Planning Your First Solo Trip

How to take out all the fear so you can have all the fun

You want to see the world, have adventures, and travel “like everyone else,” but you don’t have anyone to go with.  This is a predicament that has plagued most single women at one point or another.  Either you don’t have anyone in your life with whom you care to travel, or your friends are all time-constrained, don’t have the money, or don’t want to go where you want to go.  You’ve considered traveling alone, but you’ve never done it before, at least not outside of a business trip, and the thought of planning and then actually going on a trip by yourself is intimidating and downright scary.  Even if you’re not scared, the thought of spending every waking minute alone for a week or even just a weekend may sound lonely and boring.  What if I told you I have a surefire way for you to have a single-girl getaway that doesn’t include fear, intimidation, boredom or loneliness?  The secret is to have a well thought out plan in place and take the guesswork (read: fear, anxiety) out of the process.  What’s the plan?  I’ll show you.  And soon you’ll be jet-setting with the best of them!

Step 1 – the where, when and why

The first thing you need to do, before you even decide where you want to go, is decide why you want to take this trip.  Do you want to explore an interest, like wine tasting or paddle boarding?  Do you want to see a particular sight or sights?  Do you want to try something new, like an outdoor activity or an educational program?  Or do you just need a relaxing break from your job and the rigors of day-to-day life?  The purpose of your trip will largely dictate where you go, so determining what kind of trip you’d like to take is number one.  Once you’ve decided this, you can determine where you want to go.  For your first solo trip, I recommend going someplace you’ve actually been before so that you’re comfortable with the area, and someplace you can drive to that’s less than four hours from your home.  I also recommend just going for an overnight on your first trip if you’re nervous about traveling alone.  You leave one day and you’re back the next, easy-peasy.  Is there someplace you’ve been to, but you didn’t get to try a certain activity or see a certain sight?  Did you see a fabulous spa resort the last time you were there and you’d love to actually stay there?  Or do you have a fave place you like to go, you’ve just never been by yourself before?  The beauty of the solo trip is that you get to choose the where and when without having to take into consideration someone else’s desires or timeline. Choose where you’d like to go and then choose the dates that work for you.

Step 2 – the how and what

The next step is of course to find a place to stay.  If you’ve been to this place before then maybe you already have a place picked out, or you can Google “places to stay in __________ ,” to get an idea of what’s there.  You can target a specific hotel directly, or there’s always Expedia, Priceline, Hotwire, etc, which will show you all of your available options.  Another option is to find a place through Airbnb or VRBO.  You can find places where you have the whole place to yourself, or you can also find places that are in the host’s home or attached to their home, if you feel safer this way.  Sometimes hosts take pretty good care of their guests and this could be a way to feel not-so-alone.  Once you’ve booked your stay you’re almost ready to go, but there’s still the question of what you’ll do when you’re there.  If you don’t have a plan in place you may spend the entire time reading in bed.  Now, if that’s your purpose for the trip then there’s nothing wrong with that, but my guess is you’ll be wanting to do more than that.  Decide what activities you want to do while you’re there and when you’ll do them.  For my first solo wine tasting trip I decided that I wanted to visit a certain number of wineries.  I also wanted to have dinner in a nice restaurant, go for a hike the following morning, and have lunch at a little café that I discovered the last time I was there.  I decided which wineries I wanted to visit on each day, made a list according to location, found a dinner spot online and made a reservation, and located a hiking spot for the morning.  I drove there in the morning one day, visited wineries in the afternoon, checked into my hotel then went for dinner, got up and went hiking the next morning, visited the rest of the wineries that day, stopping for lunch at the café in between, and then I was on my way back home.  It was the best trip ever and it was because it was all planned out with everything I wanted to do and everywhere I wanted to go.  Now, that doesn’t mean you can’t leave room for flexibility.  I actually swapped out a couple wineries on my list because someone told me about some new ones that had opened.  Have a concrete plan, but be open to spontaneity and you’ll have an amazing, fun-filled time!

Step 3 – the little details

Now that you have your place picked out, you’ve made your reservations, and you have a plan for what you’d like to do and when, it’s time to remember the little details that are going to make your trip worry-free.  Keep all your confirmation information in one place, whether it’s an email folder on your phone or a printed sheet of paper with all the info.  Having it in one place will keep you from frantically searching should you need it.  Have your activity plan written out, even if it’s just a note on your phone, so that you’ll know where you’re going next.  Make sure your car maintenance is up to date.  Do you need an oil change?  Tire rotation?  New wiper blades?  Is your AAA membership current?  Feeling confident in your mode of transportation is important.  It’s also a good idea to either have a printed map or at least know pretty much where you’re going just in case GPS fails you.  Finally, make sure your phone is fully charged and you have your charger, you have plenty of snacks and water, you’ve brought something to read if you have some downtime, your car is fully gassed up, your pets have their care in place, and you’ve locked the front door.  You’re on your way to your first solo journey!

Solo travel doesn’t have to be intimidating, scary, boring or lonely.  With some preparation and the right plan, you’ll have an enjoyable trip and wonder why you waited so long.  There’s no reason you should have to retire your suitcase just because you’re single.  Single women travel solo all the time and you can, too.  Make your first trip as safe and comfortable as possible, and soon you’ll have the confidence to go farther and stay longer.  You’ll be planning that solo trip to Paris in no time!

To take the worry and guesswork out of planning your first solo trip, get the “Your First Solo Trip Checklist” free download that will take you through the planning process step-by-step so you can travel with confidence.  When you have a plan in place you can relax and enjoy your trip anxiety-free!

Leslie Kaz, coach for single women

I help single women get from where they are to where they want to be by overcoming their sadness and starting to live their best lives through mindset and lifestyle changes. Contact me to learn how it’s possible to live a single, blissful life.

Single Girl Bliss Book Cover

Create your life plan and
start living your most
blissful single-girl life.

Learn how to change your mindset and take action so that you can go from where you are now to where you want to be.