When I was growing up, my dad came to work in New York regularly to meet clients and visit the World Trade Center. Several times a year, he would turn it into a family vacation, and some of my favorite core memories are of clawing our way to the counter at a 1980s muffin shop, standing in the TKTS line in subzero temperatures, and scouring the countless shops on Orchard for the seamstress shop that produced Sherif bags.
One time, my mom got pickpocketed in Times Square, and we had to walk all the way across town to borrow money from my dad’s partner to pay for a cab to Greenwich Village. Another time, my dad got accosted by a bag lady for issuing a chipper “Good morning!” when she was in no mood for it. It was literally adventure after adventure. And my mom could not get enough of it.
She lived in New York from maybe 1963 to 1967, trying to make it on Broadway. While that never manifested, she had incredible experiences. She was in tons of shows and sang in mafioso nightclubs. The City became part of her identity, and through our many escapades around Manhattan, she made it part of mine, too.
We’ve brought Josephine to New York a few times in the past but never during the holiday season when New York shines the brightest – at least, not when she was old enough to remember. I’ve wanted to, but I just haven’t made the time. However, this year, I learned that Chess was playing on Broadway, and I immediately knew the time had come.
My mom and I saw Chess in Houston (I think we saw it several times) and then followed the production to see it again in New York. We had the soundtrack and sang the music constantly. The show itself became woven into our bond. And I knew that if it were playing on Broadway and she were alive, she’d waste no time in buying tickets and planning a trip to see it – even if she were mid chemo or directly post-op. I couldn’t let her down by missing this opportunity.
So we booked the entire trip about 8 days ahead of time, with just a few key activities besides Chess on the agenda:
1. Buy a Fornasetti plate at Bergdorf’s
2. Visit the Morgan Library
3. See the light show at Saks
4. Gawk at Christmas window setups
5. Dinner at Scalinatella
For everything else, we played it by ear, teaching Josephine that the beauty of Manhattan isn’t in planned activities but in spontaneity.
So here’s how it all played out:
Friday –
– Flight at 10:15, arriving at LaGuardia at 2:45PM. This felt a little early for the morning after Thanksgiving shenanigans, but we pulled it together, and I’m so glad we did! We were in our hotel room by 4:30 and eating hot dogs and pretzels by 5:00.
– We immediately walked out to see the hubbub of Fifth Avenue. We didn’t go into any stores; we just experienced the bustle of the street itself, including the exciting, sparkly windows at Bergdorf Goodman and the bright, musical extravaganza of the Saks storefront show. I remember seeing that for the first time with my parents about 7 years ago. Josephine was with us, but she was too small to appreciate it. My mom was a sucker for anything glitzy, and she was simply mesmerized by the spectacle. I could feel her with me this time, encouraging me to be just a little more wondrous and to encourage Josephine’s joy. It was wonderful.
– We were a little disappointed to learn that Rockefeller Center would not turn on the tree until December 3, but we did get to see the ice skating rink and promised ourselves we’d see the tree next year.
– We took Josephine to St. Patrick’s Cathedral, my mom’s favorite church in the city. Josephine did what my mom always did: she promptly bought a candle and lit it in front of the Virgin Mary. I know she said a prayer for my mom. Damn, we all miss her.
– Before we knew it, we were hurrying back to the hotel to change clothes for dinner at Scalinatella, one of my family’s favorite restaurants in the city. My mom and I happened upon Scalinatella one late night in the 90s. It was pouring rain at perhaps 9:30PM, and we couldn’t get a cab. We were starving, but we had no idea where to eat near 61st and 3rd; we were way outside our normal radius, and of course this was way before Google Maps or Yelp or Eater. So when we saw glass windows lined with wine bottles and felt a decidedly Italian vibe, we took a chance, opened the door, and descended a small staircase (a scalinatella, if you will) into the tiny dining room below. The restaurant was well into last call, and they could only make one thing: spaghetti al pomodoro, tossed tableside. It was one of the best meals I’ve ever had in my life, and we’ve been repeat customers ever since. But this was my first time to take Josephine, so I was way more excited than usual.
Fortunately, Scalinatella has never sacrificed the food and ambience that made our first night there so special. We sat amid Manhattanites, not a tourist to be seen, and we thought the guy at the table next to us was Aaron Sorkin, but we’ll never know. We ordered a ton of wonderful things, including zucchini blossoms stuffed with burrata and prosciutto, grilled baby octopus, spaghetti al pomodoro (of course), fettucine bolognese, snapper Livornese, grilled lamb chops, and a salad (you need your greens, you know!). True to form, Josephine tried it all, loved it, and walked home like a champ in the cold. See you next time, Scalinatella!
