How Many Vacations Do You Have Left?
It’s a simple question.
But when was the last time you really stopped to think about it?
Not just this year.
Not next year.
Your lifetime.
How many vacations do you have left?
And maybe that’s exactly why we shouldn’t keep waiting.
We Always Think There Will Be More Time
I’ll take that trip when work slows down.
After the kids graduate.
When I retire.
When airfare comes down.
Next year.
I’ve heard every one of those reasons over the years, and if I’m being honest, I’ve probably said a few of them myself.
Life has a way of filling our calendars before we even realize it. School starts. The holidays arrive. Work gets busy. Family needs us. Before long, another year has come and gone.
Sometimes we get so caught up planning for someday that we forget today is happening right now.
A Conversation That Changed My Perspective
Years ago, when my children were still very young, I met a woman who unknowingly changed the course of my life.
She and her husband had always planned to travel after retirement. They worked hard, saved their money, and looked forward to the day they would finally have the time to see the world together.
But life had other plans.
By the time they retired, her husband was on dialysis, and the adventures they had spent years dreaming about were no longer possible.
She looked at me and said something I’ll never forget.
“Don’t wait.”
Those two simple words stayed with me.
In that moment, I promised myself I wouldn’t wait until retirement to introduce my children to the world. Instead, I started taking them overseas while they were still toddlers.
Were those trips always easy?
Not at all!
Traveling with toddlers meant extra planning, plenty of patience, and occasionally carrying someone who decided they’d had enough walking. But every challenge was worth it.
Today, when I look back, I don’t remember the long flights or the tired moments. I remember watching my children experience the world with wide-eyed wonder. We laughed as we raced down the hills of Austria on a rodelbahn, sang along on the Sound of Music Tour through Salzburg, tried foods we’d never tasted before, and met people whose lives looked very different from our own.
Those experiences helped shape who they became and gave us memories we’ll carry for a lifetime.
If you’ve ever wondered whether young children are “too little” to travel, I encourage you to read my blog, How to Turn Your Toddlers into Travelers, where I share some of the lessons our family learned along the way.
Every Season of Life Brings a New Reason to Wait
Today, all three of my children are grown and building lives of their own.
Getting everyone together isn’t nearly as easy as it used to be. Between careers, relationships, and busy schedules, finding a week when everyone is available can feel like solving a puzzle.
And I know the next chapter is coming.
One day there will be grandchildren. There will be school calendars, sporting events, dance recitals, birthday parties, and all the wonderful chaos that comes with growing families.
Every season of life is something to treasure.
But every season also gives us another reason to say, “Maybe next year.”
I’m so thankful I listened to that woman all those years ago.
Because if I had waited, I wouldn’t have shared those adventures with my children while they were growing up. Those memories belong to all of us now, and I wouldn’t trade them for anything.
Travel Is One of Life’s Greatest Educations
People often ask me why I travel so much.
It isn’t because I enjoy airports.
Or packing.
Or twenty-hour flights to Australia.
I travel because of what travel teaches us.
I’ve always believed that one of the greatest educations we can give ourselves—and our children—is the opportunity to experience another culture firsthand.
You can read about Austria, Australia, or New Zealand in a book.
You can watch a documentary.
But it’s something entirely different to race down an alpine mountain on a rodelbahn, stand beneath Uluru at sunrise, hear a Māori welcome in New Zealand, or sit around a table sharing a meal with locals.
Travel has a way of bringing history, geography, culture, and people to life in ways a classroom never can.
Every trip teaches us something—not just about the destination, but about ourselves.
Travel has given me sunsets over Uluru, waterfalls in Milford Sound, wine with kangaroos just outside my cabin, and countless conversations with people I’ll never forget.
It has also given me something even more valuable—the opportunity to watch my children discover that same sense of wonder.
Those aren’t simply vacations.
They’re pieces of my life story.
So…How Many Vacations Do You Have Left?
I hope the answer is…
More than you can count.
More places to explore.
More cultures to discover.
More meals shared around unfamiliar tables.
More sunsets.
More laughter.
More memories with the people you love.
None of us knows how many vacations we have left.
But we do get to choose how we spend the time we have.
So take the trip.
Take your children while they’re still young enough to see the world through eyes of wonder.
Take your parents while they’re still able to enjoy the journey.
And one day, if you’re lucky enough, take your grandchildren and watch them discover that same magic.
Celebrate that anniversary you’ve been talking about for years.
Reconnect with old friends.
Watch another sunset.
Taste something you’ve never tried before.
Because in the end, the souvenirs fade…
The memories never do.
Originally inspired by my 2019 blog How Many Summers Do You Have Left? Updated and expanded in August 2026.
Lisa Rossmeissl is the owner of Boomerang Escapes, a home-based agency located in Branchburg, New Jersey, and North Myrtle Beach, South Carolina, with agents in TN, MS, ID, and WI.
She has been a professional travel consultant since 2008 and specializes in Australia and the South Pacific. Australia, New Zealand, Tahiti, Fiji, and Cook Islands are among the specialist certificates she holds. Her agency’s focus is on creating custom itineraries with their client’s wants, desires, and budgets in mind. She and her planners believe in getting to know the traveler to ensure they have a vacation to remember. With each planner specializing in a different market area, Boomerang Escapes can offer a wide variety of leisure vacation planning.