To be precise, hanging out, eating, and working remotely within a five-block radius of Midtown Manhattan.

A colleague from New York was kind enough to invite me to a client meeting on 5th Avenue this month. I thought, Clients on 5th Avenue?! It sounded exciting.

While I love working from home, I see going to meet colleagues, clients, and friends as some of the most valid reasons to leave the house. Relationships are one of the most important parts of doing business and being alive, and there’s nothing quite like in-person interaction.

5th Avenue is an iconic place of prestige, fashion, and culture. New York City overall is an amazing place to explore on foot, eat, and people watch. To sweeten the adventure even more – my family would be coming along, too. I jumped at the invitation without thinking twice, and a week later, we were boarding a plane to La Guardia Airport in New York.

Taking pics in front of the fountains at Chase Bank.

Heading To New York from Orlando

We chose Delta as our airline and flew out of Orlando. Leaving our SUV at a nearby parking lot instead of parking at the airport was a great way to start the trip – we were quoted only $44 for 4 days for covered parking and the shuttle service by Fast Park & Relax. The shuttle picked us up instantly from the exact spot where we parked. Given the 95+ degree Fahrenheit weather that day, it was much appreciated.

As we embarked, my husband and I agreed that it was weird to be leaving Florida to spend time somewhere else. I’ve been a resident of Florida for 15+ years and I’m still not bored of it. He’s still new here, but it truly is a great place to live if you enjoy a laid back lifestyle that produces a feeling that you’re forever on vacation.

But we were leaving Florida for a purpose, and we were excited.

Arriving at La Guardia Airport

After a slightly bumpy ride, we landed with a thud on the wet tarmac in Queens, New York. The temperature was 61 degrees and it was raining – I was sure we were about to freeze to death.

I was pleasantly surprised to find 61 degrees in NYC is not like 61 degrees in Florida. In Florida, if it dips below 70 it feels like you’re in a freezer. But at this temperature in New York, we were fine walking around with the same clothes we left Orlando in. That was a relief.

There’s a well-organized system for catching a yellow cab from the airport to your destination. You’re directed to Ground Transportation by signs throughout the terminal, and there’s a designated shuttle that takes you directly to the Yellow Cabs. You’re then directed by an airport employee that leads you right into the capable hands of a driver who somehow seems to be waiting especially for you.

yellow cabs in NYC

This eased my worry about being a tourist and getting scammed by some crazy cab driver; a wariness I’ll never forget due to various run-ins with taxi drivers in New York in the early 2000s and more recently, in its sister city Cairo, Egypt. The cab had a remarkably transparent metering system integrated into the TV screen that kept you entertained while in the backseat, and the driver was friendly. It was raining and congested on our way into the city, so our trip cost us about $50. It was overall, a good experience.

I was born in New York and it’s where I spent a good part of my childhood, but I hadn’t been back for a long time. Even during my last long visit in 2005, I stayed in Brooklyn. I hadn’t set foot in Manhattan for ages.

Especially after 9/11.

Seeing the old houses, apartment buildings, bridges, and the dense gray fog that engulfed every high point as we drove into the city was like being greeted by long-lost family members. I felt like more of a familiar visitor than a native; I was nostalgic, comfortable, and impatient. I was ready to get rid of our luggage and go sightseeing.

Our Hotel

So, about that…

I’m going to tell you the good and the bad. We stayed in a 3-star hotel called Club Quarters. I picked it because it was the least expensive place near 5th Avenue we could find with a 4 + star rating on Google and Trip Advisor. The place was full of business people, probably budget-conscious like us. It was pretty clean and full of friendly people.

Our room was a penthouse on the top floor and was about the size of a shoebox. My son slept in a rollaway bed that when opened, made the room so small that you had to walk around it sideways no matter what you were doing.

The bathroom was less than impressive but it could have been worse. The view from our window was of the wall of an adjacent building which couldn’t have been more than 20 feet away. It was trimmed with some externally installed ductwork and taking it all in, I understood something very clearly. We were lucky to have found a place to stay in such a great location that could sleep 3 people for such a reasonable price: only $313 a night.

And that’s New York City for you. We spent $8 plus tax on a 6-pack of Smart Water during this trip and if we’d chosen to rent a car it would have cost us $40 per day to park it. (There was no need for a car during this trip, anyhow) New York is expensive, and there’s no getting around it.

