Hi, I'm
Kelly Gray
FAMILY & VACATION SPECIALIST
Based in Hastings, Florida
"Because the best memories are made when you travel together."
Hi, I’m Kelly, a Florida-based travel advisor who specializes in family adventures to destinations like Disney, Universal, and cruises. As a mom of three sons—teenagers to adults, including one married
I understand what families need for a smooth, enjoyable getaway. I bring firsthand experience and attention to detail to every trip I plan. My goal is to create personalized, seamless, and meaningful itineraries. I love helping families explore amazing destinations and make lasting memories together. Let’s create a memorable vacation for you.
Let's Get Started
Kelly's Travel Story
Some of my favorite trips are the ones that brought my family together and created unforgettable memories. I’ve enjoyed visiting my son in Sacramento and exploring San Francisco, experiencing the culture of New Orleans, and relaxing in Key West. My first NCL cruise to the Bahamas was memorable, and I also love frequent trips to Disney. Traveling has taught me the importance of slowing down.
Favorite Places
Certifications & Training
Certifications
- College of Disney Knowledge
- Universal Destinations & Experiences Graduate
- Carnival Cruise Line Travel Professional
- Royal Caribbean Travel Professional
- Celebrity Cruise Line
- Virgin Voyages First Mate Certified
- Sandals & Beaches Resort Travel Certified
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.
- Park strategy & Lightning Lane guidance
- Ongoing price monitoring
- Day-of trip support
- Booking changes & advocacy
- Pre-trip prep call
- Ticket & resort recommendations
- Dining strategy & reservations
- Custom itinerary planning
Working with Kelly
Share Your Vision
Tell me 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 Kelly specialize in?+
Does it cost extra to book with Kelly?+
How quickly will Kelly respond?+
Where is Kelly based?+
Your Dream Trip Starts Here
Tell Kelly 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 Kelly's assistant. Same questions as the form, but easier — and you can ask anything along the way.
Prefer to reach out directly? kelly.gray@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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