Gentry Jackson exists to inspire passion and purpose through adventure and travel. We offer indelible experiences filled with amazement and achievement. Our multi- environment programs, often involving months of planning and preparation and tailored exclusively to every client, will challenge your perceptions of the natural world and your place within it. Discover your dreams. Discover yourself.


Gentry Jackson Revolutionizes Travel and Redefines Adventure.

Are you a tourist, a traveler...or an adventurer?

Tourists watch through windows, travelers engage firsthand, but adventurers dream of what could be achieved-what might be seen-and make it a reality. A Gentry Jackson itinerary will transform your definition of travel. More than just an escape, our unique experiences are an aspirational bridge to an extraordinary way of living.


Travel, fitness, adventure and luxury are seamlessly blended.

Adventure travel has traditionally been defined by risk and adversity. But Gentry Jackson incorporates luxurious amenities and a private concierge to enhance your experience and achievement.


And the best part?

Gentry Jackson adventures are accessible to everyone. We are flexible and inclusive enough to accommodate all ages and fitness levels.


Curators of Personal Experience

Gentry Jackson is a wildly different brand—an elite event producer for one-of-a-kind journeys. Gentry Jackson will design, produce and manage your adventure on the most personal level, working with you from inception to conclusion. We empower our clients, taking them to places in the world—and within themselves—they never thought possible. All skill levels are welcome in the Gentry Jackson family; it's the desire to seek and achieve that matters.

Luxury is a necessity

There is no longer a need to equate adventure with hardship. Luxury is a part of every Gentry Jackson experience. Each adventure is crafted with first-rate service and detail, and our singular "GJ Moments" involve the truly rare. Such moments invoke unforgettable elements of the following:
  • Natural Beauty

  • Culinary Sophistication
  • Historical Authenticity
  • Legends & Lore
  • Music & Culture
  • Spa & Wellness
  • Trademark Surprises

Your Dream. Your Story. Your Adventure.

GJ Signature Adventures

GJ Signature Adventures can be personalized for the young and old, families and friends, and corporate teams. With individualized training plans, varying levels of experience and fitness are not a problem. The degree of intensity will be dialed up or down as needed, allowing you to go as far as your imagination takes you. Our Signature Adventures will challenge and invigorate your mind, body and spirit; it's a seamless blend of adventure, fitness and luxury you will come to know as the "GJ Way."
  • Gateway Adventures are quests for those with big dreams but little time. These brief getaways are a perfect introduction to the "GJ Way" of adventuring and are also ideal training exercises for full-day journeys.
  • Full-Day Adventures weave together multiple adventure disciplines, terrains and, of course, our unique GJ Moments.  Incorporating activities like rock climbing, cycling and paddle boarding with premium cultural and culinary elements, a full day with Gentry Jackson will leave you exhilarated and eager for what's yet to come. These expeditions are also the perfect training ground for our exclusive multi-day adventures.
  • Multi-Day Adventures are the ultimate expeditions, allowing the widest array of experiences and the greatest rewards. Whether you dream of the crystal clear waters of the Caribbean or the sculpted dunes and majestic mountains of Morocco, Gentry Jackson will craft an unforgettable journey to surpass your utmost travel fantasies.
Gentry Jackson's Full-Day Adventures are highly personalized itineraries that should be booked approximately two months in advance; our Multi-Day Adventures may require four to six months of preparation.

GJ Special Event Adventures at Fairmont Miramar

For those with limited schedules for both planning and playing, Gentry Jackson has partnered with the spectacular Fairmont Miramar Hotel & Bungalows in Santa Monica to offer a few of our favorite local, single-day adventures.
  • The Malibu Trifecta: Malibu, the iconic California setting, is our fitness and adventure playground. This adventure includes rock climbing, hiking, cycling, and ocean activities.
  • So Cal Trifecta: Dare to conquer all Southern California terrains in one day? Your private aircraft will transport you from Santa Monica to Joshua Tree National Park for rock climbing, to Big Bear for mountain biking or snowboarding and skiing, and to Catalina for ocean activities based off a private catamaran. This event is quintessential Gentry Jackson and the epitome of adventure in Southern California!
  • Adventures Under the Stars: Traveling the mountains by night is an experience filled with mystery and wonder. The darkness provides for introspection and privacy while transporting adventurers into an almost otherworldly realm. We will trek, rock climb, paddle, and mountain bike under a canopy of stars that urban dwellers never see. These moonlight treks are coordinated with celestial events like meteor showers and are filled with classic GJ Moments.
  • Dawn Patrol: Prefer dawn to dusk? Our Adventures Under the Stars can be flipped to begin in the youngest hours of the day. You will enjoy the same remarkable range of activities as moonlight slowly gives way to the splendors of sunrise.
Certain activities in Gentry Jackson's Special Event Adventures are based on seasonal availability. Specific dates and start times may vary depending on the phase of the moon, celestial events, weather and seasons.

