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Hiking from Cusco to Machu Picchu, Peru with JUMP Adventures


Hikers in Oboz footwear summit a long trail in Peru.

In May of 2025, Traveling Jackie, Oboz Footwear, and Osprey Packs hosted a massive giveaway to award one lucky winner a spot on Jackie's group trip to Peru this fall. Oboz and Osprey also provided gear for participants of the trip, and in September of 2025…


Fourteen of us (including our lucky trip winner) set out from Cusco, hiking for 9 days all the way into Machu Picchu via the sacred Inca Sun Gate. 

A group of hikers crosses a bridge through a canyon in Peru


On the outside, it looked like walking along many Inca trails through ancient archaeological sites in the Sacred Valley, over multiple 14k'+ mountain passes, overcoming daily challenges together and spending our nights relaxing and reflecting in local mountain lodges. 

A group of hikers on bikes during a hiking trip in Peru in front of a church


On the inside, as with any adventure travel experience, it wasn't the iconic sites that made this trip for us — it was the in-between moments, the laughter, the tears, the digging deep, the strength and camaraderie of the group, as well as our individual willingness to show up and do hard things that truly made this trip memorable and life-changing. Perú set a beautiful stage for such an impactful part in all of our stories.

Here are some glimpses into the experiences we had along the way!

 


Choclo con queso

To ease into our demanding hiking schedule, we started with a 5-mile loop out of Cusco and all the way back through the streets to our hotel, cutting through the Sacsaywaman archeological site. With heads down, focusing on putting one foot after another and keeping our heart rates calm (as we were still adjusting to being over 11,000 feet), we didn’t expect the surprise visit (and delivery!) from our driver. 

Hikers in Oboz footwear summit a long trail in Peru.


He pulled up on the side of the road and proceeded to serve us all ears of giant corn and massive chunks of cheese. No utensils; just eat-like-an-apple-style chunks of cheese. Insert mouth-watering. This savory snack was new to me, perfectly paired with a hot hike, and now I wish I could have it every day. If you’ve ever had the privilege of tasting giant Peruvian corn, you know. This snack proved to be just the beginning of the endlessly lavish meals and delicious flavors of Peruvian cuisine that we got to explore throughout our adventure.

A hiker holds a corn snack during a hiking trip.

 


Not one, not two, but THREE 14ers

Admittedly, none of us quite realized we’d be hiking up to and over 14,000 feet - ahem, not once, but THREE times, in just four days! (#Peru) The mental and physical challenge this presents is NOT small! But we each embraced the invitation and stuck together, finding that even when words (and breath) escaped us at such high altitudes, the collective momentum and energy of the group kept us moving, together, slowly but surely, towards our goal. And we celebrated every single summit like the accomplishment that it was, eventually hiking 50 miles in, around, and through the Sacred Valley and surrounding mountains all the way to Machu Picchu.

Oboz footwear hikers on a trail through Peru


Pro tip: Carry Snickers bars and reward yourself with them on top of mountains whenever possible. 

Two hikers on a backpacking trip eating a snickers.


No dancing in Machu Picchu

We might be that group that sings and dances our way through ancient archeological sites, because what is life without a little fun?! So, when we arrived at Machu Picchu from above (after a week of solid hiking) we spent some time enjoying the view and taking photos as a group.

A view in Peru at Machu Picchu


And then, naturally, we started to have a mini dance party to celebrate our accomplishment. No one noticed our guide shy away from us as if he didn’t know us - he simply didn’t want to spoil our moment! - and then suddenly a whistle sounded and a voice started yelling at us to stop. Apparently, you are not allowed to dance in Machu Picchu. Okayyyyy. That one was definitely a buzz kill, especially since I hit the wrong button on my camera and was NOT, in fact, videoing our shenanigans as I thought I was. Oh well, I guess now there is no incriminating evidence. Evi-dance? Okay, I’m done. 

Stairs at Machu Picchu


The REAL highlight of the trip

One of the magical things we do on my trips is share, all throughout the trip, our highlights, lowlights, and what we are learning (we call this Rose, Bud, Thorn). At the end of each trip, I invite participants to share their overall roses (highlights), and ten times out of ten, this is what happens: 

Two explorers on bikes wearing Oboz footwear


Although the iconic sites (i.e. Machu Picchu) are what took up space on people’s bucket lists and landed them a spot on this trip, their biggest takeaways have nothing to do with what we saw. The takeaways are what was felt on those hard days when we pushed ourselves to our limits and then were rewarded with hot meals and campfires and glasses of wine under the stars.

A group on canoes during a backpacking trip through Peru


They're what was shared in those in-between moments, like when we actually did dance among the ruins and “Om" into the niches, when we were so tired after our third 14er only to arrive at our gorgeous mountain lodge to sit in private hot tubs and watch as a rainbow stretched across the sky. The powerful memories and lessons are in the bonding between people who showed up as strangers, individually, to do the same hard things, and left as part of a collective story, rewarded with accomplishment and new perspectives and measurements of their belief in their own strengths and capabilities.

Two hikers in Oboz footwear embrace after hiking to Machu Picchu


Adventure is the invitation, the destination is the stage, and YOU are the one who gets to determine your story. That is the power of choosing to show up, and discovering the real, unique-to-you highlights of travel for yourself, and knowing that no matter what happens, no one can ever take them away from you.

A hiker in front of expansive Peru views and rocky mountains


Here's to choosing to show up and say yes to the invitation of adventure! However big or small that may be. 

A hiking group wearing Oboz footwear after a big day on the trail heading to Machu Picchu