing list even when traveling solo or just with Dan. It’s so helpful to ensure I don’t forget things! Here are some of the clothes I took:
We spent about 4.5 days on our New York City couples’ trip. We flew from London on a Tuesday early afternoon for a scheduled arrival to JFK around 4:00pm (we ended up arriving about 45 mintues early!). Here’s everything we did when we landed!
On our first day, we took the AirTrain + the subway from JFK into Midtown and headed to our hotel. It was very easy to get to and it felt nice to sit and relax for just a bit before heading out. Our room was surprisingly spacious by NYC standars and they’d upgraded us to a high floor, so we had both a couch and a phenomenal view of the Empire State Building out our window!
We knew we wouldn’t quite have time to get over to eat at Via Carota, which we loved on our last visit. We knew it wouldn’t be quite as good, but decided to order DoorDash for it instead. Unfortunately, it was delayed and didn’t arrive before we needed to leave for our show, so we just had some snacks (that the hotel had left for us!) and then walked over to see Maybe Happy Ending. It was SO cute! It’s all about these lifelike personal robots that are retired and develop a surprising friendship of their own. Lots of themes of what constitutes friendship and love, the place for technology, when relationships are worthwhile, and more. The music was great and it was very sweet, and also deeper than we anticipated. We loved it!
After the show, we decided to take a little stroll. We walked over to Rockefeller Center (where the Christmas tree had just been taken down 2 days before, bummer!), down 5th Avenue, and through Bryant Park back to our hotel. We finally ate dinner and headed to bed after a long night.
On our first morning (2nd day) in New York, we slept in! It was glorious. We did manage to get up just before breakfast ended at 9am to go eat, then caught up on a few things in the morning. We headed out for lunch at Ahimsa for some South Indian food (it was quite good! Not destination worthy, but good if you’re close) and then over to queue up to see Stephen Colbert! Since this was the number one impetus for our trip, we wanted to be plenty early and lined up around 1:45pm. We had discussed the trip with another couple who are friends of ours with whom we’ve been trying to plan a couples’ trip, and they were happily able to come and met us in the queue. It was absolutely incredible!
We saw Paul Giamatti and the day we were there and it was such a fun experience. So fun to hear Stephen in real life and even a couple little bloopers. He seemed SO nice and everyone there seemed genuinely happy to be working there. We were a bit devastated that we missed seeing Yo-Yo Ma by only one day, but still so happy we got to go!
We left Colbert around 6:45/7, which was earlier than we anticipated, but our dinner reservations at Shukette weren’t until 9:15pm when I checked the week before. That was the only availability when I checked, but it came SO highly recommended by multiple friends that we were willing to wait. So instead, we walked all the way down, checked in (they couldn’t seat us early), and then walked some more until it was time for our reservation. Well, it was worth the wait!!! Truly one of the best meals of my life – all the veggies and breads and dips were SO good and flavorful. Highly recommend!
After that, we walked back to our hotel and crashed into bed.
The next morning we slept in a bit before meeting our friends + some other friends who live in New York for brunch at Thai Diner. My friend who lives there is a major foodie and recommended it and it was yummy and we mostly loved seeing some of our favorite people. The Thai items seemed better than the others, so I’d order those if you go. Fun, casual vibe, too!
After that, we walked over to the nearby Tenement Museum. I’d visited there years ago but Dan and our friends had never been. We booked the Women of 1902 tour and it was absolutely fantastic – our tour guide was a historia and so knowledeable and explained things in such an interesting, clear, thoughtful way. It was inspiring thinking of the immigrants who worked so hard, were scrappy and clever, and who supported one another through the journey. Highly recommend this tour!
After our tour, we did our own little food walking tour of the Lower East Side. We popped into Shu Jiao Fu Zhou for some dumplings and veggie hot & sour soup, Economy Candy for some American sweets for our kids, Rice to Riches for rice pudding, Katz’s Delicatessen for a sandwich, Il Laboratorio del Gelato for some delicious ice cream (we had the cucumber, which was amazing, along with the pistachio and cinnamon – loved them all), and finally Veselka for some pierogies.
From there, we headed up to see Just in Time, which we all loved – such a FUN show about the life of Bobby Darin. My dad listened to him when I was growing up so I was familiar with all the music, which was great fun. The theatre is intimate and the performers move around quite a bit so it’s engaging and fun. Sadly, Jonathan Groff, the headliner who is incredible (he played King George in the original Hamilton and is the voice of Kristoff in the Frozen movie), was off for literally the exat days we were there, so we missed seeing him. But the understudy still did a great job and the others were phenomenal! We had a great time. Joe’s Pizza was right on our walk home from the theatre, so Dan and I stopped for a slice because the line was surprisingly not huge when we arrived – it was delish! We’d never had it before but definitely a very classic New York slice. The line was twice as long when we got out, so if you go after a show, try to get over there quickly.
