Small-group adventures. Exotic locations.
Immersive experiences that connect you.
The people make
the place.
You've been meaning to take the trip. You just haven't found the right people to join you. That's what we're here for.
Groups of 8 | 3 and 5-day | From $3,000
What We Believe
"AI can plan a trip. It can't build you a tribe."
We bring together small groups of active, curious people who want more than a vacation. They want to surf with someone who cheers them on when they finally stand up. They want to share a meal with people who actually want to hear their story. They want to come home different, not mearly rested.
That's what ActiveLeading is: adventure travel that makes the other people in your group the experience. The destination is just the backdrop.
Who This Is For
You're probably not hard to find. You're someone who
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You have the desire, not the time...
...to research the flights, vet the accommodations, track down a surf instructor, and somehow also build a group worth traveling with.
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You have great friends...
...but none of them are still into this kind of adventure. Or they're scattered. Or life got in the way.
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You want more than a resort...
...You want to feel something. Challenge yourself. Connect deeply with others. Come back with a story worth telling.
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You know the difference...
...between a trip that filled your camera roll and a trip that actually changed how you see things.
If you read that list and nodded — you've found your people.
Why We Do This
When you hand someone money and a few days of your life, you want to some answers. Who is this person, and why does he do this?
When I was 10 years old, I used to walk up the street to my grandmother's house after school. We'd sit at her kitchen table, she'd make dinner, and we'd watch TV together. Most of the shows were beyond me (Seinfeld, Magnum P.I., Murder She Wrote), but one show lit something in me that never went out: The Young Indiana Jones Chronicles.
Every week, a young Indy was somewhere new (Egypt, the jungles of Southeast Asia, the middle of nowhere), getting into situations, meeting fascinating people, seeing things I couldn't imagine from a small town in western Washington. I felt alive just watching it. I knew, sitting at my grandma's table, that I would travel one day.
In college, I finally got my chance. My friend Tim and I flew to Beijing to visit Tyler, my former roommate who had moved abroad. We had almost no plan: meet up with Tyler, enjoy the city, each other, and the kind of fearlessness that only comes when you're young and slightly (mostly?) underprepared.
The Great Wall at Badaling, 2006. From left to right: our founder Jess Cisco, his friend Tim, and his friend Tyler. Halfway up a wall that was much steeper than we expected.
At the Great Wall, Tyler and I ran. We chased each other up the steps, jumped the parapets, played games across thousands of years of stone. Tim took his time, wandered, watched. Apparently, we got a lot of looks from other visitors who thought we were completely nuts, according to Tim. We didn't care. We were exactly where we'd always wanted to be: together, doing something that was only a dream a few year earlier.
That trip hooked me.
Years later, I've been to nearly 60 countries since then. And what I've learned, every time, is the same thing I figured out on those steps with Tyler and Tim: the destination is almost never what stays with you.
What stays is the shared experiences. The laughter. The moment you paddle past the surf break together and watch the sun go down. The conversation that started over dinner and was still going at midnight. The feeling of being around people who make you more yourself, not less.
That's what I'm building on every ActiveLeading experience. Not just a great trip. The feeling of being fully alive and fully connected — and the people who were there feeling it with you.
Who is this person, and why does he do this?
To share what travel offers
After visiting ~60 countries and knowing what matters--and what doesn't--Jess is passing it on.
To be a catalyst
Helping you step into the best version of yourself, Jess helps you never stop living. Adventure makes the step that much faster.
To feel it, too
Connection goes both ways. When your group paddles out together, Jess is there with you. That shared experience is the point.
What The Trip Actually Feels Like
Here are the moments that people tend to talk about for years afterward.
In the morning
Waking up to sunlight, instead of an alarm.
Seeing the ocean and hearing the waves as your first sights of the day.
Enjoying coffee with someone you barely knew 36 hours earlier.
On the water
For the first time, you stand up on a board. The whole group sees it. And someone you met yesterday is already cheering.
Over a sunset
Being present with no phones for 10 minutes. Just the group and the sunlight. Then, someone says something that opens a real conversation.
On the last night
Jess says something specific about each person at the table. You realize you've been seen.
What Past Adventurers Say
"During the long boat rides between dive sites, there was so much stillness. Nothing to do but sit, think, and talk to the people around you. In that stillness, I started to reflect deeply. I realized how much I value adventure. How much I care about our oceans. How much I want to live a full life - one where I’m not just chasing promotions or GPAs, but chasing moments that make me feel alive. Like watching sharks swirl around a bait trap during a dive. That moment didn’t care about my resume. It just was. And it took my breath away.
I had real conversations, laughed loudly, danced freely, and let myself be seen.
I had gone on this trip to get scuba certified. I came back a different version of myself."
~Tyler Hein, Bahamas Scuba Expedition
That's not an accident. We design for it. The conversations, the challenges, the quiet moments watching a sunset before anyone checks their phone — all of it is intentional.
What To Expect
Before You Arrive
A personal call with Jess: Every guest gets a real conversation to get to know each other, talk about what you're hoping for, and make sure this is the right trip for you. This isn't a sales call. It's a beginning.
A chance to meet your fellow adventurers: We have a group Zoom before the trip. (Our conversation helps you to arrive on the adventure knowing names and faces. Strangers become pre-trip friends. It changes the first day entirely.)
On The Trip
Adventure. Connection. Just enough stillness.
Morning surf or yoga, shared meals, sunset rituals, and conversations that go further than you expected. Standard. (Not left to serendipity.)
After You're Home
The experience doesn't end at teh airport.
You'll have a personal reflection call with Jess. We have a reunion Zoom three months later. And you become part of a community of people who get it, because they were there with you.
Who Is The Founder
~60 Countries | 20+ years of adventure travel | Leadership coach and educator
Jess grew up in western Washington State, dreaming of the places he saw on his grandmother's TV screen. That curiosity took him to Beijing in college, to Europe in 2008, and to nearly 60 countries since. He's led scuba expeditions in the Bahamas, surfed the breaks of Puerto Rico, climbed Mt. Kilimanjaro in Tanzania, and spent more evenings than he can count around tables with people who became lifelong friends.
He's not a tour guide. He doesn't narrate history or hand out itineraries. He asks questions, listens, and creates the conditions for something harder to manufacture: real connection. His gift is helping others feel seen. And he's never led an adventure that didn't give him as much as it gave the group.
What's The Investment
$3,000 per person
Includes accommodation, all meals from a private chef, activity instruction, ground transport, pre-trip calls with Jess, and his personal hosting throughout.
Flights not included.
Think about what it would cost (in hours of research alone) to find the venue, hire the instructors, source the chef, plan the meals, and somehow assemble eight people worth traveling with. That's what we do. So that when you arrive, the only thing left on your list is to experience the adventure.
Ready when you are.
Groups are small by design. When a spot opens, it goes quickly. If this sounds like your kind of adventure — reach out, and let's talk.
What Are Upcoming Experiences
SURF
SURF
SNOW
SNOW
MOTO
MOTO
TREK
TREK
WINE
WINE