Happy holidays to you, happy birthday to me
Taking a solo birthday trip in December has become my tradition, but this year I did something a little different.
If you’re like most people, you spent some time this December traveling to visit faraway family or friends for the holidays. If you’re like me… you didn’t.
Celebrating my birthdays with solo travel
My birthday is in December, and ever since my 25th I’ve taken a trip over my birthday. It started by happenstance. I wanted to get an Amtrak USA Rail Pass and take the train from coast to coast, and the easiest time I could take two weeks away from grad school was over winter break. That year, I spent my birthday on a train from Sacramento to Portland eating slightly stale donuts for lunch but ending my day at a bougie hotel with a bottle of wine and balloons.


Since then, birthday trips have included Copenhagen, a fancy hotel in Pittsburgh, and the new casino in Boston!
I invited a friend
As someone who clearly enjoys solo travel, it’s no surprise that I’ve enjoyed celebrating my birthdays doing exactly what I love. This year, I had already decided I needed to go somewhere sunny in December, and booked my birthday trip to a highly recommended resort in Aruba. Then, I invited a friend.
In the back of my mind, this trip always had the potential to be my first non-solo vacation since 2013 (which was not a favorable experience). I booked a two-bed room, then started wracking my brain about who I thought I could enjoy traveling with or whether I’d decide to travel solo, after all.
I was talking about my birthday trip plans with a friend, and on a whim, invited her to come. She quickly said yes!
Planning for a non-solo adventure
Throughout planning for and taking this trip, I learned a few key takeaways for the solo traveler not traveling alone:
Pick the right kind of trip. A resort trip felt like the right kind of reentry into non-solo travel. It’s a relaxing environment with plenty to do, or not do, right at the resort. A very busy sightseeing trip with a lot more options would have been too stressful and likely would have brought forth a lot more differing opinions about what we should do.
Discuss expectations up front. As a seasoned solo traveler, it was important that I had the option to do some activities throughout the week on my own. My friend and I each had a few things we were interested in that the other didn’t want to do, so this helped each of us have the experiences we were looking forward to.
Plan similar arrival/departure times. We were able to book departing flights around the same time meaning we could split the cost of a taxi to the airport and have some extra time to hang out while waiting for our flights. Of course, you can’t control airline schedule changes, so our best-laid plans of arriving within an hour of each other were foiled and I grabbed a cocktail by the pool while waiting for my friend to arrive. (No complaints there.)
Keep communicating. Throughout the trip, we continually asked each other how we were feeling and what we wanted to do next. It helped reinforce the expectations that we set before the trip as well as provide space for some things we didn’t discuss in advance, like what to do at midnight on my birthday.
In the end, I had a really fun experience traveling with this friend. Does that mean I’m signing off on solo travel? Absolutely not. And I’m still going to be picky about who I travel with and what kind of trips I do with other people. But this trip was a good reminder that even the most seasoned solo traveler can (temporarily) change her stripes.