How to Travel with Your Partner: Round III

If at first you don’t succeed, try, try again.

The Chief and I have been lucky in love. Vacation, on the other hand, has been a beast.

Alaskan Malamute puppy

From arguing our way through Ecuador to falling prey to a flu (oh, and also to arguing) in Mexico, our last two vacations have left a lot to be desired. So, after two years of being cooped up in a cabin in the woods (we jumped the gun on 2020 and deemed 2019 our Year to Stay at Home. Little did we know…), we found ourselves planning vacation number three. Third time is a charm, no?

Now, right off the bat, let me address the elephant quietly plodding about the room: Julia, you’re complaining about vacation?! No, no, no. Bear with me a moment.

Growing up, vacationing was eaaassssssy. Right? I mean, typical traveling bumps and bruises aside, the most I had to do was show up (and as I grew up, also quell my snarky ‘tude). Plans were slowly made each day as the sun rose, meals were paid for, lodging decided months ahead by a travel agent (oh yeah, we old school). As a young’n, I was lucky enough to go to Mexico annually and I looked forward to next year’s adventure the second we returned to California.

Still, as I grew older, the intricacies of vacation showed their true colors. From budgeting and booking tickets (on our own! Eeek!) to combining different needs and personalities into one adventure, vacation turned out to be a little more nuanced when I peered behind the curtain of adulthood. So, as I started traveling on my own in my late teens, it took a moment but then…I found my rhythm.

My rhythm.

Julia Chester
Meh, I’m gonna do my own thing.

Me, myself and I. No one else to plan around. No quirks to consider. No debates about where to go and what to do. Just me.

Enter: coupledom, also known as: I take your needs into consideration and you take my needs into consideration, considerately.


Mmmmm…not always. While The Chief and I came together like magnets in an instantaneous, easy attraction, that smooth sailing of a start certainly hasn’t meant calm seas for life. You’ll be surprised to know (I kid, I kid) that we are both stubborn, hard-headed individuals. Who would have thunk a dude living solo in the woods for 15 years meeting a woman hell-bent on reconnecting with her 20-something solo traveler self would butt heads?! These buttheads would!

Young love
Brand new love

Truth be told, The Chief and I did have an immediate connection. If there had been water between us, I’m pretty sure it would have parted to make way. I faintly recollect the clouds opening and angels singing, or at a minimum the sun shone a bit brighter and the birdsong grew louder, at least to me. It was an easy, instant love. And thank goodness for that because in times when the angels are off-key and the sunshine is nowhere to be found, it’s helpful to remember that at one time, all was easy. I hold that memory in my back pocket for the rougher times. Like vacation.

Vacation, Julia? Realllllly?!

Quito, Ecuador
Taking a break from being grumpy to laugh at the fact that I accidentally flashed everyone below us on an unanticipated ladder adventure into the church’s bell tower. Whoops!

I know. I know it sounds ridiculous, maybe even a little sadistic. I mean, who can manage to cultivate a bad vacation? It turns out, a lot of us. In talking to friends, family, professionals and a few Google searches, I’ve learned that vacation isn’t always the land of insta-worthy moments. Vacation, to me, means a new place, often unexplored. It means taking me out of my comfort zone, out of all that I know and introducing me to new foods, new sights, new people, new customs. It’s a whole new world (cue the music, Aladdin). Still, as I’ve aged, somehow I think I’ll be able to control the experience in this new world, despite never having grasped the ability to do so in my own world (hint: it’s impossible, that’s why). The Chief, on the other hand, likes to leave things open and free, sort of.

So, as we approached our Vacation Number III, I found myself falling into the traps I’d laid for myself. This would be the perfect vacation, right? Oops! Trap number one: Perfection. Fooled by the sneaky Jujubee once again. I resigned myself to researching the heck out of Hawaii, only to realize that I had been confusing my memories of the Big Island with my memories of Maui as I planned, er, I mean researched. Trap number two: planning. OK, so it wouldn’t be the land of sandy beaches I had thought but it was going to be perfect. Whoops! Trapped again. I talked myself off of the planning perfection ledge a few times while The Chief told me it would all be fine and we should just see where the wind takes us.

Rome, Italy
Me, in my 20’s going where the wind took me (and thus, missing my train)


Banjos, Ecuador
Go with the wind. Instead of feeling freeing, it felt more like this!

Trap number three: thinking you’re the person you were in your 20’s whilst securely seated in decades beyond.

