Can you Really Do This Full-Time? (Let’s Talk Destination Weddings + Travel Biz)

by Debbie Quain • Updated on April 6, 2026  

So… can you actually make a living planning destination weddings and booking dreamy Caribbean trips?

Short answer: Yep.
Slightly longer anwer: It's a little more spreadsheets and a lot less sipping mojitos by the beach than you might think.

In this laidback Ask Me Anything session, I shared a bit of my own journey—including the doubters, the Yellow Pages ad (yes, really), and how one Jewish wedding opened the door to what I do now. I also talked about:

💍 Why destination wedding are more than just “beach ceremonies”

🌴 What role travel advisors play (and why Google along won't cut it)

📦 Why systems, structure, and logistics matter way more than people realize

👀 And how a curious peacock and an overwater bungalow tour reminded me to actually share what I do

Spoiler: This career path isn't all romance and room upgrades, but if you love organization and oceanside ceremonies, there's nothing quite like it.

If you're a couple considering a Caribbean wedding, someone dreaming about a job in this space, or just a fellow curious human—this one's for you.

P.S. I also talk about how travel advisors get paid (because yes, you deserve to know how this all works; transparency matters around here).

P.P.S. Want to join the next live session of get destination tips straight to your inbox? Hop on the list here

Meet the host

Debbie Quain

Debbie is the host of HitchedAway, an audio guide helping couples navigate Caribbean destination weddings.