• Jordan Pond from the North Bubble, Acadia National Park, Maine
  • The view from Prest, Aurlandsfjord, Sogn og Fjordane, Norway

Dear Fellow Travelers,

Over thirty years ago, we met as national park rangers and discovered the energizing and soul-expanding joy of hiking in the mountains. In 1996 we launched Walking Softly Adventures and began to offer mountain hiking tours as a way to share this joy with others. In 2008, we began to offer these tours under a new name Mountain Hiking Holidays.

Mountain Hiking Holidays are hiking tours that immerse you in the world’s mountain landscapes. You can expect to be physically active on each day of our trips so they’re perfect for any physically fit person who delights in the challenge of a mountain trail. After more than two decades of leading trips in the mountains, we know that magic happens on the trail. Together we build splendid memories that last a lifetime, memories that continue to inspire and rejuvenate long after the actual experience of travel is over.

This year, please consider joining us in the mountains. Our trips may not be for everyone, but we hope they’re right for you! Ready to hike? We’d love the pleasure of your company!

Happy hiking and happy travels,

Amy and John Osaki
and the Mountain Hiking Holidays team

Who are we?

Mountain Hiking Holidays, Inc. is a Portland, Oregon-based tour operator specializing in mountain hiking trips for hiking aficionados. We’re partial to scenic, high mountain landscapes, so our hiking trips are best suited to those who have a similar affinity for the mountains. While we offer a range of hiking choices on our trips those hikers seeking moderate to challenging hiking opportunities will, in particular, find plenty of hiking options that meet their desires.

Some History

Our company was established in 1996 as Walking Softly Adventures, Inc. and through 2008 we offered our hiking trips (along with a selection of cultural heritage and archaeology tours) under that name. Beginning in December 2008, we began to offer all our hiking trips under the new “Mountain Hiking Holidays” name because that name more accurately and straightforwardly describes the the nature of our trips. (Our cultural heritage tours are now offered under the name, Art Tours by Amy.)

Ever since the first group of Walking Softly adventurers set forth on an exploratory journey to the Italian Dolomites in 1995, we’ve continued to invest our time and energy in developing and delivering high quality hiking trips that put you in touch with the world’s most striking mountain landscapes.

We’d like to thank you again for the wonderful trip you put together for us. The locations, accommodations, meals, variety and schedule made our week as enjoyable as it could possibly be! You are elite professionals; that combined with your individual skills and charm…make your company a wonderful success!



Amy and John Osaki are the founders and owners of Mountain Hiking Holidays and Walking Softly Adventures.

Amy Boyce Osaki is a former park ranger. She has hiked and climbed on six continents and has led mountain hiking trips to the Dolomites, Pyrenees, Carpathians, Maritime Alps, the Cantabrian mountains, Madeira and the Azores, the Olympic Mountains, fjord Norway and western Ireland. Since 1996 she has led forty-six hiking trips in ten countries for Walking Softly Adventures and Mountain Hiking Holidays. While guiding hiking trips she relishes the opportunity to help trip participants connect with the wildflowers, history, language and culture of each mountain region, and she enjoys providing opportunities for the group to photograph the mountains. Amy is an award-winning museum educator who attended university in France. She holds a masters degree in the decorative arts from the renowned Winterthur Museum and is an adjunct professor at Portland State University. She formerly served as the Curator of Education at the Portland Art Museum for six years. Amy is a Certified Travel Counseler, a level of professional certification that is the travel industry’s highest.

John Osaki has spent much of his working career in the great outdoors. He is a third-generation Japanese-American born and raised in Hawaii where he learned French as a second language. His love for the mountains, nurtured among the crags and cliffs of the Hawaiian Islands, deepened during the years he worked as a backcountry ranger in Washington’s Olympic National Park. John spent two decades administering educational programs in national parks and forests and worked in Africa as a consultant to the World Wildlife Fund in ecotourism development for national parks and protected areas in two Central African nations. He has explored and photographed the mountains on six continents. His passion for mountain exploration remains steadfast; during a recent forty-five day period, he set off on the trails of Europe’s mountains ascending a total of 120,000 feet—the equivalent of climbing Oregon’s Mount Hood twenty-five times from Timberline Lodge. Since founding Mountain Hiking Holidays and Walking Softly Adventures with Amy he has led sixty-six trips to seventeen countries on four continents. An accomplished photographer, his photographs are featured on this website and have been published in the travel press.

