How I Ruined My Family Vacation (And How I Did it Better)

Making a Family Vacation Meaningful

I approached our first vacation as a new family the same way that I would vacation as a single adult. The results were somewhat dismal. Before I had a family, I would escape to some exotic surf spot around the world, and spend all day out in the water, then hang out with friends, eat and do it all over the next day.

So, when I planned that early family vacation, it was to a hot surf spot. Although I was having a great time, I realized that I was leaving my wife to fend for herself each day with our two small children. This was not a family vacation, but my vacation.

Time to adjust course! What transforms a simple getaway into a meaningful experience for the whole family? After a bit of forgiveness, we came up with three goals that must be met for each family excursion.

It’s not just about the destination; it’s about how the trip brings us closer. Here are three key ingredients—inclusion, discovery, and reset—When met, our family vacations became truly fulfilling, leaving everyone renewed and reconnected.

1. Inclusion: Togetherness is the Heart of the Adventure

A meaningful vacation starts with everyone feeling like they’re part of the journey. Whether there are toddlers, teens, or grandparents in tow, the best trips are ones where no one’s left on the sidelines. Inclusion means picking activities that everyone can enjoy together.

Days of just me surfing or playing golf were out, days of hiking, fishing, boating, etc. were in.

When everyone’s included, the vacation becomes a shared story, not just a collection of individual highlights. It’s the difference between “I had fun” and “We had fun”—and that “we” is what makes it unforgettable.

2. Discovery: Learning and Growing as a Team

There’s something magical about facing a challenge or learning something new together—it sparks camaraderie and gives my family a shared sense of triumph. Discovery doesn’t have to mean scaling a mountain (though it could!). It’s about stepping out of our comfort zone as a unit, whether that’s mastering a new skill, navigating an unfamiliar place, or overcoming a small obstacle.

For example, we learned to sail as a family. There are so many tasks aboard a boat such as navigating, sail trim, steering and tending the rig, everyone could have a job and each person was needed. We had the task of reaching a new destination and then celebrated each person’s part in accomplishing this task.

These experiences didn’t just teach us something new; they taught us about each other.

Who’s the encourager? Who’s the problem-solver? Who can read the wind the best?

Discovery fuels bonding through shared effort and growth. It’s a reminder that our family is a team, capable of tackling anything—on vacation and back home.

3. Reset: Recharging and Realigning as a Family

A meaningful vacation isn’t all go-go-go—it needs space for a reset. This is the time to unwind, recharge, and reflect on what matters most as a family. After all, the goal isn’t just to escape normal life but to return to it stronger, with a renewed sense of purpose and connection.

Downtime in the evenings in the cockpit of a boat, or the porch of a cabin, or around a campfire, where we would discuss our favorite parts of the day.

The key is balance: pair the excitement of discovery with the calm of reflection, so we would head home not just rested, but reconnected.

What Helped Us Meet Our Goals

We found that cruising on a sailboat helped us to accomplish these three goals the best. Everyone is part of the crew, we discover new places together and have fun relaxing after we drop the anchor each evening. We still do things like winter ski trips and beach camping, but we always come back to sailing.

That is the reason we have developed Family Sailing Vacations at The Sailing Academy. We enjoy taking care of all the details and helping families learn to sail a yacht together with the guidance of an instructor. If you think this might be a good option for your family, look for more information on the website or give The Sailing Academy a call at 410 867-7177.

If you have found a special activity that works well for a family vacation, drop me a note. I am always looking for new opportunities to bring my family together, by learning something new in which we all can participate.