Your Guides

As your advisors, allies and guides, the Gentry Jackson team sets the highest standards for the industry. From start to finish, we patiently and expertly conduct clients through their adventures, with premium resources and personalized service; our clients always know we are there for them at every step. We invite you to join us in our passion for luxury and adventure. Gentry Jackson will help you discover your finest self as you enjoy the natural world at its most glorious.

  • Ryan Gentry

    For two decades, Ryan has traveled from the pyramids in Giza to the ruins of Machu Picchu, most often to prepare individuals for expeditions, races, and endurance events. He is a certified Single Pitch Instructor with the American Mountain Guides Association, Wilderness First Responder, Personal Trainer and World Paddle Association Stand Up Paddleboard Instructor. Ryan's experience includes multiple summits of Mount Rainier, several winter traverses of Yosemite National Park, countless excursions into the Sierra Nevada range, ice climbing on New Zealand's Franz Josef Glacier, and rock climbing in Patagonia, Wyoming and California. He has paddle boarded up and down the coast of California, along the Baja Peninsula, and throughout the Caribbean and Hawaiian islands. His adventure education includes coursework with Wilderness Leadership Institute in San Diego, Rainier Mountain Guides in Seattle, Ice Axe Expeditions in Truckee, and advanced training in snowboarding.

    At the same time, Ryan has become highly sought after for his expertise in injury prevention, post-surgical rehab, and functional training. In his pre-peripatetic days, he worked for Harvard Business School and S&P Micropal after receiving a degree in business management from Bentley University.

  • Josh Jackson

    Josh has fervor for both outdoor recreation and teaching, and he has spent almost two decades dedicated to his passions. Josh has worked as a climbing, river and mountain guide throughout the West and Alaska. He has his Bachelor's degree in Adventure Education and Wilderness Leadership from Prescott College and a Master's degree in Outdoor Experiential Higher Education from the University of Alaska Fairbanks. Josh is a certified Wilderness EMT, Whitewater Rescue Technician and AMGA Rock instructor. In addition to working as an Outward Bound instructor, climbing gym manager, wilderness therapy facilitator, field program manager and the Outing Director for The University of California San Diego, he has served as adjunct faculty at colleges and universities, teaching such courses as expeditionary sea kayaking, white water rafting, rock climbing, backcountry skiing, ice climbing, surfing, winter camping, map & compass, adventure education and wilderness leadership.
    Josh is the Executive Director of Wilderness Leadership Institute, teaching courses in all program areas, as well as being a lead instructor for Wilderness Medical Associates and an SPI Provider for the American Mountain Guides Association.

  • Allen Giernet

    Allen is an extreme outdoor enthusiast with an undying passion for anything and everything outdoors. With over three decades of outdoor adventure experience, he has logged hundreds of thousands of vertical feet split board mountaineering in the Eastern Sierra Nevada, Washington Cascades and Montana. Adding innumerable miles of backcountry travel, rock climbing and camping throughout the West, ocean kayaking in the Sea of Cortez and along the California coast, he is well equipped for any adventure.

    He is a certified Single Pitch Instructor with the American Mountain Guides Association, a Wilderness First Responder, Avalanche level II trained, a member of the American Avalanche Association, a World Paddle Association Stand Up Paddleboard Instructor, and was the vice president of Team Mountain High's youth training and competition snowboard team for seven years He also holds 3rd place overall for two consecutive years in the USASA snowboard competition circuit. In 2014, Allen received the National Ski Patrol John Hanson Memorial Award for outstanding avalanche instructor.

    Allen is the founder and director of SoCal Snow Avalanche Center, a non-profit promoting safety and education in the local mountains. He has partnered with the National Ski Patrol to help instruct avalanche-training programs in the Southwest. 


Our Logo

The Dwennimmen is a symbol, or "adinkra," used by the Akan people in Ghana. Derived from the curve of ram's horns, the Dwennimmen represents strength, grace, integrity, and the search for wisdom. As W. Bruce Willis notes in his Adinkra Dictionary, "A person may be talented and gifted and may have skills and knowledge, but it is not these virtues alone that enables one to excel. It is the creative use of these skills; the strength in mind, body, and soul; and the humility that comes from understanding one's place in the universe."