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How We Work Together To Plan Our Travels

Relationships are a funny thing. You start out as two independent souls—each with your own way of doing things. Then over time you become a team, a perfect one-two punch, if you will, that when united is a stronger force than anything you could’ve imagined when you were single. Like a lot of guys, I resisted this notion at first: I don’t want to be BRANDY (Beth + Randy, get it?), I’m Randy dammit.


Things changed for me, though, when we started traveling together. First, Beth introduced me to the gorgeous frontier beyond Tijuana in Baja, Mexico, then Guatemala and Oaxaca, and finally the world. We were together 24/7. We faced unpredictable circumstances. And along the way we fell more in love. Recently, I was reflecting on this, and I realized that how we plan and prepare for our trips is just as important as how we work together on the road. So, I thought I’d share with you a few of the ways we come together to plan our travels, be it a cruise through the Caribbean or a backpacking adventure in Guatemala.

Related: 5 Awesome Tips to Help You Travel Better


Like most travelers, Beth and I have a thing for guidebooks and maps. Before smartphones and blogs, we’d spend weekend afternoons at a cocktail lounge near our house in San Diego. We would sprawl out our guidebooks and maps across a booth and settle in with our drinks. These days we do most of our planning online. And when we start to plan, we each have different roles in the process. It’s kind of strange, really. We never actually defined these roles, they just happened organically over the course of our nine years of traveling together.

Beth is the dreamer of our little duo. While girls her age grew up planning their wedding days, Beth spent her time dreaming about places near and afar. She caught the travel bug from her father, Bob, who used to take the family on epic road trips into the American West. She’s also a dynamo for finding killer apartment rentals, as evidenced by her recent scores in Venice and Florence, as well as cheap airfares like the $400 round-trip tickets we got for our Italy trip in May. So then, what do you do Randy? Well, I handle the logistics, you know transportation stuff, setting up an overnight stay here or there, and I’m also the Debbie-downer who has to keep the dreamer in check. No Beth, I’m sorry. As much as I’d love to go to Lapland to see the Northern Lights, it’s just not really possible in less than 12 hours from Helsinki. In other words, we balance one another out marvelously.

This balance also extends to planning out what we want to see, do, and eat on our trip. Normally, we keep our itinerary pretty light to leave room for spontaneity. But there are often several key things one or both of us would like to see in any given destination. So whoever has the most interest in the place will research a few must-sees before the trip. More often than not, we get a lot of our information online from travel magazines and blogs. When we have time, however, we also like to go to the library and scour the travel stacks for books about where we’re going. This gives us the chance to get back to our roots of spreading everything out on a table and diving into a destination together; except now, we have to mix our own cocktails.


I hate to admit it, but when it comes to packing, Beth trumps me; she’s got a Tetris-mind. At this point, we’ve got the packing thing down to a science. But amazingly we do have times where we don’t see eye to eye. It usually happens when I decide I’m going to go hyper light and try to take the smallest bag possible. Sometimes it works. For example, on our seven-day Carnival cruise last November, I went super light, opting to carry the Tom Bihn Super Ego, essentially a large messenger bag, and it was perfect. Mostly, though, I fail and end up switching to a larger bag.


After our luggage is packed, that only leaves our bathroom stuff and electronic gear. Beth takes the former and I the latter. Again, this was another unspoken thing; it just evolved that way. Once those things are good to go, then it’s time for our final task: the checklist. This is all Beth. It’s something I’d probably never do on my own, but I do really appreciate it. With the checklist in hand, we’ll go through and make sure we’ve got everything we need. Ironically, on our recent trip to Italy, we switched up our luggage situation and didn’t do a checklist, and guess what happened? Yep, you guessed it; we forgot a number of things. Doh!

All The Small Things

In a perfect world, we’d plan, we’d pack, and then we would jet off on our holiday. But, as I’m sure you know, we don’t live in a perfect world and there are always loose ends to tie up before we leave. Like most people, Beth and I are working right up until our departure time. In addition to Beers and Beans, we run two other businesses: Pin-Up Live! and Speakeasy Travel Supply. This is where Beth’s affinity for the checklist comes in handy, again. She draws it up a few days before our trip, and then we go through it one item after the next to ensure we have our metaphorical house in order before the trip.  Without a doubt, this is the least fun part of preparing for a trip. Ironically, though, it’s the most liberating part of our pre-trip preparations; I liken it to being prepared for an exam in school. I always hated studying…cramming…for the test, but the feeling of ease I had when I sat at my desk to take the exam made it all worthwhile. Beth and I get that same easy, lucky, free feeling when we take our seats on the plane (or bus, train, ferry, cruise ship, etc.) and know the only thing we have to think about is where we are going, not what we left behind.

This post was created for Away We Go with Carnival, the destination for getting in the getaway state of mind.