Behind the Scenes at Island Travel Group
What's Really Happening Behind the Scenes at Island Travel Group
By Jennifer Wayland | Island Travel Group
People often ask me what my day looks like. And honestly? It's never the same twice. That's one of the things I love most about this work — and one of the things I think most of our clients never get to see.
So today, I'm pulling back the curtain. Here's a real, honest look at what's happening behind the scenes at Island Travel Group right now — the team, the trips, the hustle, and the heart that goes into every vacation we plan.
The Team That Makes It All Happen
Island Travel Group is not just me. I want to make sure you know that.
Behind every booking, every payment reminder, every "your cruise documents are ready" email, there is a team of talented, travel-passionate advisors who show up every single day with dedication I am genuinely proud of.
Our Travel Manager. She is the one on hold with Princess Cruises advocating for our clients, carefully reviewing booking confirmations line by line, and making sure every detail is exactly right before it reaches your inbox. When I send her something in the morning, she's already three steps ahead of me by afternoon. I don't know what I'd do without her.
She manages so much of our behind-the-scenes client communication workflow — the automated reminder emails, the pre-departure checklists, the systems that make sure you hear from us at exactly the right moments before your trip. She's thoughtful, meticulous, and genuinely cares about the client experience.
Our team of travel advisors is spread across the region, each with their own areas of expertise and their own loyal clients. They book Sandals honeymoons, family cruises, European adventures, VRBO beach rentals, and everything in between. They're the ones texting me on a Friday afternoon with a great find for a client, and I love them for it.
This is a real agency, with real people, doing real work for real travelers. And that matters.
What a Typical Day Actually Looks Like
Let me give you a peek at a real day at Island Travel Group.
By mid-morning, my Travel Manager and I are already back-and-forth on a client booking — working through three different flight options due to a schedule change - out of O'Hare, Indianapolis, and Peoria, comparing schedules and prices, and then drafting a clear email so the clients can review everything together when they get home. It's the kind of detail work that takes time to do right, but it's exactly the kind of thing that separates a great travel advisor from just clicking "book" on a website.
Simultaneously, I'm responding to a travel insurance representative about a rescheduled team training, forwarding a VRBO confirmation to add to a client's file, and sending a note about a change of address due to a check that got returned in the mail.
By afternoon, I'm reviewing reminder group templates to make sure the automated client communication we send before every trip is personalized, relevant, and perfectly timed. Not just "your trip is coming up!" — but the right message, at the right time, for the right trip. That's a system we've been building and refining for years.
And somewhere in between all of that, I'm meeting with new supplier partners, researching new destinations, and thinking about what's next for you — our clients.
The Trips We're Working On Right Now
At any given moment, we have trips in every stage of the planning process. Here's a glimpse of what's on our desks right now:
A Greece sailing — Guests are joining us on an Aegean cruise this fall, and we've been managing their payments, optional tours, and pre-cruise hotel in careful stages. When you travel with Island Travel Group, we don't just hand you a confirmation number. We walk with you through every step, every payment, every question.
A Princess cruise — This booking has been a lesson in persistence. Between booking transfer paperwork, airline options, and working directly with Princess partner support to resolve a billing situation, we've spent weeks making sure this trip comes together exactly right. That's what advocacy looks like in this business. We don't give up on your trip.
An Alaska group — We're building out pre-departure excitement for our upcoming Agent-Hosted Celebrity cruise and Alaskan rail adventure, complete with "Your Adventure Awaits" postcards, a ship-specific fact sheet, and a full suite of automated emails to make sure every guest feels prepared, excited, and taken care of.
A VRBO beach rental — One of our advisors is handling a condo rental at Turtle Bay, Hawaii. (And yes, I may have mentioned in an email that I wish I had a condo there myself. 😄)
The Part Nobody Sees
Here's what I want you to understand: when something goes wrong on a trip — a flight gets changed, a resort has an issue, a payment gets miscoded — you are not alone.
You are calling people who know your name, know your booking, and will fight for you.
We spend hours on hold with cruise lines advocating for clients. We have called, emailed, escalated, and pushed until we got the right answer. Not because we had to — because that is what you deserve when you trust us with something as important as your vacation.
That is the part nobody sees. But I want you to know it happens every single day.
What We're Excited About Right Now
We are constantly learning, growing, and looking for ways to serve our clients better. A few things we're working on and excited about right now:
New supplier partnerships. We recently connected with a Europe ground operator offering completely custom, hand-built European itineraries — day-by-day, hotel by hotel, tailored to our clients' travel style. We are exploring this as a new tool to bring more personalized European travel to our clients. More on this soon.
Better client communication. We just finished a full review and rebuild of our automated reminder system. Every trip now gets the right pre-departure touchpoints — check-in reminders, dining reservation windows, excursion booking nudges, and more.
The Travel Lab Program. For those of you who have ever thought about becoming a travel advisor yourself, or know someone who has — our training and mentorship program is growing. We are building something really special there, and I am so proud of it. Check it out at TravelLabProgram.com and Parkland College.
A Note from Me, Personally
I started Island Travel Group 25 years ago because I believed — and still believe — that travel changes people. It opens your eyes, softens your edges, and gives you stories you tell for the rest of your life.
Every booking we make is part of someone's story. A honeymoon. A family reunion. A milestone birthday. A bucket list trip finally checked off. A retirement adventure. We know that. We feel the weight of it, and we take it seriously.
Thank you for trusting us with your travel. Truly.
We are here, we are working, and we are so glad you're along for the ride.
Ready to start planning your next chapter?
📞 Call or text: 217-202-3406 📧 Email: [email protected]
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