I’m Retired and Regret Waiting Too Long To Take These 5 Trips
Written by
G. Brian Davis
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Amen Oyiboke
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There’s always a reason to push trips to “next year.” Busy jobs, demanding kids, pinched budgets — there’s never a convenient time to take dream vacations.
The window of opportunity often closes before you realize it, however. Take it from these retirees, who regret missing out on their dream trips when they were younger.
1. Climbing Mount Kilimanjaro
Philip Mire spent 30 years as a cybersecurity and global operations executive. Today, he spends six months a year traveling, teaching scuba diving and writing about his adventures on his blog Spend It Traveling.
“Before my diagnosis of Primary Lateral Sclerosis (PLS), I loved long-distance hiking and the kind of outdoor travel that leaves you sore in a good way. One dream I kept putting off was climbing Mount Kilimanjaro,” he said.
“I always had a reason: one more work goal, one more promotion, one more year. Now, it would take a lot of planning, help and frankly, some luck. It’s hard to look at that and not think ‘Why did I wait?'”
2. Camino de Santiago Trail
Among the most famous hikes in the world, the Camino de Santiago isn’t actually a single trail, but a network of routes that converge on Santiago de Compostela in Spain. They stretch across France, Spain and Portugal, and each “way” spans hundreds of miles.
“I walked a 69-mile section of the Camino de Santiago in 2025,” said Mire. “I finished it, but it wasn’t the version I’d pictured years ago. I was slow and I fell several times on the trail. I had to swallow my pride and adjust everything: shorter days, more breaks, more help.
“I also learned that ‘success’ didn’t look like crushing miles. It looked like getting up, brushing off the dirt, and moving forward again.”
3. Everest Base Camp
Colleen Sims had a similar experience, toughing her way through the Camino after a devastating cancer diagnosis. She ultimately succeeded and shared her story on her blog Then We Walked, but she acknowledges other trips that she’ll probably never take now.
“I wanted to make the trek to Everest Base Camp for a few decades, and almost booked it in my 30s, but like many other travel destinations, I put it off,” said Sims. “I then decided to hike it for my 60th, but pre-existing health conditions meant I struggled getting insurance. And now that my husband Gerry is over 65, it’s difficult to find a company to take us. I have thought of going alone, but I know that time is fast running out for me and I feel it’s just too late.”
4. European Camping Road Trip
Sims also envisioned a road trip across Europe, but worries the window has closed on that trip as well.
“We dreamed of taking a campervan around Europe, but these days, Gerry no longer enjoys driving larger vehicles and age-related vision loss rules this out for me. And equally, we once had a plan to walk around the entire border of France with a tent, but that is now off the agenda,” she said.
5. Family RV Trip Across the U.S.
After decades as an HR executive, Anthony Damaschino now writes books. He points out that unexpected health problems aren’t the only challenge that can prevent your dream vacation.
“Looking back, there are a couple of ‘right age, right era’ vacations I wish I’d done when my kids were still young. I always pictured us piling into an RV and doing a long cross-country loop one summer,” said Damaschino. “My wife is an elementary school teacher, so the timing would have been ideal. But swim team, camps, and summer commitments always took over, and by the time the kids were in their late teens, we’d basically aged out of the version of that trip I imagined.
“I tell younger parents to be intentional about the family trips they want while the window is open.”
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