The next morning, we headed out bright and early for a terrific pay-what-you-wish walking tour. The one we chose started in Lower Manhattan near the Town Hall building, where we learned a bit about the history of the city. From there, we walked over the Brooklyn Bridge and learned about its construction, looked back toward Manhattan, and about the people who helped bring it to fruition. Finally, we ended with walking around Brooklyn Heights and DUMBO, learning about its people (including some who were instrumental in the Underground Railroad), history, and culture. Our tour guide, John, was terrific – very knowledgeable but also super engaging and fun. We all loved learning so much about the city and taking some photos of the beautiful views we saw!
Our tour ended right near Juliana’s Pizza, so we stopped in there for lunch, which is always a solid choice. From there, we headed to the Brooklyn Museum, which none of us had ever visited before. We loved it! A terrific collection, and we especially loved the feminist art installation, The Dinner Party by Judy Chicago. In it, she set up a massive triangular table with 39 giant place settings to honor 39 amazing women, with the names of 999 others written on the base of the table. It was special seeing those who were included and thinking of other amazing women in our lives.
After the museum, we headed back to our hotels to change for our other main event for the week – Masquerade! I’d been looking forward to this ever since I had several friends attend and absolutely rave about it. It’s basically an immersive Phantom of the Opera experience, and it is spectacular. The performers sing so close to you and you move through the whole experience. I don’t want to spoil any surprises for anyone who may attend, but just know that it is absolutely worthwhile and one of the most amazing theatre experiences I’ve ever had. For the event, people are encouraged to dress up (only black/white/silver allowed) – I wore this dress and purchased this set of 2 really fun and affordable masks for Dan and me to wear.
After, we grabbed some food at Lolita (for all of London’s terrific food, it’s a bit lacking in Mexican), which was close and pretty good food. Not one I’d venture out of my way for, but a good option if you’re in the area. Then back to the hotel to sleep!
On our final morning, we got up and had a pretty leisurely breakfast at our hotel before finishing most of our packing up. Then we headed over to The Frick Collection, a wonderful art gallery that was recently renovated. I visited once briefly years ago, so was excited to come back and explore more. We also got to meet my wonderful friend Jessica there, who happened to be in town with one of her friends. It was so lovely to see them and to explore the museum together. There were several impressive rococo & Impressionst works, along with an amazing new permanent installation called Four Seasons by Flora Yukhnovich. We almost missed this room and I’m so glad we circled back to it – it was stunning! Gorgeous giant florals covering every wall; pretty much I want exactly that in my house, haha.
After the Frick, we were planning to pop into Trader Joe’s to get some snacks for our kids, but it was snowing quite heavily at this point and it was absolutely beautiful. So we couldn’t resist a stroll through Central Park! It was so beautiful and a wonderful capstone to the trip. Our couple friends and we then headed over to our hotel to get our luggage out of the room and eat some of our leftovers we’d accumulated and popped into our room fridge (the breakfast area had a microwave, which was perfect).
After lunch, we all walked over to see The Outsiders, a musical I’ve been excited to see for years! On the way, we stopped into Angelina of Paris to get hot chocolate – my girlfriend had joined me on my Paris girls’ trip, but her husband and Dan had never had it, so we figured the snowy weather demanded it. It was delish, of course. Then The Outsiders was phenomenal – beautiful and moving and the music was amazing. So glad we got to see it.
After that, we stopped into John’s to grab a pizza to share. (It was good! Not mind-blowing, but very good and also convenient.) Then we walked back to grab our luggage and change into comfier travel clothes, and headed over to the airport. On the way, we stopped at Trader Joe’s to quickly grab some snacks since we hadn’t before, then got over to JFK. The ride was quick and we fortunately had plenty of time to even visit the Chase Sapphire Reserve lounge, which was lovely and even had showers. It was so nice to be showered and fresh before hopping on an overnight flight – without even needing to manage kiddos! Dan and I both slept so well using this airplane sleep pillow and this amazing travel blanket that buttons in the back so it doesn’t slip down. (Discount code PASSPORT for the blanket)
There are always SO many things to do in New York for couples and anyone else, and it never feels like enough time! But we loved going back, seeing a few shows, and visiting a few gems that we either hadn’t visited before or hadn’t for a long while, and all with wonderful friends. It was such a wonderful New York couples getaway!
Have you visited New York before? I’d love to hear some of your favorites!
