Travel Planning: New York City at Thanksgiving

So many flags, so little time… (source: Google Maps)

2018 has been quite the travel year for me! Normally, Mr. P² and I do maybe one long-distance trip and one road trip per year. Between our trip to Paris last December (yes I’m including that in this roundup), a last-minute trip back east, our road trip to San Diego Comic-Con and an upcoming overnight to Lake Arrowhead, I’m all over the place! However, the biggest trip this year as far as I’m concerned is my very first trip to… New York City!


People who know me are always shocked when I tell them I’ve never been to New York. It seems like one of those places that most casual US-based travelers have checked off their list pretty early on – like Hollywood, Vegas or Cabo (haven’t been there either). For some reason, New York has never seemed like a priority and always plays second fiddle to other locations for me (hello, Paris!).

That all changed this year when my mom decided she was going to check off a bucket list item for herself – being in New York City at Thanksgiving, and experiencing everything that entails. I previously mentioned that I’ve been getting into travel hacking, and when she told me last winter she was going this year, I used my recently acquired United MileagePlus rewards from the Chase United Explorer Card sign-up bonus to book a round-trip ticket. All in, it cost me 55,000 points and $12 in taxes and fees versus paying almost $700 for the same ticket.

If you’re wondering how that could have possibly been enough points to cover both Mr. P² and myself, wonder no more – they aren’t enough! Although Mr. P² would love to be joining us, the only reason I can go is because my mom is paying for the hotels, and I had the points. That’s the difficulty with travel hacking as a couple – if one half has the card or the points for a flight and the other doesn’t, there’s always an imbalance. However, he graciously offered to watch the pups while we’re gone, which thrills my mom because it’s one less thing she has to worry about.


I’ve always heard stories from friends and family about how busy New York City can be during the holidays, and especially Thanksgiving. As a planner and fairly seasoned traveler, I do everything in my power to avoid travelling on or around Thanksgiving and other major holidays, so the irony of travelling to New York specifically to immerse ourselves in the holiday insanity is not lost on me.

Keeping this in mind, I’ve been trying to find a balance between the crazy of the holiday and actually experience New York City. I will add a caveat that we only have a few days, so I won’t get a chance to visit the other boroughs outside of Manhattan. Yes, I know this is an inhumane crime against every New Yorker, but sometimes these things can’t be helped. Next time, I promise!

As always, I’ve been researching like crazy. Since we’re trying to squeeze in three shows, the parade, AND the major touristy stuff in 4.5 days, the goal is to strategically combine different activities to maximize our time. We already have our tickets for Frozen, the Radio City Music Hall Christmas Spectacular and the New York City Ballet’s Nutcracker. I’m a musical theater kid at heart, and with this being my first time experiencing Broadway, you better believe I’m squeezing in as much as possible (read: what I can afford).

The Macy’s Thanksgiving Day Parade is the one thing that, as a planner, I find daunting. Between getting up at an unholy hour in weather this California girl is probably wholly unprepared for and dealing with the crowds to find a good spot to watch, I’m worried we won’t have an optimal experience. I’ve read several different blogs about the best places to watch the parade from the street, what time we need to get there, and areas to avoid, and it seems to be a roll of the dice. Right now, our plan is to head to the mid-60’s and Central Park West to try our luck there, but if you have a better suggestion, please let me know!


I hate to admit it, but sometimes embracing the “tourist” aspect of travel can be really fun. It justifies doing the sillier things that locals swear they’d never do (but secretly want to), like the Big Bus tours. With most of our holiday activities happening near our hotel, I wanted to take a convenient Hop-On Hop-Off tour to check out some spots in lower Manhattan. From what I can tell after flagging a few dozen stores, historical sites & yums, there’s a bus route that runs right through the heart of these places, and will be perfect for seeing the sites and fulfilling my shopping fix!

The other touristy thing we’ve got planned that every blog says not to do is a tour to the Statue of Liberty and Ellis Island. I know the Staten Island ferry goes right by it and is free, but as one of the landmark monuments of our country, I really want to see her up close and go to the top if it’s open. One of the things I love doing as a traveler is climbing the stairs or taking the elevator to the top of tall public spaces, and I’ve got a pretty good repertoire – among others, St. Peter’s Cathedral, the Duomo in Florence, the Eiffel Tower, and the scariest of all, the Leaning Tower of Pisa.

Other noteworthy locations that I’m still considering are the Empire State Building, the 9/11 Memorial Museum and Top of the Rock. We may only be able to squeeze one of these in due to our already busy schedule, so if you have a preference, drop a comment below!


If there’s been one recurring theme throughout my research for this trip, it’s that New York has some of the most diverse and unique culinary offerings in the world. Every blogger agrees that not eating at these magical meccas of mouthwatering temptation should be considered a foodie sin.

Keeping that in mind, I’ve been using my old friends Yelp, Google and Pinterest to find places that are a.) yummy, b.) affordable and c.) convenient. And before anyone gets pissy, I know Yelp is shady and their algorithms aren’t fair or impartial to small business owners who can’t afford to pay for their reviews. It’s ultimately nothing more than a starting point for me and, as all researchers will tell you, having more than one source of information yields better results. Many born and bred New Yorkers have great and resourceful blogs full of tips and tricks for tackling their beloved city. After all, if you can’t talk to a local in person before your trip, read their blog!

I will admit, some of the restaurants, bars and other places I’ve flagged are incredibly popular and utterly Instagram-worthy. As with our trip to Comic-Con, I fully anticipate lines in some of these places, and I’ve come to accept that if it means getting edible cookie dough or fist-sized chocolate chip cookies.


I’m currently experiencing my least favorite part of travel – the holding pattern. I’ve researched up the wazoo, made reservations galore, have show tickets in hand, and… we don’t leave for another month. Travelling without Mr. P² is hard and I know he would love to visit New York at some point, and we will, but for now I’ll enjoy a Gilmore Girls-style mom and daughter visit to the Big Apple.

All the best,

Mrs. P²

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