Hi, I'm
Kayla Matthews
FAMILY VACATION SPECIALIST
Based in Rochester, NY
I’m Kayla Matthews — a passionate, detail-driven travel advisor with a love for creating unforgettable vacation experiences for families, couples, and adventure-seekers alike. With a strong background in creative business ownership and customer service, I bring a personal, hands-on approach to every trip I plan. Whether you’re dreaming of a Disney getaway, a tropical escape, or a custom-crafted cruise, I’ll handle the planning so you can focus on the fun. Let’s make your next adventure easy, magical, and stress-free!
Let's Get Started
Kayla's Travel Story
Every advisor has a story. Here's a look at the trips, places, and people that shaped how Kayla plans yours.
What I Include in My Planning
Here's what's part of every trip I book. Have a special request? Just ask — I love to tailor things to your family.
- Custom itinerary planning
- Park strategy & Lightning Lane guidance
- Ongoing price monitoring
- Day-of trip support
- Group / multi-family coordination
- Celebration planning (birthdays, anniversaries, honeymoons)
- Booking changes & advocacy
- Ticket & resort recommendations
- Dining strategy & reservations
Working with Kayla
Share Your Vision
Tell Kayla who's traveling, when, and what makes a vacation feel magical for your family.
Get a Custom Plan
Receive personalized resort, cruise, or destination options curated to fit your style and budget.
Travel Worry-Free
From booking to boarding pass, you'll have an expert in your corner the entire journey.
What does Kayla specialize in?+
Does it cost extra to book with Kayla?+
How quickly will Kayla respond?+
Where is Kayla based?+
Your Dream Trip Starts Here
Tell Kayla about your vacation vision. Pick the path that feels easier — chat it out or fill the form.
Prefer to chat instead?
Have a quick conversation with Kayla's assistant. Same questions as the form, but easier — and you can ask anything along the way.
Prefer to reach out directly? kayla.matthews@cupcakecastlestravel.com
Trusted & Accredited
© 2012 - 2026 CCTC Travel Group, LLC. All rights reserved.
CCTC Travel Group, LLC is registered with the following state licenses: Florida Seller of Travel Registration No. ST42417, California Seller of Travel Registration No. 2143399-40, Washington Seller of Travel Unified Business ID (UBI) # 604 562 798. All Disney artwork, logos and properties © Disney. Ships Registry: The Bahamas.
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