– We wrapped up the night with chocolate cake in the room. Josephine and Jamil watched Ace Ventura: Pet Detective while I sawed logs.
– What a full, wonderful first six hours in the city!

















Saturday –
– We slept in a bit and let Josephine get a bagel and lox in the room. Then, we declared that it was time to scamp (that’s Jamil’s term for wandering around and just happening upon cool things to see and do).
– We walked down to the Morgan Library, founded by the descendants of J.P. Morgan to showcase the phenomenal acquisitions of that legendary banking tycoon. Morgan was an avid collector of all kinds of historical items, from ancient objects like tiny, cylindrical carvings, used to seal documents in Assyrian and Babylonian societies, to the Gutenberg Bible. We spent about an hour in the library, and we got lucky enough to crash a docent’s presentation about the library’s literary collection. The next time we go, I’ll make sure we join one of those tours. I cannot wait to go back.
– From there, we meandered over to the heavily Asian area around Broadway and 39th to look for Korean skincare products. Along the way, we stopped for (subpar) ramen at Nishida and got Josephine a (fabulous) matcha parfait at Nana’s. Then, we took Josephine to Macy’s, just so she could see the madness of that New York institution during the holidays. It was indeed crazy.
– Then, we started our trek back to the hotel to get ready for the event that prompted our trip in the first place, Chess at 7:30PM. Josephine is such a good sport about walking on our trips. She puts in thousands of steps a day and rarely complains. It’s amazing to have brought a true companion into this world.
– Chess was good. The performers had incredible voices, and the music was great. However, someone played Frankenstein with the storyline, and it’s just too contrived. It already required the suspension of disbelief, but this went too far. I won’t see it again. But Josephine was a great sport, as usual – always happy to see a musical. Really, any musical.
– We closed out the night at Avra Estiatorio off Madison and 61st. We’ve been there for late-night dining before, and it’s a great post-theatre option. The Greek cuisine is pretty authentic and mostly good. The grilled halloumi is great, served with honey and citrus. The grilled calamari are the best around; it’s thick, well-seasoned, and not too chewy. The hummus leaves a little to be desired. It’s pretty flavorless. But then again, a lot of hummus rests too heavily on the chickpeas for flavor, when they’re bland as all get-out. Sadly, we had to do this dinner without Josephine, for the most part. She drank part of a mocktail, ate a piece of pita, and then put her head in my lap to snooze until the check came. But that was also pretty sweet and nostalgic. I love her so much.



















Sunday –
– This was really my shopping day to buy a crazy Fornasetti piece to put in the corner of my kitchen. The best selection I’ve seen is on the top floor at Bergdorf’s, so that was at the top of the agenda. Josephine was appalled by the surrealistic imagery that put Fornasetti on the map. She begged us not to buy the clock that ultimately called our name, but Jamil and I reminded her that our home is filled with “weird” art. It’s what we love. Eventually, she’ll love it, too!
– As much as she disliked the Fornasetti, she was obsessed with the Christmas decorations that filled the whole store, especially the top floor, where there were all kinds of crazy Christmas trees and ornaments and gigantic peacocks. We let her pick out some ornaments for the tree at home, and we gawked at the ridiculously expensive Christmas trees made out of antique brooches, watch faces, and bracelets. It was so fun.
– Finally, it was time to have lunch and head to the airport. We stopped into La Goulue, a French bistro right next to our hotel. Jamil had French onion soup with a Caesar salad, while Josephine got the potato and leek velouté with a butter lettuce and chive salad. We all split the mussels, which were so fresh and delicious, I could have eaten the entire order myself.
– And before we knew it, we were in a Blacklane car on the way to catch our plane, fighting traffic and arguing with police officers who were blocking the way to Terminal A at Newark. It was chaos, and Jamil hopped out to print the luggage tags before the window to check bags closed. But we slid through security with Clear and made it to the gate with time to spare. I love that kind of chaos.
This trip was so amazing that all three of us want to make this a regular affair. We’ll see if we can pull it off. But I came to New York several times a year when I was Josephine’s age. I’d love to give her that same opportunity. Now, granted, I didn’t go to Europe and Asia and Florida and you-name-it, like she does. And there’s only so much time in a year. But as her schedule gets tighter because of activities and academics, maybe we’ll find ourselves in Manhattan more than other places. Who knows, but I’m looking forward to it.