Luckily, the hotel made up for it with their free latte machine, M&M’s, nuts, cold sodas, fruit, other tasty snacks, and very accommodating staff.

Food in Midtown

tsq brasserie and food vendors in nyc
A view of a 2-story bar, diner, and a street vendor from inside the Times Square M&M’s store.

Yes, I’m easy to win over — all you have to do is feed me. I married someone who loves food just as much. We’re also both spontaneous whenever we can be, so we made no plans prior to arriving. In fact, our only plan was to eat in as many restaurants as possible while we were there.

Let’s start with the food trucks. Unlike my memories of Manhattan from 15+ years ago, the “dirty water dog” carts seem to have been replaced by Halal food trucks which sell pretzels, hot dogs, Italian and hot sausages, and some eastern style rice dishes. Since I don’t eat pork it was nice to find this variety and be able to eat sausages for a change. There’s at least one Halal food truck on every major block, so you’re bound to buy from one of them even if you’re in the city for just a few days.

There’s a famous place called The Halal Guys that people were flocking to, but we didn’t get to try it. (We were too focused on searching for Italian). Something really obvious in Midtown is that Halal street food is now THE street food of choice.

I’m sure the reason for this is simple – street food can be a lucrative business, and obviously, the word has spread among people arriving from the Middle East. My husband met a number of Egyptians working on these trucks and it was interesting hearing their stories. It’s definitely not easy work.

I remember there being lots of kosher food carts when I was a kid, but we didn’t see any kosher places to try. That was a little disappointing since we were looking forward to them, but maybe we didn’t explore enough of the city to find them.

We went to a couple of Irish pubs while we were there, Sean’s Bar on W 48th Street and Connolly’s near our hotel. Both were pretty good. They had fresh-tasting home cooked food. At Seans, they had a collection of in-house-brewed beers. If you ever visit, you have to try the Pilsner. It’s really good. Their fish and chips was also nice.

In general, the quality of the food in NYC when it comes to ingredients and preparation surpasses Florida’s by a mile.

Where else did we eat?

Pasta Lovers, on W 49th Street which was more expensive than it was good, and TSQ Brasserie on 7th Avenue. They have an average of a 2 star rating from visitors but we tried it anyway. The food was definitely diner-quality: surprisingly good European-style breakfast potatoes with well-seasoned scrambled eggs, strangely spongey pancakes (but they weren’t too bad), and mediocre coffee and tea.

The food may be better but service at typical restaurants in NYC feels a little off compared to the South. Everyone seems to be in too much of a rush and you don’t get a good sense of being welcome, to be honest.

However, I can’t forget to mention Little Italy Pizzeria on W 45th Street where my 10-year-old discovered the magic of real pizza. He doesn’t care for pizza in Florida; I actually have to insist that he eat it when we order it for dinner. But in NY, he became a pizza monster. It was crispy, greasy and perfect, and he finally understood the reason that pizza has always been my favorite food. The people working there were also super nice.

Places in Midtown

a street near Rockefeller Center
A street leading to Rockefeller Center. The FAO Schwartz toy store is on the corner.

We barely did any planning for this trip, and in my original hometown, I can’t bring myself to pay hundreds of dollars to enter into tourist traps.

What we did was randomly browse the area while not doing any real activities, per se. Let it be noted, this was lots of fun.

On Saturday morning we were pleasantly surprised by a number of outdoor markets that sprung up on different streets in the area. They were an urban version of the farmer’s markets that we have on the weekends down south.

Since coming back to the US from living abroad, I haven’t been able to make my way to our weekend market events because when I’m not running to my kids’ sports outing, I just want to chill at home. It was great to finally get out to one and achieve my long-standing, food-oriented, homecoming goals of getting an arepa.

If you don’t know, Arepas are a favorite Latin American treat – grilled cornbread with melted mozzarella in the center. There’s seems to always be an arepa stand or two at weekend markets. Honestly, Latin food is something that’s done well in Florida and I wasn’t impressed by the one I had in NY, but kind of like bad pizza, a bad arepa is still an arepa.

Besides food, there were trendy and bohemian clothing pieces, an array of knickknacks, and other cool things to see like a homeless man playing drums made of found objects with exceptional skill, in and around the clusters of tents.

Something that makes the Midtown-Times Square area wonderful is its family-friendly atmosphere, whether it’s early in the morning or late at night. We’re night owls and we’d go out at 10 o’clock at night to find it alive with of people from all over the world hanging out with their spouses, kids, friends, and whoever else. There are countless places to sit and observe, shop, and pick up novelty items – or things that are just plain useful.

