When the Travel Advisor is Also the Daughter and the Mom
What planning Hawaii with my parents and my son is reminding me about family travel.
Next spring, I’m heading to Hawaii with my parents and my youngest son. Three generations, two islands, and plenty of decisions to make before we ever get on a plane.
You might think planning my own vacation would be easy because I do this for a living. My professional experience certainly helps. But when it’s your own family, you’re thinking about much more than hotels and transportation.
I’m the travel advisor making sure the pieces fit together. I’m also the daughter thinking about my parents’ comfort and the mom wanting her teenage son to have a wonderful time.
And somewhere in all of that, I’d like to enjoy a vacation, too.
One destination, different wish lists
Choosing Hawaii gave us a destination. It didn’t automatically give us a plan that works for everyone.
I’m considering experiences like Pearl Harbor, time on the water, exploring Maui, and a stay at Disney's Aulani.
But each possibility brings another question: How will this actually feel for the four of us?
An excursion might sound incredible, but how long is the day? How much walking does it involve? Is there somewhere to sit comfortably? Will we have energy left for dinner afterward?
With a teenager along, I also want room for something active and fun. I’m looking at possibilities like a surf lesson or snorkeling, while thinking through how my parents could enjoy that time comfortably, too.
This is where the planning becomes personal. I’m looking beyond whether an activity is popular and considering whether it belongs in our trip.
I’m paying attention to the ordinary moments
The big experiences are exciting. But I find myself spending just as much time thinking about what happens between them.
How far will we need to walk to get a meal? What does getting from our lodging to an activity involve? Are we making an already full day harder by adding another stop?
My parents are comfortable with shorter walks, so distances matter. A place can look close on a map and still be inconvenient for the people staying there.
These details may never appear in a vacation photo, but they affect how everyone feels throughout the day. When I plan for clients, I want to understand those same things about their families. The more I know, the better I can help them choose.
Together doesn’t have to mean every minute
One thing I’m keeping in mind is that we don’t all have to do everything.
If Tennyson and I want to try something more active, I want my parents to have an appealing option of their own. And if they’d enjoy a slower morning, that doesn’t have to hold up the whole group.
I don’t want anyone to feel they need to keep up, or that they’re missing the vacation because they skipped an activity.
We can share a meal afterward and hear about each other’s day. That counts as time together, too.
My advisor brain wants to fit it in. My mom brain knows better.
There is so much I’d love for us to experience in Hawaii. It’s tempting to keep adding one more thing.
But I’m reminding myself that moving between islands takes time, an early start affects the rest of the day, and everyone needs a chance to settle in.
I want to leave space for a longer breakfast, another hour by the water, or an evening when we decide an easy dinner sounds perfect.
A well-planned trip should give us choices once we’re there. It shouldn’t leave us feeling obligated to follow a schedule when we’d rather slow down.
This is why I care about the details
Planning this trip is reminding me how much trust is involved in handing your family’s vacation to someone else.
You’re hoping they understand the people you love. That they’ll notice the details you might not know to ask about. That the trip will work for your family as it is today.
For me, this is the heart of Awe Luxury Travel. Luxury can be the relief of having someone think ahead, help you prepare, and look out for you along the way.
Our Hawaii trip is still taking shape. I don’t have a story yet about our favorite day or the moment we’ll all remember. Right now, I’m doing what so many of you do: imagining the possibilities and hoping to make something special for my family.
I just happen to be wearing three hats while I do it.
Thinking about a trip with your children, parents, or extended family? Tell me who’s coming and what matters to them. That’s where we’ll begin.
