travelling alone for the first time

Travelling Alone for the First Time – Solo travel for women over 50

Perhaps you’ve always had dreams of traveling the world.  But the funny thing about life is stuff comes up.  You fall in love, get married and have a family.  Maybe you’re lucky enough to travel to the closest entertainment park with your family every other year.  By the time the kids reach high school age those family trips are few and far between.

travelling alone for the first time

Or maybe you never married and you never found that special person to travel the world with.  And your single girlfriends hate to travel or they’re married raising a family.

Time flies. Life happens and now you’re a hot, foxy (but single) woman over the age of 50 who realizes you don’t want to wait any longer for a lifetime travel partner in order to see the world.  Or a married woman over 50; hot and foxy but your husband hates to travel.  I mean HATES  to travel but you want to see the world (or at least a few major cities in the U.S. or for God sake…Paris).

Then it hits you.  Now is the time. However, the thought of traveling alone for the first time is either (1) scary and depressing,  or (2) pisses you off because this isn’t the way your travel fantasy played out in your head.

Well, I’m here to tell you that the travel fantasy can come true.  But to make your travel dreams come true you will need to be open-minded. It might not look like what you thought it would be but it’s still going to be great.

Reason Why Women Over 50 Should Try Traveling Alone

There are plenty of young women traveling alone.  All you have to do is google “single travel for women” and you will see a shit-load of blogs about young female millennials traveling the world.

travelling alone for the first time

So, why not you, woman over 50?

If you think about it you have a lot in common with the single woman in her 20s; no children (because they’re grown), living on a budget (or maybe not) and ready; perhaps thirsty for a new adventure.  The advantage women over 50 do have over young millennial women is life experience (or let’s call it what it is; wisdom).  Life experience kicks young inexperience in the ass every time.

travelling alone for the first time

What millennial women do have over the women over 50 is the willingness to take a chance.  They haven’t had a lifetime of being told that you can’t or you shouldn’t because you are a woman.  Dream-crushing, I call it.  Or being told you sound crazy for talking about wanting a new adventure at your age.  Who does that?

This is the best time of your life. You have a sense of freedom now you’ve not experienced since your 20s.  You have amazing insight into who you are as a woman.  You’re strong, cool, wise and yes; foxy.  A-freakin’ female superhero!

So. Why not try solo travel?

10 Solo Travel Tips

travelling alone for the first time

So I’m not going to lie.  Traveling by yourself for the first time will feel a little scary; a little weird.  To make it feel less…umm, scary and weird I recommend the following tips:

  • Shore up your confidence with a day trip or two or three – to ease into the whole solo travel thing.  This is a great way to build up to going on longer trips.  It will also allow you to gain confidence in yourself as a solo traveler.  Some of my coolest day trips were right in my hometown of Chicago. Every once in a while I would spring for a room at a nice hotel in the downtown area and do an overnight stay.


  • Create an itinerary –  that will keep you stimulated visually, creatively and actively.  Create a schedule of your activities to follow but feel free to veer off should you find something along the way you want to explore or try.


  • Share your itinerary – with a family member and/or friend. And it wouldn’t hurt to leave a copy of it in the hotel room or at the hotel’s front desk…just in case.  Use technology (your smartphone) to check in with family and friends, periodically while on your journey with a quick text, email or phone call.


  • And speaking of safety – Always, always be present mentally and aware of your surroundings.  Go with your gut.  If a situation feels unsafe; abort…abort.  There’s nothing wrong with being extra cautious when traveling by yourself.  As tempting as it might be to wander around a city at midnight (don’t laugh…I’ve done it) its probably not a good idea.  If you want to go out after dark to take in a concert or the ballet, take Uber or a taxi.


  • Travel light – I recommend resisting the urge to overpack and carry a backpack.  You will love the freedom of not lugging a suitcase everywhere and it decreases the chances of lost or stolen luggage.  Read my article on the benefits of traveling with a backpack by clicking here.


  • Open a checking account dedicated to travel expenses – put away money in a special checking account for your travels.  This will keep you on budget and you won’t be tempted to gamble away your rent money (done this too in Vegas).  Make sure you have plenty of extra cash in this account for emergencies.  Having a dedicated travel credit card is great also.  However, I recommend only utilizing the credit card to hold your hotel room reservation or for any financial holds, the hotel will likely put on your card.  Once a trip is over, you should only have good memories and amazing travel pictures; not expenses that you now have to pay off.


  • Pre-purchase tours and other activities – before leaving for your solo trip. This way you don’t have to worry about dipping into money earmarked for expenses while on your journey. However, leave room in the budget for those last minute decisions to do tours and/or activities that were unplanned.   Again, use your smartphone to store digital tickets, i.e., airline tickets, tours, etc. on your device.  This will cut down on “oh, shit I forgot my reservation number”.


  • I recommend downloading the following apps: Google Maps, Yelp and Uber


  • Make physical copies of your passport, driver’s license, birth certificate – and any other important travel documents just in case you lose them on the way or they get stolen you will have a copy of it.


  • Don’t be afraid to ask for help when needed –  Know when to put on your big girl panties and work through any anxiety and when it’s truly okay to reach out someone.  Use your woman’s intuition and seek assistance or someone to talk to if you start feeling lonely.  I’m an introvert but there have been times during a trip when I’ve struck up a conversation and was rewarded with some amazing insight into my life or someone else’s.

Here are some other great articles to get you started on your journey:


travelling alone for the first time

Solo Travel Trips – Best Places to Travel Alone

For the first time solo traveler, I recommend traveling locally first then spreading your wings across the U.S. Here are some solo trip ideas to get you started!