With the 3-day weekend this October, our family decided to trek down to New York City.

Broadway plays have just re-opened (Fall of 2021), so we wanted to catch a show. In addition, we wanted to see a few museums we hadn’t all been to before (we ended up choosing the 9-11 Museum and the NY Transit Museum), and see some old favorites (e.g. Brooklyn Bridge, Central Park). We also did a harbor cruise, and overall filled the weekend with some great food and a lot of walking!

Friday Evening Arrival

Living in Greater Boston, we decided to drive to NYC. It’s often about a 4 hour drive – our record time is about 3.5 hours; it’s [usually] hard to beat that by flying. We left late afternoon (4pm) on Friday, trying to dodge both some Boston traffic and NY traffic, though the holiday weekend traffic made that trickier. Instead of arriving around 8pm, we got to the hotel a bit after 9:30pm.

Recently, we’ve been using the Spot Hero app to find parking (no sponsorship, we just like it); we did this in DC last summer, and in NYC this month. In this case, we paid about half the hotel’s garage rate, and had to walk about ~5 minutes to our hotel. Be aware that in NYC, nearly all parking garages require using valets, to pack more cars in the garages. Not awesome with Covid, but there aren’t a lot of choices.

The boys decided that they really wanted to take an evening walk to Times Square, so the 3 of them headed out while I got all of our stuff organized.

We were happy with the location of Marriott’s Residence Inn Manhattan Midtown East, walkable to many Midtown locations, and close to Grand Central with its express subway trains. When booking rooms in NYC, we find that we need to look more carefully at bed size than in other places, since many of the rooms we saw had beds that are just double-sized rather than queen-sized. This hotel fit the bill!

Day 1: 9/11 Memorial & Museum plus a Harbor Cruise

On Saturday morning, we got breakfast in the hotel, then headed towards Grand Central Station to catch the subway to Wall Street.

9/11 Memorial & Museum

From there, we walked to the 9/11 Memorial & Museum located near the One World Trade Center, enjoying the street art on the way.

When we visited New York City in 2016, we had considered visiting this museum, but in the end decided that our boys were too young to have the images they would see implanted in their brains. Now that it is five years later, our boys are plenty old enough to get the full picture of the events of 9/11.

While Jeremy and I lived through the news coverage of 9/11, our teenage boys had only heard the stories. Through a series of videos, timelines, and artifacts, the museum does an excellent job of conveying the horror of this day, the senseless violence that ensued, and the bravery of many people that pulled together to make the best of the situation.

If you are ever in NYC, particularly if you take a family trip and are traveling with teens, or if you simply want to learn more about what happened on 9/11, make sure you visit this museum. Just keep in mind that a lot of the videos are not appropriate for young children.

Lunch in Little Italy

For lunch, we were debating between Little Italy and Chinatown, but in the end Little Italy won out. This time we did looked at reviews in advance, rather than just walking into a random place, and we made our way to Rubirosa Ristorante.

Delicious! We got the last table and by the time we left people were being told that there was a two hour wait.

But Chinatown would have made a fantastic lunch too!

A Long Walk

From Little Italy, we doubled back into Chinatown, then continued to Soho, NYU, Greenwich Village, and then made our way to the Chelsea Pier.

While walking by NYU, we decided to sit inWashington Park for a bit and enjoy some of the musical street performers.

A Harbor Cruise

We had a 4:15pm reservation on Classic Harbor Cruise’s Statue & Skyline Sightseeing Cruise, so we kept a close eye on our watches to make sure that we would arrive at the Chelsea Pier at the right time.

If you have the opportunity, we would highly recommend this 1.5 hour cruise. They limited the guests to the number of tables, each group was separated by a plastic divider, and there was plenty of room for each guest to enjoy both the indoor and outdoor areas of the ship. It definitely wasn’t one of the largest boats on the harbor (part of the draw; intended to be a more intimate environment), and we could feel the waves, but overall the experience was quite pleasant.

We got some amazing views of the city, the Statue of Liberty, and Ellis Island, but if a cruise does not fit into your budget, consider either taking a larger ship or taking the (free) Staten Island Ferry instead. The ferry won’t take you quite as close to the Statue of Liberty, but it works as a way to get a view of this amazing piece of history.

