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How to Approach Vacation Planning for Maximum Enjoyment

It’s not so much where you go, as how you go.

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Let me know if this sounds familiar: I need a vacation, you say to yourself, likely over dinner after a long day at work. You feel energized by the idea and you start Googling flight prices. You probably stop and start this process several times, cowed by the cost. You start making mental calculations. I’ll only be able to be there for five full days. I’m going to blow all my savings. Is it really worth it? Finally, even more burnt out than before, you decide that screw it, you need this, and you go ahead and book your trip.

But your excitement only lasts for a day or two, maybe a week at most. Then, more anxieties start to creep their way into your consciousness. Can I afford the time off work? Why am I spending on this when I should be saving money? What’s the point of going away anyway, I’ll just have work when I come home to catch up on? And now that you mention it, where, exactly, is my suitcase?

Before you know it, your vacation isn’t feeling like a vacation at all—because your so-called relief from the turmoil of daily life has started to look unnervingly like turmoil itself. And so for many of us, the idea of travel that’s truly relaxing feels like an elusive myth that we’re chasing without success. Or even worse, it feels like a waste of time.

But it doesn’t have to be this way. As a travel writer (and host of the Webby Award-nominated Armchair Explorer podcast), I’ve been lucky to go on a lot of trips. I’ve trekked with Shugendo Monks in Japan, spotted giant condors in the Peruvian Andes, taken part in indigenous medicine ceremonies in Monument Valley, and dragged my kids on dozens of family road trips. Some of which have even gone smoothly.

And though even the most idyllic trip has its ups and downs (ever needed to pee in the middle of the night while camping on the side of a cliff?), the most memorable things in life always do. What my life of travel has taught me is that it’s not so much where we go, as how we go.

At the end of every episode of Armchair Explorer, I say “the more we look for wonder in the world, the more the wonder of the world becomes a part of who we are.” For me, that’s what travel’s all about. It can lift us out of the stress of our day-to-day lives, and show us glimpses of beauty, awe, and adventure that we’ll remember forever. Travel inspires us to live our lives to the fullest.

It’s crucial for our well-being too. Studies have shown travel can boost confidence, improve health, and give us perspective on our lives back home, helping to answer difficult questions and pick our path forward with more clarity.

So, forget about the stress and the to-do lists, for now. Instead, just dream. I’ve compiled this collection of everything from inspirational podcasts (some of them featuring yours truly) to informative articles, practical tips, and even a hilariously heartwarming short film that I guarantee will give you the itch to hit the road.

So go ahead, pop on your favorite playlist, pour yourself something to drink, and get ready to get out there.

Image by Anastasiia Shavshyna / Getty Images

Why Travel Should Be Considered an Essential Human Activity

Eric Weiner
National Geographic

“Start here. This is a great jumping off point for your travel journey—a piece that will stir up your enthusiasm and get you in the zone for travel planning and research. In the grind of our daily routines, it’s easy to get lost in the minutiae of responsibilities and forget that sometimes, the best thing we can possibly do is leave it all behind. This gave me some great perspective, not only on human history and psychology, but on a new way to look at travel—not as a given, but as a gift.” -Aaron Millar

Land of Wonder: Four Weeks on Colombia's Magdalena River with Jordan Salama [LISTEN]

Armchair Explorer
The Podglomerate

AM: “Jordan Salama is a young travel writer who embodies the art of mindful and intentional travel. In this episode, which was a delight to record, he recounts his journey traveling the length of the Magdalena River in Colombia. For me, the highlights of his story were all the people he met along the way—from the biblioburro (the donkey bookseller) to the silversmiths and jewelry-makers living in a real-life Macondo.”

The Art of Being a Flâneur

Stephanie Rosenbloom
The New York Times

AM: “I interviewed legendary travel writer Rolf Potts for my podcast, and he told me that the best way to travel is ‘to dare to be lonely, lost, and bored.’ This NYT piece perfectly captures the value of this approach to travel— not going in with a rigid agenda, merely letting your interest and your surroundings be your guide. Hint: It makes for a much richer, deeper experience.”

Solo Travel, According to Rachel Cargle [LISTEN]

Women Who Travel

AM: “One of the most accessible ways to travel is by taking a solo trip—whether that’s a long weekend nearby or a month-long jaunt abroad. But solo travel can feel daunting, especially if you haven’t done it before. I love that this episode breaks down the pros, cons, and how-tos of solo travel. It’s something that I think we should all make an effort to do at least once, so maybe this episode is your sign to book that flight.”

The Travel Green List


AM: “Wanderlust is one of my all-time favorite magazines for off-the-beaten-track travel advice and practical recommendations. And with their Travel Green List, they’ve taken their recommendations to a new level. Wherever you want to travel in the world, whatever type of vacation you want to have, this thoroughly researched guide will help you plan your perfect trip to be guilt-free and as enjoyable as possible.”

Central Nature Trail [LISTEN]

Hidden Trails of Oregon

AM: “This trip to Oregon was unforgettable for so many reasons, but all of my favorite experiences there happened outdoors. For me, spending time in nature is one of the most important things for well-being, so combining that love of nature with travel is about as meaningful as it gets. We recorded this one on location, so listen in to hear what it sounds like when you reach the top of Watchman’s Peak and see Crater Lake for the first time. Spoiler alert: there’s a lot of screaming.”

The Rewilded English Farm Where ‘miracles’ of Nature Happen

Elizabeth Fitt

AM: “I’m a huge fan of Positive News’s mission, and this dreamy little piece captures it beautifully. It’s a great example of how doing what’s best for nature can also be what’s right for tourism and the local economy, and how you can actually use your tourism dollars to make a difference.”

Aaron Millar

Aaron Millar is an award-winning British travel writer, podcast host, and travel aficionado. A regular contributor to the Times of London, National Geographic Traveller, The Guardian, and more, Aaron’s passion is telling travel stories that inspire people to explore the world, celebrate the outdoors, and live life to the fullest. His podcasts have been nominated for two Webby Awards, and Aaron has twice been named Travel Writer of the Year by the British Guild of Travel Writers. He’s trekked with Shugendo monks in Japan, descended into a volcano in Iceland, camped while hanging from the cliffs of the Colorado Rockies, and staggered through a 100 mile pub crawl in the UK, among many other stories around the world.

Now, Aaron serves as the host of Armchair Explorer, a leading travel podcast, and he’s the founder of Armchair Productions, the audio experts for the travel industry.