Today we’d like to introduce you to Dina Dennis.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I spent over 20 years in the healthcare education world leading sales teams, chasing big goals, and working with people all across the country. On paper, I was successful in sales — and yes, I loved being number one — but what really fueled me wasn’t the numbers. It was the service. I loved building relationships, noticing the little details, and making sure people felt truly taken care of.
After leaving healthcare, I opened a local boutique and café with a business partner. It was fun and creative, but once again, what I loved most were the connections with our customers. So when the chance came to step into travel planning, I felt an undeniable pull.
Now, I bring that same passion for service into every trip I design. A great vacation isn’t just about flights and hotels — it’s about knowing someone is in your corner from start to finish. My goal is to make travel seamless and memorable, so my clients can relax and just enjoy the journey.
At the end of the day, service is what drives me. Travel is simply the best way I know to share it — and I love every minute of it.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
No, not really. I became a travel planner in 2018 and spent most of that year just learning. In 2019, I finally got rolling and built up about half a million in travel. Coming from a world where the sales goals were huge, I still felt like I hadn’t hit where I wanted to be. Later, I realized that half a million in your first year is actually pretty strong.
Then 2020 came, and instead of planning trips, I was canceling and rebooking almost everything. It felt like all that work just disappeared. It was frustrating and exhausting, but it also showed me how much clients needed someone steady to walk them through it.
So no, the road hasn’t been smooth. But the bumps taught me a lot and made me better at what I do.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I’m a travel planner, and what I really love is creating custom trips. Cruises are part of what I do, but my passion is building unique itineraries — the kind that fit each client instead of a cookie-cutter package.
I book a lot of Italy and Ireland, along with Mediterranean cruises and river cruises. Those are the trips where I can dig into the details — finding the right balance of sightseeing, local experiences, and downtime so it actually feels like a vacation.
What I’m most proud of is the relationships I’ve built with my clients. They trust me to take their ideas, even if they’re just half-formed, and turn them into something real. And what sets me apart is the service. I don’t just book flights and hotels — I make sure every piece of the trip connects smoothly so my clients can relax and enjoy.
What’s next?
Right now, I’m part of a franchise, but I’m working on moving into my own franchise. The plan is to build it out and bring on a few new agents so we can offer even more specialized service to our clients.
My goal isn’t to be the biggest agency out there — it’s to be the best. I want every client to feel like their trip was designed just for them and that they were cared for every step of the way. Growing with the right people on my team will help make that happen.
Contact Info:
- Website: https://dinadennis.cruiselandandsea.com/
- Instagram: https://www.instagram.com/dinadennis/
- Facebook: https://www.facebook.com/cruiseplannersdinadennis
- LinkedIn: https://www.linkedin.com/in/dinadennis/
Image Credits
All of these photos are taken by me.
