New York City in 3 Days: Itinerary & packing for frequent or infrequent travelers

Are you a frequent or infrequent traveler? It’s choose your own adventure time! If you want to run and skip ahead to a 3 Day New York City Itinerary (this is part 1 of 4 posts) scroll down to below. If you’re like me, and want to more casually take in the scenery at a strolling, walking pace, just start reading here:

I’m an infrequent traveler. The last and only other time I visited New York City was when my family took a cruise with my Grandparents to Bermuda in 1999. We only passed through with just enough time to board our ship. I didn’t get to see the city that go-around except a quick glance at the Statue of Liberty as we pulled away. There is a picture of me with the Twin Towers in the background somewhere, but I couldn’t find it. (I’ll add it here later if I locate that)

I was with my sister Jenny on September 11, 2001. We shared a meal in Dinkytown near the University of Minnesota’s Minneapolis campus where I was studying music, theatre and dance. She was doing one of her practicum residencies studying at a nearby hospital. We met up that evening still in shock at the day’s events unfolding.

I recently spent 3 days in New York City with her. Just to be clear, we had part of a day on either end for travel. Flying Madison, Wisconsin to Chicago, Illinois first… and then to Newark, New Jersey. We took an Uber across to the island of Manhattan. Then we reversed our travels back at the end of our trip. It was a Tuesday to a Saturday, so Wednesday through Friday were the days we had to see New York City.

I hadn’t flown in 14 years. I know. The last time I flew was to Orlando, Florida in 2011 to experience Disney World with my 5 year old twin nephews. Before that I’d flown at least semi-often (Seattle, Mexico, Arizona, Florida, Europe, to name a few) Last year when we went to Orlando we drove! That was long. Not a whole lot has changed as far as air travel goes, except of course TSA (Transportation Security Administration) is a bit more robust now, and checking in is now all done by cellphones. Kiosks are for self-service things like bag tags, which we used on our way back. (Not a fan of those) I did get a printed boarding pass on the way out of Madison, maybe only because there was practically nobody in the airport. But that seemed like a novelty. I had walked up to the United Airlines counter and then realized my sister had already remotely checked us in. She hadn’t arrived yet though, and the three people behind the counter looked like they had nothing to do. The guy might have printed me a boarding pass catching on that I was not a frequent traveler. He probably thought I might like a paper ticket in hand. I did. I was happy to get pointed in the direction of security check in next, which went pretty smoothly.

After I put my things into the bins I stepped into a 360 degree scanning pod and was asked to stand with both arms up in the air. I needed to look forward as I was assessed head to toe like getting a full body x-ray. That was different from a decade ago.

I used an old soft-sided Samsonite suitcase. (later I found out the wheels were way better than my sister’s newer rolling hard-sided suitcase. You can see a corner of that below) I had a first aid kit with my medicines in it in case I needed an extra bag on the side that TSA would let me carry through. I probably wouldn’t do that again, but here’s how my luggage looked:

Bringing an empty water bottle to fill once past TSA worked great! My sister, who is a frequent traveler, suggested using a clip to attach it to my bag. That was handy. I also brought another empty plastic water bottle to fill up.

I had stressed a bit about my clear, quart-sized bag of 3oz or less liquids. We knew in advance we were not going to check a bag so I was allowed one quart-sized bag. I soon discovered it was really hard to fit everything I wanted to bring in that. But I ran to Walgreens the day before and got a TSA approved clear zipper bag, and some cute little silicone containers (all pictured below) I used for things like face lotion and Vaseline. I also grabbed a travel-sized shaving cream and tiny deodorant, as well as a small sunblock stick. Everything fit great!

TSA approved travel containers

Okay, so I’ll skip going into detail about all the running to the connection flight stuff because we sat on the runway forever in Chicago. We got to our terminal just as they were reaching our boarding group. I will say my sister’s app that she was using said it was a 15 minute walk to our terminal, but we had to run it in at least half of that to make it in time. I also quickly realized her walk is equal to my run.

