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Travel with Teens

As our children grow and move into the teenage years, they increasingly are thinking more about trying on different looks and identities in light of how they see and mix with their peers. During these challenging years, adolescents face a number of social and academic challenges, especially at the age of moving from middle school to high school. As parents, we face our own challenges in figuring out how to provide love, structure, support, and get some time with them.

Multi-day trips involving the outdoors can still provide us opportunities, although we may have to adjust on exactly what our teenagers want to embrace and share as outdoor adventures. For me, I realized this year that my daughter and I were entering this transitional period.

I could sense her starting to separate from me and become more independent. Her mother was experiencing the same. I noticed how much more important her time with (and attention from) her peers was becoming in relation to making choices.

As I considered two of the week-long trips we would take together, I stepped back to think about how to create multi-day trips that still provided us with outdoor adventure opportunities while securing her support and desire to participate. A five-day rafting trip or hiking trip did not appear to have the same appeal as it did the last two years.

We began the planning six months prior given one trip would likely involve air travel. We came up with some criteria like warm-weather vs. cold-weather destination; road trip vs. air travel; 4 days vs. 7 days and so on. Once we narrowed down these general parameters I came up with four destinations and then let her pick the two we would travel to for the week-long periods we would have together.

The selections ended up being Maui, Hawaii, and Mission Beach, California. With the locations selected, I booked accommodations, travel, and made other general arrangements. We went to a bookstore together one weekend and jointly shopped for a few travel guides, maps, and magazines about the locations and interests. I bought each of us a copy so we could read while apart and spend time over the phone and online to make further plans.

Maui-with-a-teenI came up with a budget for activities for each week, eating out, souvenirs, and how much money I would provide her to spend in addition to what she would bring from savings and work. I then prioritized the activities I wanted to do and asked her to create a list of her priorities. Once we got these down, we then began to discuss and work together to create a final list. Sharing your respective thoughts and priorities, negotiating how to use the time available, and reflecting on your experiences will help you both learn more about the other. (And your kid may notice that you’re an actual person, not just a parent.)


Our first week-long multi-day trip this year was the one to Maui. We researched snorkeling places and selected four around the island to make half-day trips to try out. Some of the places were Black Rock, Slaughterhouse Beach, Honolua Bay, Chang’s Beach, 5 Graves, and Maluaka Beach. Some days we saw an amazing array of fish and sea turtles and on others not so much.

Hikes to Nakalele Blowhole (check tide schedules, as high tide provides the greatest opportunity to see it "erupt"), Olivine Pools, and up the Pipiwai Trail were fun and challenging. Between some hikes and our drives, we saw amazing lava arches.


We took a day and drove the road to Hana, but in reverse. It happened to be the day it poured rain. Driving the route in reverse meant we faced a lot less traffic both on the road and at stops.

Oheo-gulchWe really gained an appreciation for just how much water can fall in a short period of time and raise streamflows. Two of our desired hikes (Alelele Falls and Hahalawe Falls) were wiped out by the fact the water was too high and fast to cross safely to get to key waterfalls. Some we did see were Punalau Falls, Upper Waikani Falls, Wailua Falls and hike, 7 sacred pools at Ohe’o Gulch and above it, the Pipiwai Trail hike (one of the best on the island), and Kukui’ula Falls. This last one sits inside part of Haleakala National Park that extends from the top of the crater down to the ocean.

Kapualua-ZiplineWe also went whale watching and were astounded at just how many whales you can see right from the beach. A big adventure she wanted to try was taking the Kapalua Ziplines tour from high above Kapalua. It included one 2,300-foot line.


The second multi-day trip was a road trip from Portland, Oregon, area to Mission Beach, California. We broke the drive into two days. Our second day included driving and hiking along the Big Sur coastline. We did short hikes around Garrapata State Park, Pfeiffer Beach, Pfeiffer Big Sur State Park, Partington Cove and McWay Falls.


