How to Make Your Dream Trip Happen

Use your head to start checking adventures off your list.
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Use your head to start checking adventures off your list.
live your life

Photo by Patrick Heagney

Rainier, Grand Canyon, Patagonia, New Zealand. Sound like your bucket list? We all have one, but for some, it never changes. Nothing comes off. Can’t go this year, you say. No time, you say. Not enough money. Not confident you can even do such a big trip, anyway. All excuses, and all solvable with your big brain. We’ll show you how here. Because the world is calling and it’s time to answer.

Family. Work. Chores. These obligations are real, and they will steal every weekend and vacation if you let them. Don’t. Adopt a strategy that enables you to maximize free time. Follow this planning advice and learn from three masters of getting out more.

Get sponsored

Convince someone else to fund your expedition with these eight grants for adventurers.

Do the math

If you start with a dream trip—say, trekking to Everest Base Camp—that takes longer than you can manage, you’re just setting yourself up for “not having enough time.” Instead, first calculate how much time you can feasibly take off using these steps:

(1) Your job How many consecutive days can you take off? Write that number down.

(2) Your family Are they coming with you or doing without you? Either way, determine the maximum number of days you can be away. Write that number down. 

(3) Other obligations (pets, volunteering, other time sucks) Think about which you can’t get out of and which can be covered. How many days can you get away? Write that number down.

Circle the smallest number. This is how many days your life list can handle. If you only have five days, then the John Muir Trail is going to have to wait; floating Canyonlands, however, is totally possible.

Match a trip to your schedule. Put it on the calendar.

+50%

You’ll be that much more likely to accomplish your goal just by writing it down, reveals recent research from California’s Dominican University. Even more effective? Telling others. Folks who wrote down their ambitions and had a friend or family member hold them accountable were the most likely to achieve their goals.

Take a lesson

These three readers don’t possess supernatural powers—they use the time they have to accomplish their hiking goals.

The Corporate Exec

Paul Andrews, 48, Louisville, CO

Hiking goal:Bag all of Colorado’s Centennial Peaks in three years

The key to navigating a demanding job? Pick a goal you can accomplish on weekends, says Andrews, a partner and CFO for a real estate investment firm in Denver. Andrews, who’s trying to climb Colorado’s 100 tallest peaks in three summers, knocks them out in four- and five-mountain chunks each weekend with one week-long epic each summer. Also helpful: Andrews has an empty nest, so he only had to get his wife on board. “She understands that, even if she doesn’t come, this is what I’m up to on weekends,” he says. Midweek, he wakes up early to swim, cycle, or hike his backyard mountains: “This goal keeps me motivated year-round,” he says.

The Busy Mom

Jen Lumanlan, 36, Berkeley, CA

Hiking goal: Tackle France’s 170-kilometer Tour du Mont Blanc 

Having an 8-month-old kid is a full-time job that you can’t just walk away from, so for most mama bears, trekking the 100-plus-mile Tour du Mont Blanc would be soundly out the window. Not Lumanlan, who took her daughter Carys with her. “While I was pregnant, I was thinking, Am I really done?” Lumanlan says. Convinced that she wasn’t, she planned the trek before Carys was even born. She recommends finding a route both with plenty of bailout options and huts—like linking Colorado’s 10th Mountain Division huts, which Lumanlan has also done with Carys in tow. “It’s become something we’ve really bonded over,” she says.

The Millennial

Joanna Sweetgall, 29, Wayland, MA

Hiking goal: Check out all of the West’s classic climbing destinations 

Even if your goals don’t mesh with a 9-to-5, they don’t have to derail your future. After graduating from college, Sweetgall jumped into a career as a research engineer. She made industry connections, built her résumé, earned promotions, and—after six years—left. “If I didn’t go for it, I’d look back in 10 years and regret it,” she says. The key is timing: Go before you’ve settled down, but after you’ve had some career success, so you’ll be in a “prime, hireable state” when you return. “I thought I’d get a lot of You’re ruining your life, from senior-level people,” Sweetgall says, “but what I actually got was I wish I had done something like that.”

Bonus: Score free grub

On long hikes, you almost always run a calorie deficit. Save a few bucks and boost morale by thinking with your stomach.

Trail angels

Enjoy everything from seemingly random trailside snacks to home-cooked dinner. It’s hard to bank on trail magic, which will make you all the more appreciative when you stumble upon a beer-filled cooler.

Other Hikers

Pinpoint weekend warriors and dayhikers for your best chance at beef jerky and fresh fruit and veggies. Spark a conversation and casually mention how far you’ve come and how tired and hungry you are (try not to come off as a bum). Since weekenders often overpack anyway, chances are good you’ll land some freebies.

Hiker boxes

Don’t be picky when perusing the leftover supplies that other hikers have discarded. Instant mac-and-cheese with a side of creamed asparagus never tasted so good.

Restaurants

Spiffy up before walking in, then ask the restaurant staff if they have any hiker specials (works best in trail towns). Some offer a scoop of ice cream or a slice of pizza, while others may even supply a full meal if you look grateful—or hungry—enough. (Don’t beg or ask to eat other diners’ leftovers, though, you dirtbag.) —Jonathan Olivier