I’ve said it before, and I’ll say it again: one of the things we’ve loved most about points and miles is that it helps us save significant money on trips we would have typically paid cash for to begin with. So, it’s not just about the dream trips to Hawaii and Europe, it’s also the trips to visit family, the college visit trips, the kid’s sports tournaments, and on and on. We recently took a trip that checked the boxes of being both a family trip and a super fun, exciting adventure: New York City. The Big Apple.
We have visited NYC in the past, and typically have driven and done our best to find the most affordable Manhattan hotel we can. We love NY and our family, so this has been worth the long drive, stressful Manhattan parking adventure, and pricey hotel cash rates. This time around, though, of course we were gonna use points and miles for flights and hotels. Sometime over the summer, Tom declared that we would not drive to NYC this time, and he would like to fly if we could make that happen with points. Fortunately, you can book United Saver Awards via Aeorplan (Air Canada’s reward program), and there are 5-6 flights a day between PIT and Newark. As a side-note, getting to know the Aeroplan program is useful out of PIT – you can book nonstop United Flights to NYC, San Francisco, Chicago, Denver, and DC. This can be useful for routing and repositioning, or just for when you want to go to those places. You also can transfer 4 out of the 5 major transferable credit card points to the program, whereas United itself only participates with Chase. We happened to transfer some of our Chase Ultimate Rewards during a transfer bonus to Aeroplan and got each of our round trip tickets for 10,000 points plus $35. For reference, the Saver Award on United is 18,400 points round-trip for this flight, and the cash price was right around $250. That’s a little over 2 cents per point value, which we’ll take for a domestic flight. Even with paying the fees per ticket and the NJ Transit train fare from the airport to Penn Station (very easy and cheaper than Uber!), we think we came out ahead by being free of gas, tolls, insane parking fees, and frustration.
Like anything in New York, the options for where to stay are limitless. We typically stay in Manhattan in Midtown for its convenience to all the things the kids want to do, plus it isn’t far from where our family lives in Queens. For better points prices, you can move down the island a bit and choose something like the Hyatt Place in Chelsea (Category 5; 20,000 points standard), or if you aren’t opposed to using a little bit more public transportation and seeing beautiful sunset views of Manhattan from across the river, you could try the Hyatt House Jersey City or Hyatt Regency Jersey City (both Category 4; 15,000 points standard or bookable with a Cat 1-4 free night certificate).
It’s funny I’m mentioning all of these Hyatt properties… because we actually stayed at the Hilton Times Square this time. Earlier in the year, Tom and I both took advantage of a sweet deal to open the Hilton Honors Business card. When we did this, Tom got 9x on groceries for three months on his Amex Gold, plus 10,000 referral points. Amex is unique in that you can refer from most of their cards to any other personal or business card. After I opened the Hilton card, I then referred him to the very same deal. The deal itself was for a free night certificate plus 150,000 Hilton Honors points once the spend was completed. This hotel was 90,000 points per night and together we booked 2 rooms for 3 nights using our free night certificate, the points from the sign-up bonus, plus some existing Hilton points I already had. Hilton Honors makes it really easy to transfer points between people, so I gave Tom what he needed to complete his booking, and we were good to go. We are newer to the Hilton program, so discovering this was a very pleasant surprise – not all hotel programs make this easy.
As Hilton Honors Biz credit card holders, we were granted immediate “Gold” status in their loyalty program. This gave us each a $36 food and beverage credit to use at the bar or café each day of our stay. This sounds good, but in actuality was about enough to cover 4 coffees for me, Tom, and his parents, a breakfast sandwich for the favorite child of the day, and 2 muffins for the runners-up. This is to say, the price of food at the hotel was pretty high, as one comes to expect in Manhattan. That’s ok though, because we had a full itinerary of places to go and brunches to try. Other than the pricey food, this hotel was quite nice. I was worried it would be loud being just off Times Square, but the rooms were quiet, the queen beds (hard to find in all NYC hotels) were comfortable, the rooms were clean and spacious, and the hotel staff were kind and helpful. We were able to check in early so we got to a room and were able to drop off our stuff – this was a plus for the hotel. With the Gold status we could have also gotten late check-out, but we didn’t need this.
If you throw a rock in NYC, I imagine you would find something interesting to see and something delicious to eat. From here, I’ll just give the deets on the rocks we threw and what we did and ate. Take it for what its worth!
We started our trip with visiting family in Queens – and after finally getting there after someone boldly led us onto a train going Brooklyn-bound (it was me), we had quite possibly my favorite lunch ever at a little Greek restaurant in Astoria, NY. Tom’s brother described the décor of this restaurant as “like eating in the Bernstein Bear’s treehouse,” which is what sold us. And it was accurate. But more than that, the food was delicious. We had a whipped feta dip to start, and I got the best stuffed tomato of my life, while Sam is sure he had the best T-bone steak of his. If you ever find yourself in Astoria, NY, you will not be sad if you have a meal at Agnanti. Later that evening, after taking the correct train (the only train) back into Manhattan, we met up with Tom’s parents who arrived after us, and had dinner at the historic Birdland jazz club. Our kids are all musicians, so this was a really fun addition to our trip. The food there is just ok, but that’s not why we went! We got to see Lakecia Benjamin who was so cool, and had just found out she was nominated for a Grammy.
We started out our Saturday with brunch at Ellen’s Stardust Cafe which was really fun. It’s the singing waiter cafe. We wandered around Rockefeller Plaza, saw them starting to put up the tree, went into all the stores, then headed down to the Tenement Museum. This is something I’d been wanting to do, and I highly recommend going if you ever spend time in New York. They guide you through an old tenement building on the Lower East Side and share the stories of several real families. This was a true highlight of the trip for me. But everything felt like a highlight. For instance, our next move was an amazing dinner in Little Italy after walking through Chinatown.
The crown jewel of the day for my kids was seeing Sweeney Todd on Broadway. Their school is putting on their own production this year, and they are playing in the pit. We saw Josh Groban play Sweeney, and it was just amazing. I really didn’t think I’d like a show about a demon barber, but turns out I have a dark side too! Our last full day was more relaxed, with brunch and strolling through Central Park and around the Met, and then checking out the holiday stalls at Bryant Park. We ended the day at a family favorite – Japanese barbecue. Turns out we like paying to cook our own food over a tiny grill at the table.
This trip was one for the books! I think early November is my favorite time to visit NYC. The holiday crowds haven’t started swarming yet, but there are glimmers of Christmas spirit starting to pop up here and there. Plus, the weather is typically mild, and there are still colorful leaves throughout Central Park. I loved the ways we used points and miles to make this trip happen – it freed up the budget to do more of the fun things everyone wanted to do. Can’t wait til our next trip back!