Once we arrived in Mission Beach, we spent a lot of time doing long walks in the morning and short bike rides. My daughter picked paragliding as one of the big adventures to try. We went to the Torrey Pines gliderport, where she and her pilot launched off the cliff for an amazing flight.

I flew my niece (who is my daughter’s same age) out on our fourth day into San Diego to join us for four days. Once she arrived they explored on scooters, walked the beach, and tried out boogie boards and surfboards. We saw a lot of wonderful sunsets. Our KEENs were used to transport us on many of these adventures.

cousins-on-the-beachThe two multi-day trips were fun, rewarding, and presented challenges that arise between parents and teenagers. Still, I treasure (and believe she does, too) the time we spent together. She clearly was engaged in the activities and adventures she had selected we do.


Without exception on all of the trips we have made, laughter has been the rule in each case we accomplished what we set out to do. I have been privileged that my daughter has given me great moments of joy and laughter and also sobering moments of insight and humanity while driving in the car. My takeaways to share are:

Much of the trip is up to them at this age. You will map a route or itinerary for your multi-day trip, but there is no planning for how this multi-day trip will impact your teenager(s), what they will take away from it, and how they will respond to the entire time you are engaged in it. Our teenage children are becoming their own people, so they will shape their own narrative. Ignore at your own risk.

Be ready to make room for a friend. It’s worth considering to allow them to bring a friend for all or some of the trip. It can be rewarding as well as it will create a different dynamic. Expenses can go up but it can also allow for smile-widening experiences when they share an activity they enjoy and have fun.

Sometimes you have to get out of their way. As the parent, we have both physical and mental differences that can stand in the way of how they experience a new place. With structure, communication, and trust, you may want to work with them to figure out how they can do some things without you to create their own memory and story narrative.

Their music isn’t always your music… and that’s OK. I love music. It has helped create triggers for memories of certain events and points in time on a trip. I have always wanted my daughter to feel this is something we can share. On these two trips, I released my grip on my iPhone and the Bluetooth so she could take control and play her favorite music for us to listen to jointly. In doing so I was rewarded with watching her enjoy songs that give meaning to her, share in singing new verses together, and by giving away control, she voluntarily would select a playlist of mine to play.

gliderport-torrey-pinesTalking may not always just spring forth, but you can nurture it to create a bonding experience. Having engaging conversations with our teenagers can be challenging. Driving in a car where you are sitting side-by-side, on a beach or in a similar configuration can provide an easier format than when directly looking at each other. Finding something to use to initiate a conversation can range from a song to a book they have read, to challenges they face to asking them to share great photo posts or making up stories about people you see.

Connect your teenager’s self-worth to their level of effort given. No matter what we encourage our teenagers to participate in outside, we want to focus on their effort all the time and not just the outcome. Reinforcing effort creates more resilient kids when they fail or experience rejection.

Anticipate the social media battle. Social media and their phones are part and parcel of their lives. Knowing they are going to want to be connected, we worked to find common ground around when that takes place when they turn them off, and ways to use it to build shared experiences and fun. I had her use her Snapchat to create photos I could post. We would both take photos and then decide on who would post what. Being willing to have my photo taken with her or separately letting her select filters went a long way.

Be flexible. What you agree to months ahead to do on a trip can change when you get to the location. With new information you gather from local sources, weather changes, interest changes, and remaining resources, activities prioritized prior to leaving can change. Pre-paid commitments we held, but we did hold back on locking into everything, which turned out to be critical as we both found some other adventures and activities we wanted to do and the weather did affect our on-site experience.

And thinking about me and an outdoor brand, KEENs have been a part of my adventures, journeys, outings, and everyday life now for over 20 years. Every day I open my closet and there are three pairs of KEENs alongside the other shoes I use to transport myself. Not every day do I get to put them on or pack them for the adventures and travel I so love, but every day they are there for me to see and think about, “What is the next bridge in my life I will cross with those KEENs on my feet?” I hope over the years, my daughter will also embrace how a favorite piece of outdoor gear like Keens can help bridge the challenges and opportunities she will encounter when we are apart.