A Single Baby Boomer Flies Solo in Manhattan


Are you afraid of traveling alone?  Even as a single Baby Boomer who’s traveled extensively, I’m still apprehensive before a solo trip.  To combat this I stay current on changes in technology and other travel advice.  I often read the many travel blogs about solo travel and have used some of their tips.  After investigating several popular travel and New York sites, I decided I could tackle Manhattan on my own.  I had my GPS to help me find subways and buses and even steer me the right way as I walked and the Uber app on my Smartphone.  There were many more apps I could’ve downloaded, but I felt I was good to go.



Since I’d been to the Big Apple 3 times before, don’t enjoy shopping and have been in museums all over the world, I decided to go with the Hop-on Hop-off bus to get an overall view of the city.  I was delighted to find my timeshare offered me a free Big Bus ticket and a cruise around Ellis Island and the Statue of Liberty.



When I arrived at Penn Station on Amtrak from Providence, RI after five days with my friend touring mansions and eating lobster in Newport and on Martha’s Vineyard, I pulled up my Uber app and headed for the information counter.  The young man helped me set up my ride before I headed out the door.  I’d practiced the app before, but this was my first real ride so I found a Millennial.  They’ve mastered their Smartphone and a multitude of apps.  I find they seem to like to help a Baby Boomer who probably reminds them of their grandmother.  There I was alone in a major metropolis, on the street where I was supposed to meet the car, but which way should I go.  Madison Square Garden is next to the station, so I asked a security guard which direction I should head.  He told me to go right and wait at the end of the street.  By the time I got there my Smartphone told me the driver would meet me at another corner.  I asked a well-dressed 30-something business man and he ignored me, but a Millennial came up to me, told me how to find the name and picture of the driver, the car make, and license number.  I was then able to call him and arrange, with the young man’s help, the correct side of the street to meet him.  Believe me, I never even considered that I needed to know if I was on the east or west side of the street.  FYI-Uber drivers text you when they’re getting close and have your picture to help find you.



I could go on at length about my Uber experience, but suffice to say this driver and the one who took me to the airport were excellent and took me right to the door.  Anyone who drives in New York has to have nerves of steel and limitless patience.  The fact you can now use credit cards with Uber and taxis makes it easier to get around.  Buses do need change if you don’t have a bus pass and you can buy a MetroCard for the subway.  I didn’t use the subway there but have used it in many cities and it’s easy if you’re not afraid to ask for help.  See http://www.wikihow.com/Ride-the-New-York-City-Subway.


My efficiency condo at the Wyndham Midtown 45 at NYC had a full kitchen complete with a dishwasher.  Since I had all of the things necessary to make a complete meal, I didn’t eat out but I never feel uncomfortable alone in a nice restaurant in a safe neighborhood.  I sometimes sit at the bar and find there are often people who are happy to share their experiences and advice about their city.  I have a new love affair with delis where you can find a wide selection of both hot and cold food.  I know NYC is famous for many types of delicacies, but my favorites were the cheesecake and lox and bagels.  I found out the hard way that you need to check your food since when I got back to the condo I found one of my sandwiches was just a bagel, cream cheese, onions, tomato and no lox.  I don’t know if it was a miscommunication due to a difference in languages (New York is indeed a melting pot of cultures and languages) or a lack of attention to detail on the server’s part, but it was an expensive sandwich even for New York.

Lox and Bagel

The Big Bus Hop-on Hop-off bus tour ended up being a stay-on and hop-off for lunch and a change of bus tour.  It took over six hours to accomplish that but even in the light drizzle it was enjoyable.  There are two loops, upper and lower Manhattan.  The tour guides, Carl and Ross, were knowledgeable but Ross brought his Italian-American comedic spin to his tour so it was extremely entertaining.  He described his presentation as facts with some “bullshit” thrown in.  On tours in other cities, I hopped off, but with my limited time and a desire to see the highlights, I found my choice worked out well and if you’re afraid of getting lost, it’s a good choice.  You can get an overview and then decide what you want to see another day.  Multiple day bus tours are also available. See http://eng.bigbustours.com/newyork/home.html.

The Big Bus in Times Square

The next day, with the help of Google Maps and the doorman, I found a bus route that took me right up to the pier for my guided Liberty Cruise.  I arrived too early for the tour and spent time at The Intrepid Sea, Air & Space Museum touring the decommissioned aircraft carrier, Intrepid and the Space Shuttle display featuring the Enterprise and a live presentation on how Star Trek influenced and was influenced by past and present inventions.  Did you know that theoretically in order to be “beamed up” they’d have to heat your atoms to a thousand degrees Fahrenheit, so they’re going to have to improve the technology?  In addition tours of the USS Growler submarine, Concord and a Star Trek Training Experience were available, if my schedule had allowed.  I especially enjoyed seeing the vintage military aircraft on the flight deck.  Even the rain didn’t dampen my enthusiasm. See https://www.intrepidmuseum.org/The-Intrepid-Experience/Guided-Tours.aspx for more information.

