Are you planning a baby
boomer trip that includes your parents? Need expert advice? Meet Sherry Ott of Ottsworld, today’s guest writer. She’s sharing her experience of planning a trekking trip to Nepal with her 73-year-old father. Neither Sherry nor her dad are technically baby boomers (born 1946-1964), but you’ll still benefit from the trip planning strategies that Sherry explains.
Does the thought of traveling with your parents bring visions of bus tours with everyone wearing the same t-shirt, while following a person with a loudspeaker through the streets of Florence? That’s enough to make me never want to travel with my parents! Does traveling with aging parents mean that you can’t do what you want to do? Not exactly, sometimes you just have to find compromise.
I may not officially be a Baby Boomer; I’m 40 and have been corralled into the GenX pasture. However I do have “almost” Boomer age parents; they are 73 years old and I am the youngest of their children. When I invited my father to join me on a 21-day hike of the Annapurna Circuit in Nepal, I knew it would be a challenging trip. However, it would be worth it to spend time with my dad doing what I love, as well as providing him a chance to see the magnificent Himalayas.
There were many challenges to overcome, but the first hurdle was how to go about planning a trip with my 73-year-old father. I’m a very active person who has been traveling for the last 3 ½ years. I’m comfortable in developing countries, roughing it, living very cheaply, and lugging backpacks around. I like to show up in a destination with no plans and make my itinerary on-the-fly. I’m cheap. I stay in hostel dorm rooms and take local transportation. However, could I realistically do that with my dad? Probably not. I had to figure out how to organize a trip for him, and for me. I needed an itinerary spanning generations, and activity level.
I started out considering my dad’s travel pluses and minuses around some key areas – activity level, comfort level, safety, and travel experience.
Plus:
- He is active, even though he’s 73, he doesn’t sit still. He walks, lifts weights, mows the yard with a push mower, gardens; and it wasn’t too long ago that I saw him make a diving catch for a softball while playing with grandkids.
- He’s capable of roughing it. He comes from a Nebraska farming background, growing up in the depression; roughing it pretty much describes his childhood.
Minus:
- Has only traveled to one undeveloped country, Ecuador, on a business trip. I wasn’t quite sure how he’d handle the poverty, dirtiness, unstable government and lack of infrastructure of Nepal.
- Even though he was fit, I had to consider what would we do if he got sick due to food, fell and twisted his ankle, got altitude sickness or simply just couldn’t complete the 17 day trekking circuit.

First, I knew we had to go it alone because we needed flexibility. Sure, it’s fun and economical to trek with groups, but I knew that group itineraries weren’t flexible enough. My dad might need extra rest days or simply want to stop trekking early one day.
Second, I would pay a bit more to have a tour pre-booked before we arrived and completely catered to us. As much fun as it is to plan spontaneously, I knew that I couldn’t do that with my dad. I needed to have some structure for him.
Third, I wanted a guide AND a porter. Most people would say that’s overkill for only two people, however I didn’t want my dad to have to carry anything heavy thereby reducing risk of injury.
Fourth, I knew I had to ease him into the undeveloped world by starting off with more creature comforts and slowly removing them. Thereby trying to control the shock of Nepal.

Giri also helped me arrange a comfortable hotel and car service in the beginning so we could ‘acclimate’ to Nepal. However by the end of the trip, we were taking buses and staying in cheap guesthouses with private rooms. I find that slowly adjusting is the best way to tackle undeveloped countries for people of any age.
I thought planning this trip would be the hardest part, but it wasn’t. The key is to take time to talk to your parents and really think about their personalities, strengths and weaknesses. I had to compromise and be willing to plan ahead, slow down, and spend a bit more. Yet at the same time, I wanted to push my father’s limits a bit. After all, as one ages, our boundaries become more and more enclosed which ages us even faster-mentally and physically.
In fact, the hardest parts of the trip were reall
Sherry Ott is a co-founder of Briefcase to Backpack, a website offering career break travel inspiration and advice. She also runs an around the world travel blog writing about her travel and expat adventures at Ottsworld — Travel and Life Experiences of a Corporate America Runaway.
Baby boomer travelers, have you experienced an adventure with a parent (or parents)? Post a comment to tell us about it. I can’t think of a better way to make a lasting memory than to travel together.


