Need help planning a skip-gen trip? Here are pro tips from a grandmother who regularly travels with her grandkids. She recommends tuning into their wishes when choosing a destination and plotting out your itinerary. Here’s what you need to know to plan a trip you’ll all remember for years to come.
Nothing makes me happier than traveling with the grandkids. Over the years I’ve planned trips with all three of them or sometimes just the brother and sister team. But now that they’re older, their interests vary. To be certain each of my three grandkids had a special trip to remember this year, I chose to do individual trips tailored to their style of travel. Was it challenging? Absolutely. Was it worth it? Definitely. Consider these tips for planning skip-gen trips with your grandkids.
Things seem simple with younger grandkids. Mine delighted in a trip to the beach, Disney or day trips from home when I visited. But now with grandkids ages 14, 12 and 11, things aren’t so simple. My granddaughter, Katherine (14) wants time to chill out. When I asked her where she wanted to go this year she replied, “I want to stay at a resort at the beach and I want to go shopping.” Her brother, Marshall (12) called me in advance of making summer plans with his request. “TerBear, I need nature and wildlife.” As for my youngest Benjamin (11), “I want to go somewhere that has a lot of seafood.” With all the requests on the table, I began planning.
Choose the Right Designations
With all the kids living in the Orlando area, satisfying Katherine’s request for a beach resort was easy. But, I didn’t want to go somewhere she goes often. The Florida Keys became the clear winner. With all the hassles of flying that plagued the summer months this year, we decided to road trip from Orlando to Key West. Although the initial Florida Turnpike portion to Miami tends to be a bit boring, everything changes once you enter the Florida Keys. Navigating the narrow stretch of land through Florida’s coastal treasure was fun for both of us.
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Meeting Marshall’s request for nature and wildlife, we began our adventure by flying into Denver. His one goal was to step onto the Rocky Mountains and I had the privilege of taking him to the Rocky Mountain National Park. From the moment he spotted the Rockies from the plane window to our explorations within the park, he remained spellbound. From there, we ventured through Wyoming into Nebraska and ultimately South Dakota.
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Benjamin’s hunt for seafood led us to Florida’s oldest town, St. Augustine. With an extensive culture of shrimping, there was plenty to satisfy his appetite. He also expressed interest in historic sites and St. Augustine offers those in abundance.
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Look for Unique Experiences
It turns out Katherine’s interested in much more than shopping. I learned that she’s considering studying horticulture. As a result, I scheduled a visit to the Key West Tropical Forest and Botanical Garden that sits on Stock Island in the heart of Key West. Executive Director Misha McRae shared the story of this curated collection of tropical plants and native species for the Florida Keys and the Caribbean. We strolled through the garden via a network of boardwalks and bridges. We especially enjoyed seeing a collection of Cuban Chugs used by very determined immigrants to cross the Florida Straits to freedom.
The environment matters to Katherine too, so I set up an appointment to tour the Mote Marine Laboratory & Aquarium in Summerland Key. There we met with scientists working to save Florida’s endangered coral reef. We even had the opportunity to participate in coral fragging. Utilizing a specially designed cutting machine, we each cut a small piece of coral that will be attached to the reef to support growth over time. Katherine also loves sea turtles, so a visit to the Turtle Hospital in Marathon provided insights into the rescue and care given to these amazing sea creatures.
Involve Your Grandkids in the Itinerary Planning
Beyond the original requests for specific types of trips, I let the grandkids take control of our schedule when possible. The opposite of his sister, Marshall needs no downtime.
With his insatiable need to find wildlife, Custer State Park outside Rapid City quickly became one of his new favorite places. My initial plans included exploring several areas of the park, but Marshall became fixated on Wildlife Loop Drive on his determined hunt for bison. As a result, I dropped my initial game plan and let him direct me to whatever he wanted to see. We ended up sitting in an hour-long “bison jam” surrounded by hundreds of those majestic beasts and it was an absolute highlight of the trip.
On another day, we managed to hit five of the top attractions around Rapid City: Mount Rushmore, Crazy Horse Memorial, Custer State Park (again) and Bear Country USA. He also tried to convince me we could work the Badlands National Park into the mix. I nixed that one due to lack of time and he’s already saying we have to go back.
