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Matthew Bay
Burlington, KY Travel Agent
Wayward Traveling Co, an independent agent with WorldVia, a Travel Leaders Agency
5.0
(3)
100% Recommended
Matt and Amber made our cruise experience absolutely seamless. From helping us pick the perfect itinerary and ship to walking us through stateroom options, port excursions,... Read More >
Areas of expertise
Destinations:
Walt Disney World, Caribbean, Mexico, Universal Orlando, DisneylandInterests:
Disney Vacations, Honeymoons, Theme Parks, All Inclusive, CruisesSuppliers:
Disney, Virgin Voyages, Royal Caribbean, Universal Parks & Resorts Vacations, Sandals and Beaches ResortsAbout Me
Specialist in Disney, Cruises & All-Inclusive Tra
We specialize in creating unforgettable vacations to Disney destinations, all-inclusive resorts, and cruises around the world. Whether you’re visiting Walt Disney World for the first time with young children, sailing away on a romantic honeymoon cruise, or relaxing at a luxury beachfront resort, we handle every detail so you can focus on making memories. Our firsthand travel experience allows us to provide expert advice on choosing the right resort or ship, navigating Disney parks with ease, and selecting excursions and activities that match your style. We work with families, couples, and groups to craft personalized itineraries that blend must-do experiences with time to relax. From park reservations and dining at Disney, to arranging private shore excursions on cruises, to recommending the best all-inclusive resorts in the Caribbean and beyond, our goal is to make your vacation seamless, stress-free, and exactly what you’ve been dreaming of.
Areas of expertise
Destinations:
Walt Disney World, Caribbean, Mexico, Universal Orlando, DisneylandInterests:
Disney Vacations, Honeymoons, Theme Parks, All Inclusive, CruisesSuppliers:
Disney, Virgin Voyages, Royal Caribbean, Universal Parks & Resorts Vacations, Sandals and Beaches ResortsMy Travel Specialties
Personalized Travel for Families, Couples & Groups
▶Personalized Travel for Families, Couples & Groups
Hi, I’m Matt, and alongside my wife Amber, we’re the husband-and-wife duo behind Wayward Traveling Co. We’re proud Disney Vacation Experts — and parents of twin newborns — which means we know exactly what it takes to create a magical Disney vacation that works in the real world.
Our client...Read More ▶
Romantic Honeymoon Cruise Specialist
▶Romantic Honeymoon Cruise Specialist
Your honeymoon should be effortless, unforgettable, and tailored to your style as a couple. That’s why we love planning honeymoons aboard cruise ships, where every detail — from your stateroom view to your shore excursions — can be customized for you.
Whether you dream of sipping champagne...Read More ▶
Disney Vacations for Families & Groups
▶Disney Vacations for Families & Groups
As parents who have experienced Disney with toddlers, extended family, and everything in between, we understand the unique challenges and rewards of planning the perfect Disney vacation. Our favorite guests to plan for are families with young children visiting for the first time, and family group...Read More ▶
REVIEWS
Rating: 5.0
3 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 3 reviews
Our Dream Cruise—Perfectly Planned!
Reviewed By Cruisewithconfiedence - Louisville, KY | Traveled to Caribbean
Matt and Amber made our cruise experience absolutely seamless. From helping us pick the perfect itinerary and ship to walking us through stateroom options, port excursions, and even what to pack—they thought of everything. We felt so prepared and could truly relax and enjoy every moment. It was our first cruise, and we were a little nervous, but they made us feel confident and excited the whole way through. Their personal recommendations made a huge difference, and we’re already looking at booking our next sailing with them!
Matthew Bay responded
"You just made our day! We’re so happy you had an amazing first cruise and that we could help take the pressure off. Helping you feel confident and excited is exactly why we do what we do. Can’t wait to help you plan the next one—bring on the next adventure! ??"
✓ I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Stress-Free Disney Planning from Start to Finish!
Reviewed By DisneyFamily - Cincinnati OH | Traveled to Walt Disney World | Florida | USA
Planning a Disney vacation can be overwhelming, but Matt and Amber made it so easy—and actually enjoyable! They walked us through every step, from choosing the best resort for our family to helping us understand Genie+, dining reservations, and even park hopping. Their tips saved us time, money, and a lot of stress. We saw and did more than we ever thought possible, and our kids are still talking about the trip! If you want to experience the magic of Disney without the planning headaches, book with Matt and Amber. Truly a 5-star experience!
Matthew Bay responded
"Thank you so much for the kind words! We loved helping you plan such a special trip and are so glad everything came together perfectly. It means the world to us that you felt cared for every step of the way. We can’t wait to help you plan the next adventure—wherever it may take you!"
✓ I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
The best trip of our lives!
Reviewed By HappyTravelers23 - Lexington, KY | Traveled to Ocho Rios | Jamaica | Caribbean
From the very beginning, Matt and Amber made the entire planning process smooth and stress-free. They really took the time to understand what we were looking for and recommended options we never would’ve found on our own. Every detail—from flights and resort bookings to excursions—was perfectly thought out and organized. We felt taken care of the whole way through, and it was clear how much pride they take in making sure their clients have the best experience possible. We can’t wait to book our next adventure with them!
Matthew Bay responded
"Wow—thank you so much! It means the world to us that you felt taken care of every step of the way. We’re so glad everything came together and that you had such an amazing trip. Can’t wait to help you plan the next one—let’s make it even better! ????"
✓ I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Certifications & Awards

Celebrity Learning Certification
AMResorts Master Agent

Princess Commodore Certified

Royal Caribbean University - Bachelor of Adventure

Royal Caribbean University - Master of Adventure
My Places
When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.
My Photo Albums and Videos
?? Our Engagement Trip: A Magical Disney Moment
View Album
Disney World
View Album
Client Testimonials
Disney First Timers
Amber & Matt made our first Disney trip stress-free! They handled every detail from park tickets to dining, so we could just enjoy the magic.
Sarah Whitman – Columbus, OH