I’ll also skip quickly past the part about my first experience in an Uber driving from the airport to New York City. “Welcome to the future,” our driver said as I couldn’t find the door handle to get out of his Tesla. I eventually pushed the button to exit. Was this our hotel? I tapped my left pocket with my new cute ivory colored wristlet in it. It was there. I got it from Target and used it to hold my license, a bit of cash for tips, and one credit card. It was there. But where was my cellphone? It wasn’t in my right pocket. I checked my new Vera Bradley backpack. It was in the front pocket. Whew. I decided in that moment I needed to be consistent and put it in my outfit pocket every time. Tapping my right side, tapping my left side… Okay, I was set. I love pockets!

Before we left I had ordered some RFID protective sleeves to keep my credit card chip secure. I gave my sister some as well. I’ll have to admit this was an impulse buy. My Dad had just texted my sister and I about our plans for safety during our travels. I wasn’t a bit worried, but down a little rabbit hole I went, and those landed in my Amazon cart. I sent a link to my pops. Smart Annie, I’ve got this, I thought.

Wristlet with RFID sleeves and Backpack

The city that never sleeps
We rolled our luggage up to the other side of the street where our hotel’s entrance was. My sister had told the hotel we’d be in late. It was probably 11:00 or 11:30pm, or was it 12:00 or 12:30am? Whatever it was it was an hour ahead of our time back home. I was tired, but wired too. Time began to feel irrelevant starting about here anyway. I texted my husband letting him know we arrived. Would he still be up? The lobby had a store with designer dresses and handbags I could see through a window. It reminded me of the movie Pretty Woman.

We stayed at The Residences, a Hilton Club on the 44th floor! Our ears popped on the way up the elevator. It was a great room, included a main area with pullout couch (I slept on this the second and third night), a mini-fridge, armoire my sister used to hang her outfits, TV, table and chairs, Keurig and bottles of water. No microwave though. The other space had the bed and bathroom and a lower dresser I immediately claimed for setting my backpack on and unloading. A closet in that area had two white fluffy robes, one of which I wore a couple of times.

I looked out the window and downward to the steady flow of yellow cabs in the busy street below. It was so so high! I was reminded that my sister is a bit afraid of heights when she stayed back. She wanted me to close the curtains and come check out the shower, which was amazing! It was one of those with multiple sprayers coming out at different angles and a waterfall coming down from up top, super spacious. The toilet had a heated seat! I never tried the toilet features she said Tokyo has everywhere. She’d ran a marathon there last year. This could be a side note, but actually is super important for me to mention because it influenced our pace for the trip.

I traveled with a marathon runner, an olympian level athlete. No kidding. She’s done the Boston, NYC, Chicago, Berlin, London, and Tokyo marathons. I hope I didn’t forget one of the world ones. Oh, and for fun she did the Patagonia marathon in Chili last year. My niece, who we were there to see dance in New York had gone along on that trip. Next she’ll do one in Cape Town, Africa later this fall. She’s done other ones too, like the first one she ever did was the Minneapolis City Marathon when I still lived in the Twin Cities area. She’s really fit, a frequent traveler like I mentioned, and a firecracker known as my sister. She mentioned wanting to check out the workout room in the morning while she was making herself tea. She grabbed her book and was slipping on some readers before I could even think about what to do next at the moment. I grabbed my TSA approved containers, and got to it.

A couple of photos from our hotel room are below.

3 Day New York City Itinerary: (The links below are coming soon. Posts will include more details about each stop on our adventure, as well as where and what we ate when, and what shows we saw.)

New York City Day 1
Rockefeller Center & Radio City Music Hall
FAO Schwarz Store
Central Park
The Plaza Hotel
MOMA (Museum Of Modern Art)
Time Square
Grand Central Terminal
Dinner Reservation #1
Broadway Musical #1

New York City Day 2
New York Subway
Statue of Liberty & BMW Bridges
Wall Street, New York Sock Exchange & Girl with Bull
Tiffany’s
Trinity Church & Cemetery
911 Memorial & Survivor Tree
Greenwich Village
Dinner reservation #2
Broadway Musical #2

New York City Day 3
Chelsea Market
The High Line (planned to see but ran out of time)
Dance Show (Broadway, Upper West Side)
Bryant Park, Public Library, Empire State Building (walked by only)
Holland Tunnel

Have you been to New York City? What was your adventure like? If you haven’t, what would be your top thing to see? Leave a comment below.