This is my first travel post and it is about pushing past the fear of solo travel. If you are a corporate road warrior (and I did my fair amount of traveling at CS STARS and Origami Risk) then you’re already comfortable with eating BLD (shout out to Joe Cannon/Seat 2A for that acronym) by yourself. You either grab a book, stare at your phone or sit at a bar that has a tv on, pretending to be interested in whatever is airing. But vacationing by yourself can be more daunting.

First, how did I end up by myself? Without the full gory details, I’ll give a brief synopsis. I’m done hiding (after all, this is the brave new Mary 2.0). I have no children. I wanted children and pursued ALL treatments with the final diagnosis being ‘unexplained infertility’. My analytical mind struggled with the lack of diagnosis – not knowing the ‘why’ won’t change the outcome at all – which, by the way, is some sage advice for you, so I’ll repeat it and bold/italics it for emphasis. Not knowing the ‘why’ will not change the outcome. The sooner you can accept and move on, the better/healthier for you. This lesson is one that I’ve had to learn and relearn many many times. Anyway, my husband had no interest in adoption. Apparently he also had no interest in staying married to me. So I found myself divorced in 2015. I’ll save that story for another post. There are lots of opportunities that life throws at you as a divorced woman. I won’t go into all of them, except for what this post is about – traveling/vacationing solo.

I took my first big solo trip to Hawaii back in 2018. This vacation only happened because Delta was having a deal on SkyMiles and Brad K basically told me I was being stupid by not using my points and I needed to suck it up and take the plunge. So I found myself on a long flight to Hawaii by myself, followed by a few days in Oahu and a few days in Kona (yes I even island hopped). I learned on this trip that the flying piece is easy – especially today when you can watch movies that you want to watch for hours on end (who here remembers flying where there was one screen shared by everyone and the mad rush as the credits rolled to get to the bathroom before massive line formed?).

So let’s talk about the opportunities (you see how I don’t call them obstacles or challenges). But first, let me share the AMAZING view from my room at the hotel Halekulani…

…along with the welcome from the hotel

I can highly highly highly recommend Hotel Halekulani and will post a few pictures at the end, but let’s focus on the task at hand.

So the challenges…er…I mean opportunities. Hawaii is a honeymoon/couples vacationing kinda place. So perhaps not the best choice when going solo, so I recommend thinking through that for your first trip only…and now the truth that will set you free – IT DOESN’T MATTER. You are on this earth only once. If you want to go to Hawaii, GO! Please allow me to quote Auntie Mame – ‘Life is a banquet and most poor suckers are starving to death! LIVE! LIVE! LIVE!’

The fears I had and how I tackled:

  • Eating by myself – I had some help, having done this for business.  The above options (bring a book, stare at your phone, go to a sports bar) all work…but let me share a few more. 1) many restaurants have a bar area where you can sit.  Don’t be afraid to do that and strike up a conversation with the bartender or the person sitting next to you.  EVERYONE has a story to tell, your job is to get them to tell it. 2) many restaurants have a singles table, so ask the host/hostess if they have one.  3) many places have a combo dinner/show where you can be entertained while you eat and it won’t be as ‘obvious’ that you’re by yourself.  Whatever you do, don’t get trapped in your room ordering room service. If you want to stay in your room, you should have stayed home. 
  • Venturing out by myself – for this trip, I planned out a great deal of it ahead of time so that I had a plan for each day (including a day  to sit on the beach, so don’t over-plan and exhaust yourself).  Do your research and confirm if there are shady areas (none that I know of in Hawaii).  Also check in with the front desk or concierge, they’re usually quite happy to tell you places to go.  I had one hiccup in that I asked a couple for suggestions, which ended up having more of a ‘couples’ flair to it.  E.g., they recommended a tour guide for a trip..I booked it not realizing it was private, just for me.  It actually made me feel a little like a celebrity, but did have some awkward moments.  From a safety standpoint, as a female solo traveler, I would recommend sharing your day’s activities with someone.  I always texted my sister to let her know where I was that day and when I would be back, just in case… (Life is about risk management).  She also had a copy of my itinerary.  A bonus if you build out an itinerary is your scrapbook/photo collage is much easier to create!
  • Emergencies by yourself – this really isn’t exclusive to solo traveling, but I will put here. If you are feeling exceptionally concerned, google where the nearest police and hospital are.  I personally have never done that, but I write it here as a risk management professional. If you’re going international, know where the embassy is, know where your passport is at all times. And listen to your spidey senses – if your gut is telling you to be concerned, trust your gut.

My next two big trips are Canada and Eastern Europe.  For Canada, a friend and I are traveling together for the first time.  I am positive that trip will produce at least one good post here.  For Eastern Europe I’m going on a river boat cruise.  I am mildly concerned about that trip as it will be quite obvious that I’m a solo travel – and I’ll be with the same people for 10+ days. I’m an extroverted introvert or an introverted extrovert…either way I’m going to get over my shyness and insecurities and meet people and LIVE! LIVE! LIVE!’

And because it is Hawaii – I’ll end with a few pictures!

Two of those are from my helicopter tour.  Very nice (but be forewarned they make you weigh in so that weight is properly distributed. 

Leave a Reply

Your email address will not be published. Required fields are marked *