Planning My First Solo Trip

Most of my life, I traveled with family, which is really nice when you’re a kid that doesn’t have to pay for anything. Now that my sisters and I are all adults living in different states and paying our own way, we prefer to travel with friends and significant others, because we are also very different in our vacation styles (typically mom & I want to get out and explore, while my sisters are content to lay by the pool with a book).

Having few friends and no significant other myself, most of my travel involves visiting those few friends, or my family. But that involves staying at someone’s house for the weekend and maybe going out to brunch. It’s not really a vacation. Not a destination.

If you know me, you know I’m a Disney Adult, and I like to spend my birthday in Disneyland. I do have some close friends who love Disney as much as I do, but they have family, friends, and responsibilities that understandably don’t make it feasible to take a Disney vacation with me every year. I also have friends who don’t love Disney as much as I do (but they love me!), and Disney is too expensive a trip for someone who doesn’t really want to be there. (Also, I’m trying to rope-drop to close, 30k steps minimum, and my companions need to be on board).

In my search for adult friendships, I started a small group a few years ago. Originally a weekly bible study, it’s now grown into a community of women who also meet to set and reflect on their goals, watch movies, read books, and truly do life together. If you’re a millennial woman interested in joining this community, please reach out on my contact page!

We toyed with the idea of a travel component of the group for a while, but I spent too many hours creating surveys only to get results like: Plan a 21 day trip to New Zealand for $1000 per person (lol) with active activities for half the group and relaxing activities for the other half. Since the group is virtual, the members live all over the world, which was an additional issue when it came to trying to coordinate a trip.

Enter the problems that prompt many people to solo travel:

  • Difficulty working with multiple budgets and schedules

  • People not valuing the same things (one will spend more on a flight but less on a hotel, etc.)

  • Clashing personalities (who will room with who and how do we decide?)

I started following a bunch of solo travel influencers to convince myself that I, too, could do this.

The thing is, I’m directionally challenged, and I’m scared of taking the wrong train somewhere and spending the rest of my life wandering a foreign country, never to be found (dramatic, I know, this is me you’re talking to).

So I didn’t really want to travel internationally by myself.

As much as I love Disney (I’ve been to Disneyland, Disney World, Disney Aulani, and on Disney Cruise Line and love them allll), Disney is built for families. The idea of going on a Disney vacation and looking around at all the families when I couldn’t get a single person to go with me just feels… depressing.

A cruise seemed to solve a lot of these fears. Sure, you can get lost on the ship, but there’s only so far you can go. You’ll get there eventually. It’s international. There may be lots of families around but there are brands that are more or less family-focused. There are tons of activities so if you want to do something from the minute your eyes open to the minute they close, you can, and if not, you can lay by the pool or in your room or in a random lounge chair, or do whatever you want!

I found a solo travel influencer booking on Virgin Voyages, which is an adult-only cruise line that also offers events and activities for solo-travelers, and after some research, that seemed like the best fit for me. I’ll tell you all about the trip in my next post!

If you’re thinking about booking a solo trip but fear is holding you back, starting with these may help prepare you:

  • Go to the movies alone

  • Go out to eat by yourself (at a sit down restaurant, not fast casual)

  • Go to a concert by yourself (you can sit as close as your budget allows and may even make a friend!)

I booked my trip a year out so I had time to do all of these baby steps. I go to the movies by myself all the time, but the other two I had to work up to and they ended up being a lot of fun!

Check back next week to read about the cruise ❤️

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Solo Sailing on Virgin Voyages’ Brilliant Lady

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STL Staycation: A Week with My Sister