The Intrepid
The Intrepid


Ellis Island
Ellis Island

Times Square was busy on Friday night.  I was there during the Columbus Day Holiday Weekend and on Saturday night it was crazy.  Traffic was almost at a standstill when I got off the bus tour so I had to fight my way down to my turn onto 45th Ave and 7th Street.  If you like the energy crowds bring, I say go for it, but I was glad to get out of the area.  I suggest seeing it on a weekday.  The afternoon is less busy but the lights and videos are more vibrant in the dark.  Don’t be afraid to be out after dark even alone, but stay in populated areas.  Always protect your purse by holding it close to your body and don’t keep your wallet in your back pocket.

Times Square
Times Square

I could’ve seen a Broadway show, but since I’d done it before and the ones I wanted to see had astronomical price tags, I skipped it.  If you want to see one you can get discount tickets at the TKTS Booths.  They have a Smartphone app and a website with additional information at https://www.tdf.org/nyc/7/TKTS-ticket-booths.  You can also call theaters between 8 and 11 a.m. the day of the show to be entered in a lottery for discount tickets.  Your best bet is to go online to the many websites that offer discount tickets because of the line at the TKTS Booth, at least when I was there, was longer than the most popular rides at Disney World.


Sadly, I had to leave Manhattan on Monday.  I was surprised to see 3 service men with military assault rifles by the entrance to my terminal at LaGuardia Airport.  I haven’t experienced that in other U.S. airports, but I know there must be others that use the military in addition to airport security.  The 9/11 Memorial in New York reminds us of the need to protect ourselves from terrorist, both homegrown and from abroad.

9/11 Mem
9/11 Mem


Here are some takeaways.

  • Plan ahead and be flexible. As I mentioned before, I planned my trip in advance, but I had to revise my plan for the bus tour and cruise when I found the information I received at my condo was inaccurate.  I found it was easy to adjust my plans with my Smartphone and the aid of tour representatives.  Even other tourists can give you suggestions on places you might want to see.


  • The natives are friendly. They’re willing to help most of the time.  It doesn’t take long for you to get more aggressive if you think you’re not getting a fair shake.  Above all, though, be friendly and thank them for their help or service.  You get what you give.


  • Doormen/women give the best directions. They can also make sure your Uber or taxi appears when you need it.  The people at the desk or even the concierge don’t know the city like they do.  I always ask a couple of people just to make sure I have the right directions, but the doormen are always the most knowledgeable and patient, in my opinion.


  • Walk as much as you can and walk purposefully. If you’re able, walking is the best and quickest way to get around.  Traffic is usually horrendous and can be harrowing is you’re not a seasoned city driver.  I’ve driven all over the U.S. and abroad, but I walk or take public transportation in NYC.  Act like you know where you’re going.  You already asked for directions at your hotel and have a GPS, but if you’re really lost ask someone at an information booth, in a shop or a restaurant.  Don’t make yourself a target.


  • New York is accessible to people with disabilities. The Americans with Disabilities Act (ADA) assures that everyone can access transportation, sights, attractions, and lodging.  See http://travel.aarp.org/destinations/united-states/new-york-city/travel-tips/disabilities-and-accessibility/.  NYC The Official Guide at http://www.nycgo.com/plan-your-trip/basic-information/accessibility offers a free brochure to download with all the information you need to make your visit easy and memorable.  I visited with a man using a walker on a bus who was going to church.  The bus driver told him the best stop and way to get there once he got off the bus.  Crowded streets do make maneuvering difficult, but if you out early in the day, you can get most of your touring done before it gets too congested.  If you’re a clubber or going to the theater in the evening, an Uber or taxi may be your best option.


  • Be aware of your surroundings. Find out the safest places to sightsee.  This is usually the places out-of-towners want to visit so they’re crowded, but there’s safety in numbers especially at night.  In my experience, most tourists look out for each other.  There are always thieves in crowds, so keep your valuables hidden and in a wallet which doesn’t allow them to be scanned.


  • Smartphones are a smart choice. Not only do they allow you to communicate with others over an ever-expanding variety of apps, they can help you navigate, book tickets, check your credit card and bank balances, check-in at your airline, take excellent photos and give you a weather update.



These tips worked for me, but to tailor your trip to your wants and needs search the internet.  It’s a treasure trove of information.  When you plan your vacation keep in mind your budget, schedule and the attractions that interest you the most.  No matter how much time or money you have, you can never see it all.  If you’re a foodie, remember many restaurants have menus on their website.  You may want to reserve a table if you’re on a tight schedule.  Read unbiased reviews on eateries, hotels and the sights on TripAdvisor and Yelp. I found you either love New York or it’s a great place to visit, but wouldn’t want to live there.


While my trip wasn’t an amusement park thrill ride, I did what I wanted to do when and how I wanted to do it.  Although I always enjoy trips with friends, sometimes I need to stretch my boundaries and keep my edge by venturing out on my own.  My advice is to never be afraid to travel solo.  Just keep these tips in mind and enjoy your life as a single Baby Boomer.


Continue the adventure!

Linda Lea

2 thoughts on “A Single Baby Boomer Flies Solo in Manhattan

  1. Baby boomer born and raised in the Big Apple, I loved hearing of your experiences…pictures and a positive time in my hometown! Felt good and heart-warming to ‘feel’ the beat of the City from another perspective. Thank you for posting!


    1. Dear Virginia,
      Thank you for your comment. It is a wonderful city filled with caring, helpful people. It’s nice to hear from one of them.
      I hope that other visitors will take advantage of New York’s historic, cultural and culinary highlights.
      With kind regards,


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s