The first rule of adventure travel? There are no rules to adventure travel. Throw them right out the damned window. And now that we’re getting comfortable with the onset of fall and the concept that eventually, winter will come, we have our work cut out for us. What’s the next adventure that’ll get us out from under this pile of paperwork and into the brisk or frosty air? And who’s going to have the experience to get us there?

Justin Wood knows a thing or two about frigid, rarified air and what it takes to breathe it. The 39-year-old operations manager for REI Adventures is an 11-year veteran of the travel company—which is this year celebrating its 30-year anniversary—and he just scored some major brownie points by summiting Mt. Kilimanjaro, a personal first and one of the many offerings his team has made available to adventurous travelers just like you and me. “It was everything I dreamed it would be and more,” Wood tells RealClearLife. Even though it was an unusually blustery, cold day, Wood says it was crystal clear way up in the heavens. And in true climbing-pro fashion, he high-fived his fellow trekkers, snapped a couple of photos, and immediately started his descent. Been there, done that. Adventure travel is as much about keeping moving as anything.

Wood got his start in the industry teaching rock climbing and tells RCLife that although he grew up in the Midwest, he was exposed to travel at an early age, his father packing the family into the car and going on exciting Westward jaunts. “I’m sure it was those experiences that made me think, ‘Why would I want to work when I can do this instead?’”

Over the years, that has worked its way out into a strong set of principles on what adventure travel entails to the career specialist. “Every individual has a different idea of what an adventure is,” says Wood, “[but] because we’re REI and the co-op was founded on active human outdoor adventure, we can focus our energy more on those kinds of ideas.” Or as he puts it, “human-powered exploration,” which is everything from gritty backpacking to backcountry camping and kayaking.

REI Adventures’ Wood while on the hike across the Shira Plateau on his way up Mt. Kilimanjaro (REI Adventures/Justin Wood)

Of course, if you happen to be looking for an adventure attuned to the quickly approaching fall or winter months, there are some factors you must take into consideration. “I think with fall and winter adventures, you have to go into it with a spirit of flexibility,” explains Wood. “You might plan a trip in December at Yosemite thinking you’re going to go snowshoeing, and you might be hiking instead,” he continues. To that end, Wood lives by the following mantra, which we strongly urge you to memorize: “There is no bad weather, only bad gear.” In short, if you pack all the proper accoutrement—tent, temperature-rated sleeping bags, waterproof shells, hiking boots, socks, gloves, sunglasses—then you’ll be right as rain, even if the rains come. “If you show up unprepared,” he warns, “it’s anybody’s guess.”

With that in mind, RealClearLife asked Wood to share with us a list of his top five fall/winter hikes, all of which are offered through REI Adventures. We discussed each trip in detail with him, so you can get an insider’s look at how the list came together and what you might expect if you want in on any of them.

Signature camping along the Mt. Kilimanjaro trail. (REI Adventures)

Africa – Mount Kilimanjaro Climb – Lemosho/Rongai Route

Look, we’re not going to lie; Mt. Kilimanjaro is a beast at 19,340 feet, and you’re going to need to be in spectacular shape to complete the 11-day hike and summit it like Wood did. To give you an idea of preparation, instead of going home, plopping on the couch, and watching Downton Abbey reruns, Wood would go on circuitous hikes on the way back from work in the Cascades Mountains and Foothills (he’s based right outside of Seattle). So if you don’t have a trusty mountain range on which to practice, we’d suggest finding one before you sign up.

However, the Kilimanjaro climb is more Wild than Cliffhanger; it’s a strenuous, uphill hike, not a ropes, carabiners, and crampons adventure. “You’re not having to navigate vertical rock,” explains Wood. (Phew, right?) But you’re not off scot free—as you get further up the hike, the air will get considerably thinner, and it’ll be more difficult to breathe, and therefore, an even more strenuous hike. “It’s hard to train for that,” Wood admits. “Those are conditions that you don’t encounter in too many places in the world.” In short, the daily mileage isn’t that big of a deal; it’s the elevation gain that gets you.

On the other side of that coin, though, the trek is nothing but breathtaking (no pun intended) scenery and a panoply of photo ops. That and REI Adventures offers potential mountaineers more than your average lap of luxury on the high peak. REI boasts that it is only active travel company to offer “signature camping” on Kilimanjaro. As Wood notes, it’s not so much high-altitude glamping as it is a more comfortable alternative to the usual. “You’re still out there, in a tent, in a sleeping bag, and camping,” he says, “but we’ve got people up off the ground on cots that are really comfortable with extra-thick sleeping pads, floor covering, tables, lighting, and enough of the extras that you really feel like you’re able to get comfy.”

It turns out that among REI’s spate of new adventure trips, they’ll soon be offering an alternate route up Mt. Kilimanjaro, known as the Rongai Route, which is 10 days long (versus 11) and also comes with the signature camping option. For Lemosho, the route that Wood took, you’re hiking across the Shira Plateau; while on Rongai, you’re climbing a northerly route under Mawenzi, the second of three volcanic cones that make up Kilimanjaro (Kibo is the third; Shira was flattened, hence the plateau). “You see a completely different face of Kilimanjaro,” explains Wood, of the new route.

Availability (Lemosho Route): Oct. 16–Jan. 3

Price: $5,600

Availability (Rongai Route): July 11–Sept. 13

Price: $5,000

Adventurers enjoying The Skogafoss waterfall on the Iceland Winter Adventure. (REI Adventures/Robert Hoetink)

Europe – Iceland – Winter Adventure

At this point, you’re already well aware of how hot Iceland is in the adventure travel space via Zicasso’s Game of Thrones tour. So it makes sense that Wood would include the island nation on his list, too. And while Thingvellir National Park, where scenes from Season 4 of Thrones was shot, is on his itinerary, this adventure couldn’t be more different than Zicasso’s.