The High Line

For dinner, we considered stopping at the Chelsea Market, but in the end opted for street food located near this slightly odd sheep display. Yum!

Afterwards we took a walk on the High Line elevated walkway from Gansevoort Street to the Vessel. The views of the city were amazing!

The Walk Back

I was feeling tired, so I hopped on the subway stop near the Vessel and walked back to our hotel from Grand Central Station. While going through one of the subway tunnels, I encountered a man playing lovely music on an accordion.

The boys decided that they wanted to walk all the way back, making sure to go through Times Square again. The amazing Lego store displays at Rockefeller Center are always a hit!

Day 2: New York Transit Museum plus a Broadway Play

New York Transit Museum

Since the boys were up a bit later than usual, we got a somewhat late start, but managed to make it to the New York Transit Museum when it opened at 11:00am. Note that advance tickets are currently required (here and most NYC museums in 2021).

Built inside an unused subway station, this is an amazing museum that features the history of the New York subway system.

In addition to lots of helpful exhibits showing the construction of the subway system, timelines of the history, and various artifacts, the real highlight was the collection of old trains that are lined up along the train platform.

While it was fun to see how the trains have changed over the years, both on the exterior and interior, what really stood out for us were the ads. Today’s ads are really quite boring in comparison to the ads displayed in the museum’s subway cars.

DUMBO Neighborhood

When we left the museum in downtown Brooklyn, there was some slight drizzle, but we decided to do the 15 minute walk towards the Brooklyn Bridge and the nearby DUMBO (“Down Under The manhattan Bridge Overpass”) neighborhood as intended.

In practice, the rain picked up, so we ended up going to the Shake Shack by the Brooklyn Bridge rather than try to scout out a fancier restaurant while getting drenched. We took our time eating, and managed to wait out the worst of the rain.

We walked by the water and did a little exploring around the DUMBO neighborhood.

Brooklyn Bridge

Once the rain had mostly stopped, we decided to walk across the Brooklyn Bridge.

The weather had scared away a lot of tourists, so it was actually quite peaceful and pleasant. We enjoyed the views of the city while the boys enjoyed looking through the cracks in the wooden slats.

Central Park

While we could have explored lower Manhattan, or gone to Battery Park, we instead opted to take the subway to Central Park. Lovely!

We wandered around the gardens a bit, then decided to walk along 5th avenue back to our hotel.

A Broadway Play

Our hotel was within walking distance of the Gershwin Theater, so after changing into something slightly spiffier, we set out to go see Wicked. Delightful! If you are looking for a new perspective to the Wizard of Oz, we would highly recommend this Broadway play!

We felt a bit safer going to the theater in NYC because they require a proof of vaccination (or recent PCR test) and ID to enter. To make it simpler, the city published a phone app – the NYC Covid Safe app, where you can scan the card once and show it on your phone, rather than carrying your vaccine card around. The NYC Covid website has the full list of up-to-date requirements and restrictions.

Note that the vaccine proof is required for museums and indoor restaurants as well. Also, masks were required in the theaters, and the ushers were (mostly) checking.

We had a great time, our teenage boys loved the play!

Day 3: Back Home

On Monday morning, I was feeling a little exhausted, but we went ahead and took a morning walk around Midtown.

The United Nations New York Headquarters

Our first stop was the United Nations New York Headquarters. During normal times, you can get a tour of the Visitor’s Center, but with Covid still an issue, they have paused the tours. Still, it is a lot of fun to walk along the outside and see how many different flags you recognize.

Grand Central Station

Next up was the Grand Central Station. The late-1800’s marble architecture is quite lovely and you should stop by.

New York Public Libray

In addition, we walked by New York Public Library, and the neighboring Bryant Park. We continued the morning walk by the Empire State Building, Macy’s and through Times Square as well (which feels quite different in the morning).

We circled back to our hotel a little before noon checkout, a bit tired from the weekend, and deciding that we should go home and prep for the coming week.

What a great weekend trip! If you live nearby, consider taking a road trip and spending a few days in New York City! And if you are traveling from further away, there is plenty to keep you occupied for much longer!

Keep reading our travel blog for more travel itinerary ideas!

Here are some more posts from this trip to NYC: