Planning a Solo Vacation?  Ask Yourself These 3 Questions

When someone asks me, “Where should I go for a solo vacation?” I rarely start with a destination.

I start with the traveler.

In many ways, I see my role as part travel advisor, part matchmaker.  Before recommending where to go, I want to understand how you want the experience to feel.

If you are considering solo travel, start with these three questions.

1.  What do I want this trip to give me?

Adventure?  Rest?  Cultural immersion?  Connection?  Or simply uninterrupted time for yourself?  All of the above?

Think about what you naturally enjoy and what you may have been putting off while waiting for someone else to join you.

One of our clients, whom I’ll call Lawrence, came to us planning his first solo vacation.  At first, he wanted to get away.  As we talked, he realized he wanted culture, a little adventure, a culinary experience, and a professional tennis match—but no packed itinerary or lengthy museum tours.

His trip became less about escaping and more about reconnecting with things he enjoyed.

2.  How much interaction do I want?

Solo travel does not have to mean being alone.

Some travelers enjoy meeting people throughout their trip.  Others prefer occasional connection with plenty of time to themselves.

Lawrence wanted both.  He was comfortable dining alone and setting his own pace but wasn’t sure how he would feel attending a sporting event by himself.

We arranged a ticket to the Madrid Open (tennis tournament) with pre-match hospitality, so he could meet other tennis enthusiasts while maintaining the independence he wanted.

The goal is to find the right balance for you.

My clients give their referrals a heads-up and often joke to be prepared for my infamous follow-up question:

"Who are you when you travel?” — Michelle Green

It usually invites an intentional pause.

3.  What do I need to feel supported enough to relax?

For some travelers, luxury means beautiful accommodations or private experiences.

For others, the greatest luxury is not having to figure everything out on their own.

Thoughtful solo vacation planning may mean arranging centrally located accommodations, private transfers, trusted guides for private tours, or even a guided tour.  Knowing you can have in-destination support if you need it, while still leaving room for spontaneity, is a win-win for several of our clients.

The Best Solo Destination Is the One That Fits You

Countless lists rank the “best destinations for solo travelers.”

I prefer to start with a different question:

Who are you when you travel?

Once you understand what you want from the trip, how much interaction feels right, and what support helps you relax, choosing the destination becomes much easier.

I’ve had to answer these questions for myself, too.  Those who know me well know I prefer to appreciate the outdoors from indoors!  But one year, I craved a closer connection to nature and was ready to “rough it”; well, my version of it.  That November, I traveled to Iceland and stepped outside my comfort zone in more ways than one, while still staying within a range that felt right for me.

That trip gave me everything I wanted and more.

The best solo vacation isn’t simply about going somewhere beautiful.  It’s about creating an experience that feels like you.

If you’re still figuring out what that experience looks like, Conversational Traveler can help.

Author Bio

Michelle Green, ASTA Verified® Travel Advisor, is the founder of Conversational Traveler and an NYC ASTA Board Member.  Conversational Traveler specializes in celebration and bucket-list journeys.