How to Plan Your First Alone Trip

Female solo camping in Oregon

The Flexible Approach to Your First Planned Vacation Alone

#1. Set an amount of money you can spend and be realistic
#2. Write down five things that you remember you used to love or think you could love
#3. Request the PTO off, even if everything isn’t planned out yet
#4. Choose a place based on the list you created in step #2
#5. Create a list in the Bear App of restaurants, cafes, and local attractions that interest you around that place
6. Book where you’re staying
7. Add the places from Step #5 to a Google Map
8. Check your car before you go: oil, gas, windshield wiper fluid, tags, license, and toll money

Every year people start off New Years Resolutions to motivate them to be the person they want to become. For me, I started my New Years Resolution back in July, where I woke up one day and told myself that it was time to stop making excuses for not doing anything fun and exciting with my life. I wasn’t sure who I wanted to be, but that I wanted to challenge myself to have unique experiences.

#1. Set an amount of money you can spend and be realistic

There wasn’t a huge budget to spend; to be honest, I had about $270 to spend and while that’s not much for a vacation, I had to make it work; I NEEDED to take a vacation. With $270, I had enough to really enjoy myself and turn my terrible 2019 into a stellar year from this one trip.

#2. Write down five things that you remember you used to love or think you could love

So, I decided to just start with what I knew I used to love– water and camping. The smell of camping, the cold damp air at night, the satisfaction of laying down in your tent with snacks nearby, and the way the sounds of other campsites danced with your silence was such a peaceful experience. Those are all memories I adore from childhood. The beach was another. I grew up chasing the waves, burying myself in sand, tasting the candies from the corner store, the hot sun drying up your splashed skin– I bask in those memories even now. It didn’t matter which body of water, but the beach feeling mixed with the camp vibes seemed like a good place to start. So, I searched “beach campsites” into google and saw their top 10 results. “Tillamook, Oregon” was a place I recognized, felt comfortable with, and knew that I could explore on my own and feel safe.

#3. Request the PTO off, even if everything isn’t planned out yet

For me, I had plenty of PTO to spend, so I just spent it. However, that’s not always the case for people (including me!). If it’s not “I don’t have the money”, it’s always “I don’t have enough PTO”. So, how much do you have to make it work?
Maybe you only have a day of paid time off (PTO) in the bank, but your company allows you to take a half-day without penalty. Or, perhaps you have holidays off from work and could schedule well in advance to take advantage of that free day off. As an example, here is a calendar of all the holidays that my company recognizes. As a rule of thumb, when the stock market is closed, our company is closed; Otherwise, we’re open! Sometimes these rules of thumb make it easy to plan ahead without asking your boss too many questions about paid time off.

#5. Create a list in the Bear App of restaurants, cafes, and local attractions that interest you around that place

6. Book where you’re staying

The first time I ever booked a hotel by myself, I showed up to the counter and they asked to put a card on file. I gave them my debit card. There was $121 available in my bank. I had no idea that you needed to put a hold on the card. But, these are things you either hear from your parents, or you just figure out. Lucky for me, the Arthritis Foundation was sponsoring my trip, so the clerk nicely told me that he put a hold on the card for $100. In reality, he should have turned me away as a guest, but since the corporate account was on file, and it was a volunteer opportunity for children with disabilities, I think he did me a solid and figured I had to be a semi-decent person to be there at the hotel on the AF’s expense.

When it comes to booking where you want to stay, I always choose one local attraction that excites me and then I book the lodging fairly close to it. My first trip alone was paragliding. So, I booked my campsite within a short driving distance to the sand dunes so that I wouldn’t chicken-out. To my surprise, my campsite ended up being about a mile from the Tillamook Cheese Factory, the place with the best breakfast and coffee in town! An added bonus was how safe the campsite was– it had a large open field with plenty of families with children around, which made me feel safe. The site had good ratings, a quick response from the campsite owner, and didn’t require any cleaning fees, which was an added plus given I was on such a small budget.

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