Trip Leaders and Guides

We never forget that a Mountain Hiking Holiday is your vacation. We firmly believe that the first job of trip leaders and guides is to facilitate your travel experience. Our job is to set the stage and choreograph the trip so you’re free to explore and enjoy. Relax and let us handle the details! Our trip leaders and guides work in concert to assure that your trip runs smoothly and that your outdoor experiences are safe, memorable and rewarding!

We involve only those rare individuals who can blend personality, knowledge and skill to enhance your hiking experiences. Our guides have the necessary expertise and hold the required certifications needed to insure a trouble-free trip. Through their knowledge of place, they help you uncover the stories behind the people and landscapes you’ll experience on your travels. And they work hard to insure that your journey is not only one that’s full of engagement and discovery, but one that’s fun as well! We hope you’ll allow us the privilege of sharing the glories of the mountains with you. We look forward to the opportunity!

Below are some of our trip leaders and guides. Hold your cursor over each image for more information about them.

The Great Wall of China trip was perhaps the best organized trip I have been on due to the group of people, the trip leader and the guides.


We have never experienced travel with leaders who attended to every detail with such dedication. Your company attracts delightful people for a thoroughly enjoyable adventure.


Mike Heilman is the consummate host. He’s easy to talk to, very flexible about meeting your needs and wishes and has a great sense of humor!


Roman’s calm leadership of our hikes added significantly to our enjoyment of the trip.


Steve and Jo were patient and so thoroughly customer-oriented. They bent over backwards to make sure we had the best adventure. They made the trip wonderful.


Asen and Krasi are terrific guides—always helpful, interesting to talk to, and knowledgeable about the area and culture and more.


Patrick and Suzanne were outstanding: prepared, experienced, flexible and always in good spirits. The were…perhaps the primary reasons for our trip’s success.


You have a true gem in Heather and Craig…[they] were a wealth of information regarding area history, flora and fauna. They were very upbeat and spread their time equally between all members of the tour. They were both extremely top-notch and full of energy.


John’s knowledge of the area along with Matthew’s was so comprehensive it was amazing!


You do a wonderful job of caring for your travelers, and we recommend Walking Softly to others.


The whole trip went so smoothly. All the details were taken care of and everyone had plenty of space to do what they wanted. John and Steve were so nice and very accommodating. Thanks for stressing for us!


What wasn’t wonderful about our leaders? You attended to every detail bringing a freshness and enthusiasm to us first-timers.


The skill, warmth and caring that Amy and John put into the trip gives great pleasure. Their courtesy in introducing the innkeepers attests to their positive relationship with staff as well as guests.


I can’t say enough about our hosts and their flawless arrangements, good humor, and concern for everyone’s comfort.


You do outstanding work to let your clients play!


Over many years experience I have never hiked with anyone who had more knowledge of the trails, history and local color than Steve, Jo and John. Within a day or two I knew I was hiking with good friends who happened to be the most professional guides too!


Another unexpected value was in how relaxed we could be. We didn’t have to worry about how to get anywhere, what the trail might really be like and all the hundreds of things that so often add tension to travel.


Craig, Heather and John were all fabulous—great humor, exceptionally organized, really fun to spend time with! They were all sensitive to the various needs of the group, flexible, and full of advice. I felt very pampered!!


Mountain Hiking Holidays

Trips for the adventurous hiker since 1996

PO Box 86250, Portland, OR 97286-0250, USA

503-715-0844 / Toll-free 1-800-313-0345 or 1-888-743-0723


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