Your travel advisor
Meet Kelly Gray
Personal vacation planning for Disney trips, cruises, and all-inclusive getaways — with someone who genuinely cares about getting it right.
Planning a vacation should feel exciting, not overwhelming. But between resort options, park tickets, dining reservations, cabin categories, and itinerary choices, it's easy to spend hours researching and still feel uncertain. That's where Kelly comes in.
Kelly is a personal travel advisor based in Hastings, Florida, working as part of Cupcake Castles Travel Co. She specializes in the kinds of vacations that take real planning — Disney World, Disney Cruise Line, ocean cruises, and all-inclusive Caribbean resorts — and she works with families, couples, and groups across all 50 states.
Her job is to understand what you actually want from a trip, match you with the right options, and handle the details so you can focus on looking forward to it. There are no fees for her planning services — she's compensated by the travel suppliers, which means her help costs you nothing extra.
What working with Kelly looks like
She listens first
Before recommending anything, Kelly asks about your travel style, your group, your budget, and what matters most to you. A family with young kids planning their first Disney trip has very different needs than a couple celebrating an anniversary on a cruise.
She knows the options
Disney World alone has over two dozen resort hotels, multiple ticket types, and a dining reservation system that opens 60 days in advance. Cruise lines each have their own ship categories, cabin types, itineraries, and onboard experiences. Kelly helps you navigate that without having to become an expert yourself.
She handles the logistics
Once you decide on a direction, Kelly takes care of the booking details — and stays available through the planning process if questions come up or plans change.
No fees, ever
Kelly's planning services are complimentary. Travel advisors are compensated by the suppliers — resorts, cruise lines, and vacation packages — not by charging clients extra. You get personalized help at no additional cost.
What Kelly specializes in
Disney Vacations
Walt Disney World, Disneyland, and Disney Cruise Line — resort selection, ticket planning, dining strategy, and itinerary help for first-timers and returning guests alike.
Ocean Cruises
Cruise line selection, ship and cabin guidance, itinerary comparison, departure port logistics, and family vs. adults-only considerations across major cruise lines.
All-Inclusive Resorts
Caribbean all-inclusive planning — adults-only vs. family resorts, destination selection, room categories, honeymoons, anniversaries, and destination weddings.
Training and affiliations
Kelly has completed training programs offered by travel suppliers and industry organizations. Her verified credentials include:
- Virgin Voyages Sailing Specialist — Completed Virgin Voyages' advisor training program.
- Cupcake Castles Travel Co. — Licensed travel agency — FL ST42417 · CA 2143399-40 · WA UBI 604 562 798
- CCTC Travel Group, LLC — Operating entity for Cupcake Castles Travel Co.
Credentials listed reflect verified training completions. Kelly does not claim Disney-specific designations, Sandals/Beaches certifications, or other supplier credentials not listed here.
Ready to start planning?
Tell Kelly about your trip and she'll put together options tailored to you.
Travel With Kelly is a personal travel advisory service operating under Cupcake Castles Travel Co. (CCTC Travel Group, LLC). Kelly Gray is an independent travel advisor affiliated with this licensed agency. This site is not affiliated with, endorsed by, or sponsored by The Walt Disney Company, Disney Parks, or any cruise line or resort brand referenced herein. All trademarks are the property of their respective owners.