Hindsight Is Literally 2020!
Hindsight Is Literally 2020!

So as I was approaching my 57th birthday this past October, I came to realize that travel has been on my bucket list 40 years and that since my divorce 6 years ago, I have somehow always felt like I needed someone to give me permission to do so. Really, permission, at 57…why?

Do not get me wrong, I have traveled plenty. Greece for my 40th was special, Spain and Morocco were life changing and celebrating my daughter’s 16th birthday driving across Europe just the two of us will always rank as one of my all-time joys. Even an unexpected, quick trip to Cuba with my 27-year-old son was filled with more laughter than I can describe. Cuba, where the rum is cheap and the music never stops is where I did my best to keep up with him and considered myself a trooper for staying upright the whole time! This was on a trip where keeping up with a 27-year-old who loves to laugh like his mother left me needing to detox for a week upon our return. All worth it and highly recommended.

Now, even with all those great trips from the past, turning 57 during a Pandemic and having a thirst to explore like never before, left me with the reality that if travel was to happen, I was going to have to do it alone. I would have to go solo…and so I did.

Deciding where to go for my 57th was easy: St John, Virgin Islands. The desolate beaches, turquoise water and free spirit of the island people was just what the doctor ordered. I had  been there several other times with my kids but this trip would be different.

I knew exactly what I wanted—warmth, isolation and calm. Staying up on a hillside bungalow near town and driving around in a blue jeep wrangler in nothing but a bathing suit, cover-up and sandals was pure perfection! My five days there began every morning briefly connecting with the co-workers via a conference call.  It was my personal choice to work a little as I found it helpful in creating some continuity for myself in this otherwise very fluid and ever-changing time. It somehow grounded my day and allowed for the rest of it to be free and flowing with no specific plans and no guilt should I choose to do nothing all day. It was the perfect way to celebrate another year and a safe way of doing it. I would not change a thing and learned a few new things along the way. Here are my takeaways:

Visualize, plan what you picture and make it happen

Whether you like lots of activities or beach time, plan your trip around what matters to you. Have a visual of what you want and then go for it. I love the water and hot weather, so an island trip was perfect for me. I didn’t want to wear heels and being close to nature was important. The beauty when traveling solo is that you get to create your own experience and don’t need to consider anyone else in the equation. This is one time where being selfish is a good thing.

Think safety…it’s all about you

Selecting a hotel or resort that is located in a safe place is very important when traveling solo. Do your homework by reading reviews, spend more money if needed, and always stay alert with your surroundings. Own your space, stay aware but don’t let fear dictate your decisions.

Take yourself out on a date and eat what you want

Ahh…to eat and drink to your heart’s content! Solo travel is not about dieting or watching your weight. If food and eating is part of your experience then make it so. Picking good restaurants by asking the locals is always a good start. Dress up and take yourself out on a date every night as I did. After my second night, I came to realize that I am actually pretty good company and didn’t feel like a “fish out of water.” I really like my own company and having the freedom to pick for myself was so much fun that I can’t wait to do it again! Every night was a new place and a new adventure.

Go with the flow and throw away your agenda

When planning your trip, stay fairly loose with your plans. Some things, like airfare and hotels, do need planning, but the daily activities should have some wiggle room. I picked my flight and hotel/resort but nothing else. When I got there, I figured I would taxi around, as driving on the left side of the road was foreign and intimidating to me. I didn’t plan to rent a car yet after less than 24 hours there I decided to face my fear and rented a Jeep. It was the BEST decision I could have made as it allowed me to explore on my terms. It also taught me that my fear was unfounded, after all, I drive in Miami every day and drove throughout Europe for two weeks a few years back.

So, as we’ve wrapped up 2020 and think about all the loss, pain and grief of so many, also take the time to reflect on the clarity it gave you and how seeing things with a clear vision can be the best hindsight for 2021. As a result of my experience, I will be solo traveling my own Yellow Brick Road from here on out. Don’t wait for permission and don’t even wait for a birthday. Don’t hesitate to be your best dinner date, just pick a place and go!

Related content:
Travel Expenses: What You Need to Know
Work Travel + Life = Chaos?
Traveling? Protect Your Identity and Credit


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