• I didn’t grow up traveling luxuriously but my job has allowed me to take my family on fancy trips.
  • My twins have mostly stayed in high-end accommodations and have been to many luxurious places.
  • I worry they’re in for a rude awakening once they grow up and have less access to luxurious trips.

Advertisement

When I was a kid, family vacations meant road trips to the beach or a national park in our station wagon. I didn’t start stamping up my passport in earnest until I was in my early 30s.

I didn’t know anything about luxury travel until even later when my career started to take the form of freelance travel writing.

That’s when I started to get opportunities to trot the globe, staying in the finest hotels with access to rarefied experiences. This happened to be around the time my twins were born — so, unlike their parents, they’ve known nothing but over-the-top luxury travel their whole lives.

And they have no real context against which to compare their experiences.

Advertisement

We live modestly, but my kids are used to experiencing the finer things in life when we travel

Author Alesandra Dubin and her family at Four Seasons CAb

My family has stayed in some incredible villas and hotels.

Alesandra Dubin



Although we live in a modest two-bedroom home that’s pushing a century old and leaks when it rains, our family’s typical travel accommodations are pretty tricked out.

Most resorts we visit set us up in suites with amenities like private pools, personalized chocolates, and massive soaking tubs in multiple marble bathrooms.

My kids spent the summer they turned 10 between trips to the soaring five-star Shangri-La Tokyo and the sprawling new Four Seasons Cabo del Sol on the Cabo San Lucas coast.

Our suite at the Four Seasons sprawled over more than 2,000 square feet — considerably bigger than our house in Los Angeles — with its own pool and an outdoor shower tucked into a meandering, manicured private yard.

Advertisement

The summer they turned 8, we stayed at a beachfront villa on Canouan, a Caribbean island with a reputation as the place billionaires go to escape millionaires. We got there by private plane.

My kids get this special access not because of their family’s tax bracket — like many of the other guests on properties we visit — but because their mom is a luxury travel writer whose work affords unique opportunities.

But they’ve never really traveled any other way, and they’re surely in for a rude awakening when they grow up and hit the road for themselves, using their own age- and income-appropriate resources.

I imagine a future in which their college friends arrange a low-budget spring-break trip, and they’re utterly dumbfounded by the real-world conditions.

Advertisement

I know those types of carefree trips are sometimes the most fun — I was a frequent camper and serious destination hiker before I had kids. But luxury travel is all my kids have ever known.

I hope I’m setting a positive example for my kids, but only time will tell

Author's kids at private pastry chef class for kids at Mitsui Kyoto

My kids have gotten used to experiencing perks when we travel.

Alesandra Dubin



Traveling luxuriously is addictive and my family has been spoiled by the comforts my job affords us.

Although I still have my camping gear, we tend to embrace the finer side of travel during my kids’ limited and circumscribed time off from school.

I like to think I’m setting a positive example for my kids: I work hard at my own business, one I hustled to build up after a layoff from a corporate job. I hope they’ve learned from me that work can be fun, rewarding — and yes, glamorous — when you lean into when you love.

Advertisement

But has their access to luxury travel from a young age skewed their expectations forever? Only time will tell.