Pay Attention to Their Feelings
The old adage “children should be seen and not heard” does not apply to grandkids! When we travel with our grandkids, the point is to enjoy our time together. If something makes them uncomfortable, listen to how they feel and adjust your plans accordingly. For Benjamin’s trip, we had the option to participate in a ghost tour. Before adding that to our plans, I checked with him to see if he was interested. He said yes, but when it came to the tour, we only made it about halfway through. Standing with our group in the Old Jail in the dark freaked him out so we politely left the group early. He also requested sleeping with the lights on that night, so I left everything on until he was sound asleep.
Throw in a Surprise or Two
Although I consult with the grandkids before their trips, I’m always open to adding in a surprise if possible. In Benjamin’s case, that surprise was swimming with dolphins at Marineland Oceanarium, one of the top things to do in St. Augustine. We shared this experience together and it is one neither of us will ever forget. There was pure joy on that child’s face…mine too!
In Key West, Katherine and I made a last-minute decision to embark on a sunset sailing trip which gave us a new vantage point for experiencing the beauty of Key West.
And in Rapid City, Marshall spotted a billboard advertising Bear Country USA and immediately wanted to add that to our adventures. This 200-acre park just south of Rapid City houses black bears, elk, reindeer, cougars, bobcats, bighorn sheep and more. This little detour helped him tick animals off his wildlife checklist!
Don’t Discount the Value of Road Trip Conversations
Having a grandkid that enjoys long road trips means plenty of time for conversations. Eager to see as much as possible on every trip, Marshall has no problem with long road trips and delights at every new discovery. It’s in those moments that you really get to know your grandchild’s personality. Marshall’s a prankster and loves to share stories of being the class clown. He also shares his thoughts about the future which he’s convinced will include some time living in Colorado. He talks as much as I do, so we covered plenty of topics as we checked out new landscapes.
Although Benjamin’s road trip tolerance is limited, on our two-hour drive from Orlando to St. Augustine, we worked in plenty of conversations. On the way to our destination, he asked endless questions about the things we planned to do. On the ride back home, the topics switched to all the fun we’d had and the things he liked most about our time away.
Quieter than the boys, conversations on a road trip with Katherine are interspersed with miles of silence as she listens to her music or catches up on everything that’s happening on TikTok. But when the conversation flows, we learn new things about each other. For example, I had no idea how passionate she was about politics, climate change and the world we live in.
These conversations strengthen our relationships. They provide opportunities to truly get to know your grandchild at whatever stage of life they’re currently navigating. If you have one that’s willing to road trip, don’t miss out on that opportunity.
Honor Their Wishes
Kids often conform to the wishes of adults. They obey their parents. School teachers hand out assignments. And coaches train them to be the best at their chosen sports. But grandparents don’t have to enforce those things. That’s why being a grandparent is so much fun, right?
When I travel with my grandkids, I do my best to honor their wishes. Katherine requested beach time, yet she was more than willing to check out attractions with me too. On our final day, we arrived at Lime Tree Bay Resort on Long Key in the late afternoon. An incredibly family-friendly resort, there were free kayaks, paddleboards, bikes and more available for our use. But Katherine chose to put on her swimsuit, grab her iPhone and spend the afternoon in a hammock on the white sand beach. She wanted downtime; I made sure she got it!
Based in New York City, Terri Marshall is an award-winning writer covering cultural travel, multi-generational travel, road trips, soft-adventure, camping, cars and characters. From hanging out with penguins in Antarctica to fishing for piranhas in Peru to road-tripping through the jungles of Belize, Terri’s always up for an adventure. Drop her into a landscape filled with mountains, towering evergreens, waterfalls and a glacier or two and she’ll be in heaven. But what thrills her most of all is traveling with her teenage grandkids.
Terri serves on the Diversity, Equity, Inclusion and Accessibility Committee for the North American Travel Journalist Association (NATJA). She also serves as the First Vice-Chair of the Eastern Chapter for the Society of American Travel Writers (SATW). In addition to writing for SheBuysTravel, Terri’s publication credits include AARP, Island Soul, Girl Camper Magazine, A Girls Guide to Cars, CHILLED, World Footprints, North Hills Monthly, Alaska Business Monthly, Alaska Contractor and more. Follow her on Instagram at TrippingWithTerri.