Both of us traveled extensively in our late teens, early 20’s and many times we did so alone. We loved it. No one to answer to, no path to follow, just instinct and…the wind. Now, in our 30’s and 40’s we both love to follow the wind but we also like to know where we will be sleeping that night more than an hour before our heads hit the pillow. So, what did we do? We ignored this truth we’ve learned about ourselves and left the vacation up to the wind.

After crazy (read: difficult, not unnecessary) COVID hoops to jump through and a 15-hour travel day, we finally arrived at our destination. Two hours later, we were settled into our slightly funkier than we had realized room but it didn’t matter (well, maybe a little). Our skin was brighter, our hearts were lighter, we were in Hawaii! Just as we put our bags down, my girlfriend, also on the Big Island, called. “Where you at, boo boo?!” I had researched where we The Chief and I would go for dinner while he had picked up the rental car. I told my girlfriend our plans and it turned out that she was headed to that exact restaurant right then! The wind! It had taken us in the right direction. The night ended with drinks and dinner with best buds and toes in the sand. We fell asleep warm and happy. Success.

Lava Lava Beach Club
Warm nights, I love you.

Day Two took us driving toward Volcano where we’d stay for two nights in a sweet little cabin in the woods (sound familiar?). As we parted ways with the sunny Kona coast, I could feel my chest tighten a little. After two years in Alaska (3/4 of which I’m pretty sure has been Winter), I had felt myself open and then close like a Morning Glory in the setting sun.

Into the dark again

I desperately needed more sunshine. I felt panicked. Still, we were headed towards adventure and The Chief’s birthday. A little rain couldn’t be so bad, right? The day was beautiful, albeit increasingly overcast as we made our way along the coast. After many a roadside detour for poke, we found our home away from home. It was…

not perfect.

Volcano, Hawaii
Cute but…

Dark, damp and cold with firewood that wouldn’t catch, my heart started beating out of my chest. It was such a visceral reaction that, against my better judgement, the words just flew out: “I’ve gotta get out of here, babe.” Commence arguing for Vacation Number Three in three, two, one…

Despite doing his damndest to appear unflappable in the face of essentially showing back up in Alaska (scratch that, it was COLDER in this house than ours in Alaska), The Chief eventually admitted that he too wanted to bail. So, after a few hours of debate, we did. Not without seeing the awesomeness that is the Kileaua Cauldron and Mauna Loa. Then, we bailed and headed back to the sun.

Chris Chester
Steamy (See what I did there?)!

Our fly by the seat of the pants, go with the flow approach wasn’t really working and neither was staying in a different place each night. We decided we weren’t up for another Airbnb surprise and booked the rest of our time, a week, in a condo in resort-land which is not normally our style but you know what? It was amazing.

Waikaloa Village
Sunset moonrise

And you know what else? Once we did that, the flow returned, the wind blew us about and damned if we didn’t sail on it like two relatively unfettered feathers. Sure, there were a few little hurdles but overall, I think we’ve broken the vacation curse (knock on wood, I know) because for the first time in our time together, we had a wonderful vacation. From adventuring through beautiful valleys and getting accosted by “wild” horses, to saving some stranded (what turned out to be) Alaskans, to getting to see my Mom and her beau who just happened to be in Hawaii too to sipping Mai Tais in Chaise lounges IN the pool, it was amazing.

Hilo, Hawaii
Swimming with A
Polulu Valley

Amazing. Finally.

On our last night, eating at our favorite restaurant, we met a new friend. We talked about the epic waves that day (hello, Red Flag warning!) and everything from his life on the island to politics to love. As we finished up, he remarked: “Isn’t it beautiful the things you encounter when you go where the wind takes you? Like tonight? We all followed our intuitions and it lead us here, together.” I couldn’t agree more.

Finally, we had learned to let go while simultaneously learning that in order to be in the flow, we both needed a few things in place, like lodging. Really, that was about it. Oh, and some staples in the refrigerator. Life is a little different for both of us since our solo traveling days of decades past but we find those old selves when we nurture the needs of age and lifestyle. Our daily life is hard enough. From hauling water to traveling 8 hours for epic supply runs, life out here is rewarding but damn is it tough sometimes. Vacation shouldn’t be. This time, it finally wasn’t.

With love,

from Alaska


P.S. Do you have any vacations on the horizon? What are your tips or tricks to keep your vacation on the happy train?


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