Planning Your First Solo Trip Step 1

Revised 4/2/20

You’re ready to start traveling solo for the first time.  Great! You’ve been reading online articles and blogs about what’s important and what not so important in solo travel planning.  You may start to feel confused or overwhelmed.  Understandable, especially if you’re venturing beyond your comfort zone. So where to start? At the beginning! Here is my, planning your first solo trip Step 1.

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Your Solo Trip Experience Over 40

Having done a lot of online travel research myself, I, too, have come across others’ opinions on how much they prepare, or don’t prepare, for a solo trip.  I notice some that write, “I like to be adventurous and wing it.”  I can identify with that feeling as an experienced solo traveler, but personally, I normally feel that if I’m returning to a place I know as a solo traveler.  To a new place, however, I’m not the “wing it” kind of person. As a first-time solo traveler over 40, I wouldn’t recommend it for you either.

Paris France_Eiffel Tower View

Planning Your First Solo Trip – Personality Checklist

There are different points of view, so as a first-time solo traveler, my humble advice would be to stop and ask yourself some basic questions first:

What kind of person am I?

Are you the type of person who likes to know where you are at all times, or do you revel in just wandering and getting lost?

Am I usually the designated planner or organizer?

Do you find the “devil in the details” fun, or is it too stressful to have to try to think of everything?

How do I enjoy my relaxation time?

Is being surrounded by a lot of people your idea of fun, or do you prefer to be in small groups of people, or even alone?  Additionally, even if you prefer to be around others, are you OK being alone?

Is money (and/or time) “no option”?

Is this your “once in a lifetime trip”, or do you know you can always go back?

Making a small checklist of your answers to the above questions will help guide you on how to proceed to book a solo trip that is right for you

For example, say you are fine being by yourself at all times.  You enjoy the freedom of doing whatever you want whenever you want but don’t mind hanging out with groups sometimes. You are saving all of your pennies for this trip and want to make the two weeks (or whatever amount of vacation time) the best they can be because you don’t know when you’ll get this opportunity again.  If this is you, then I would suggest planning as much as possible, from flights down to the days’ activities and costs. 

Checklist for planning your first solo trip
Make your checklist

Solo Travel or Group Travel?

Pricing and Activities

Research some group tours just to see what they offer in terms of activities, and cost compare against as if you were to do all of the planning and booking on your own.  You may find that you can see all you want to see in a fraction of the price that a group tour may charge or vice versa. 

Plus, when you are with a group, remember you may not have the flexibility to take off for a day on your own if you’re feeling up to it.  Keep these things in mind when you plan your first solo trip. 

If you really want to go alone on your first solo trip, don’t be afraid to consider a one-day group tour, such as those found on As a solo traveler, I find they have many great options to choose from at reasonable prices, which I love.  Who doesn’t like being a savvy traveler?  These daily tours also give you a chance to meet like-minded people, which I also love! After all, a solo travel benefit is having the opportunities to meet new people.

For example, at the last minute I found an amazing one-day wine tasting trip to the Wachau Valley outside Vienna, Austria and met a lovely, solo, female traveler from Denmark.  When we returned to Vienna she and I went out for dinner and drinks.  We are also connected on Facebook.

Trip Planning Help

Say you’re the person who finds looking for hotel deals or researching the best museums monotonous.  You know you want to see the city highlights but could not be bothered with where you’re going to eat or if the Louvre is better than the Musee d’ Orsay.  I would say you may want to try a group tour. 

Whether or not you enjoy groups, you can find tours that are geared towards smaller numbers (groups of 10 instead of 30).  Even if money is no option, I always recommend shopping around for the best deal.  If you feel the trip didn’t “do it for you”, ask yourself what you thought could have gone better? You can address those trip “misses” on the next visit (nudge, nudge). 

Eiffel Tower lit through the trees Paris
Eiffel Tower

Know Your Trip Priorities

No matter if you do a group tour or travel solo on your first solo trip, I would still advise at least knowing your tourist “bucket list” of activities, and your “backup” activities, before even booking a trip.  Don’t be afraid to ask for opinions or details on websites – most travel sites and bloggers provide areas for comments or reviews for a reason. 

Ultimately, the goal is to try get what you hoped for from the trip.  If you wish to go to the top of the Eiffel Tower but your tour group will only be on a bus driving by it, then you’re obviously going to feel disappointed in Paris.  It would be a waste to feel disappointed in Paris. Trust me.

Let Me Hear From You

I would love to hear if this post was helpful to you. Post me your thoughts or questions in the Comments section below. Thank you!

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