One major way is that you’ll be doing a lot of it on snowshoes in the dead of winter. “If you really want to see Iceland in the wintertime, get out in snowshoes in the Blue Mountains, hit some backcountry hot springs, snowshoe out on the peninsula where you get out away from everybody, and you’ll see a totally different side of Iceland,” advises Wood.

Another day’s trek through Iceland along Solheimajokull Glacier. (REI Adventures/Ultima Thule)

Another great thing about this trip? You’ll be in warm, comfortable hotels or guesthouses each night, not ice caves like Jon Snow and Ygritte. Wood predicts daytime temperatures of about 30 degrees, so make sure to heed Wood’s advice and pack the right cold-weather gear.

Lastly, you won’t be left out to pasture on the subject of food, given that Icelanders eat traditional plates like horse, whale, puffin and fermented shark. “Iceland also has a tremendous contemporary food scene,” notes Wood, who did extensive research into the cuisine there before putting together the itinerary. He tells us you’ll be getting the best of both worlds.

Availability: Nov. 19–29

Price: $3,900

Machu Picchu (REI Adventures/KmCero)

Latin America – Peru – Machu Picchu Explorer

What would a top hikes list be without a nice dose of ancient history? REI Adventures offers a seven-day trek through Peru, three of which are spent at Machu Picchu. Some of the estimated one million tourists that visit the site annually opt to take a battery of vehicles up to the ancient Incan monument, while others take the long way, completing the strenuous hike, all the while barebones camping and smelling like a Grateful Dead show by the time they arrive. More power to them, right?

But as Wood explains, REI’s itinerary meets those options in the middle (don’t worry; you and Jerry Garcia will have nothing in common during the trip). “At Machu Picchu, you really take some time to absorb the place and explore it,” says Wood. “Too many people will go to Machu Picchu, spend a day there and go home.”

REI’s trip consists of a guided tour the afternoon you arrive, which includes that aforementioned history lesson; an entire day to explore the site for yourself and do mini-hikes within the area; and on the final day, a re-exploration of what you’ve just accomplished over the first two days, with maybe, a side-hike to the Gateway of the Sun tacked on. It’s all about immersion, says Wood.

Availability: Oct. 7–Dec. 8

Price: $3,700

Scenes from one of the Sedona hikes. (REI Adventures/Compass and Camera)

United States – Arizona – Sedona or Superstition Mountains

Adventure travel doesn’t always have to mean jetting off to some far-off land—it can be in your own backyard. So while it’s fine to rag on your weird uncle for never leaving the U.S., if he’s ruggedly enjoyed those purple mountains majesty, maybe you should hold your tongue.

Wood offered up two warm-weather options in the same state, so we figured we’d condense the two. Hell, if you want to, sign up for both of them.

The first one takes place in Sedona, a place we’ve been to and enjoyed—a spa-friendly oasis carved out of Arizona’s red-rock country. By no means a strenuous four days of hiking, REI’s Sedona adventure is all about enjoying the awe-inspiring scenery; taking in some of that Southwestern culture (such as the 1,000-year-old mining town of Jerome); and stopping to take a selfie next to another rock formation you’ll likely never get another chance to see in your lifetime (unless, of course, you double back).

The Superstition Mountains near Apache Junction, Arizona (REI Adventures/Bill Grove)

Superstition, on the other hand, is “your classic self-supported backcountry adventure,” notes Wood. Basically, you have your entire life in a backpack for a two-night adventure in the middle of nowhere under the stars with weird bugs buzzing hither and yon and coyotes howling all the while. You even have to … um … do your business in a self-dug hole—which we can proudly say we’ve done and is not the end of the world (here’s looking at you, Zion National Park). “One thing that everyone should have on their bucket-list in life is to poop in the woods,” says Wood, tongue firmly in cheek.

Availability (Sedona): Nov. 9-12

Price: $1,800

Availability (Superstition): Nov. 16-Dec. 3

Price: $800

A scene from the Doi Inthanon National Park hike on REI Adventures’ Thailand family adventure. (REI Adventures/Exotissimo Travel)

Family Travel – Southeast Asia – Thailand

To round out this list, if you pictured a trip to Thailand as something that falls short of a family adventure, you’re not alone. All we’ve heard about the place is cliff-diving this and James Bond Island that. With a lot of mixed drinks, clubs, and partying involved. Frankly, some of what you may have imagined would make a gentler person blush.

And while that reputation is there and intact, says Wood, both northern and southern Thailand offer surprisingly kid-friendly adventures, and he and his team have created what they believe to be the perfect itinerary with both parents and their mini-me’s in mind. “For children to go to Thailand and experience an ancient Buddhist kingdom with all of the temples, colors, cuisine, at a different pace of life, is a really fascinating experience,” he says.

This adventure, however, is not for the whiny, stroller-bound stick-in-the-muds, though. It involves quite a bit of being active, including hiking, biking, kayaking, and zip-lining. Not to mention the fact that you’ll get to visit an elephant sanctuary, where you’ll be tasked with bathing and feeding the giant animals—which made us think of Dirty Jobs more than vacation. No so, says Wood. “Elephant tourism in Thailand has been popular for a long time,” he explains. “For us, we have focused on visiting elephants in an environment where they’re being rescued and cared for.” (Not quite the Vetpaw experience, but you’ll likely hear stories from people who are sworn protectors of the giant beasts.)

Availability: Dec. 20–Jan. 1

Price: $3,000