We did get to visit some classic featured retailers which was awesome because they’re all 2 and 3-story mega versions of the branded shops you usually find at malls.

The Levi’s Store is full of NY-themed gear, (there was a sale on at the time to buy 2 tees for $29), the M&M’s store has really cute toys and clothes (my son got a cool black mug with a map of NY on it for $15), and The Gap also had good sales. They were all within minutes of each other on foot. Those are just a few examples of placed we popped in and out of, and they each had something for everyone.

A few blocks away, walking up 5th Avenue, we stumbled upon the St. Patrick’s Cathedral which was much more gorgeous inside and out than I’d ever realized.

We also accidentally found Rockefeller Center during one of our quests for pizza, and while we were there we made sure to go play in the world-famous toy store FAO Schwartz.

St. Patrick's Cathedral
St. Patrick’s Cathedral. Pictures do no justice to the beauty of this architectural masterpiece.

We got to see iconic Broadway and the Radio City Music Hall, and you can also see the new World Trade Center, Freedom Tower, with the naked eye from various points in the area.

I can’t emphasize enough how much more there is to do in this 5-10 block radius, but what we got to do was not bad at all for not having a plan.

Working Remotely in Manhattan

Although I enjoy flying because it’s one of the few times I enjoy in life I feel I can legitimately do nothing, I chose to buy Delta’s $15 per day in-flight Wi-Fi during our flight in to make good use of the time. The connection was slow, but it really helped me to get things done during those distraction-free 2.5 hours.

You don’t have to tell me – the airline WiFi had nothing to do with NY but I had to squeeze that info in for my fellow remote workers, somewhere 🙂

I had a horrible signal the whole time we were in Manhattan for my voice calls, text messages, and for my personal hotspot. I was missing or not able to make calls when I seemed to have full bars, I was getting text messages hours after they’d been sent to me, and I suffered through painstakingly slow page loads.

I have T-Mobile and I usually blame living in the Florida backwoods for my spotty connection, but being in a real city, it was actually much worse. From the various lessons I learned during this trip, one thing I learned is that I really need to think about changing carriers.

We made the mistake of attempting to work at Starbucks one block off of 5th Avenue. I ended up leaving in a huff of frustration when my computer died because both of the wall connections under the table where we sat were too loose to hold my power cord securely. And like all other Starbucks, their table was tortuously small for 2 people with 15″ laptops to work on.

It was annoying that Starbucks had music playing so loud, (again this is at all of their locations) but having to take a phone call while there led to the discovery that the noise-canceling microphone on my iPhone X works extremely well. The person on the other end couldn’t hear a drop of my ambient noise, even though it sounded like we were at a bar instead of a cafe.

Ultimately, it was most practical to work from our shoebox hotel room. The hotel had a lounge area where you can work if you got there early enough before happy hour to get a seat, and don’t mind not having any privacy.

We choose to go back up to our room and with a nightstand doubling as my desk away from home, and hotel’s decent free WiFi, I was able to get a little more than expected done.

In retrospect, there were some remote work spots we should have tried. There is an amazing 3-level Barnes and Nobles on 5th avenue that may not be such a bad place to work if you have no calls to make, and it’s also much quieter than Starbucks.

We also realized on our last day that we’d overlooked quite a number of quaint cafes nearby, including a chain called Pret A Manger that I’d never heard of before this trip. The one on W 45th Street near where we stayed seemed empty all the time. That may have made it an ideal spot to work, but the emptiness was probably also the reason we subconsciously ignored it.

In the end, I guess we’re creatures of habit and as much as we like remote work, we prove to ourselves over and over again that we enjoy working from home more than anything — wherever our home base may be at any given moment.

This trip to New York City was one of those vacations that despite some imperfections, really made us want to stay. Yeah, we saw a crazy lady working out like Rocky for all the world to see with no shame, at some point of each day the garbage started overflowing from receptacles, the streets got icky and littered, and everything is very costly. But New York is fun, alive, and homey.

My son summed up this feeling when we first arrived and he asked me, “How can people live on top of each other like this?” Five minutes later he was telling me, “I like it here – I want to stay.”

When will we be back? Who knows when the stars will align and a reason will appear for us to be there again, but we are looking forward to it. It’s up to you, New York.