Cheryl Bailey

Crafting Unforgettable Travel Experiences

Cheryl Bailey has been passionate about travel for as long as she can remember, exploring breathtaking destinations like the Caribbean, Alaska, Iceland, and Europe. Her deep love for adventure and discovery naturally led her to a career as a travel agent, where she transforms her firsthand experiences into carefully tailored journeys for her clients. What began as helping friends and family plan vacations has grown into a fulfilling profession where Cheryl’s enthusiasm and expertise shine.

Specializing in cruises and Caribbean destinations, Cheryl is a master at curating memorable group trips, whether for Spring Break, weddings, or “friends” getaways. She thrives on the joy of helping groups create lasting memories together, designing experiences that cater to every type of traveler. From serene beach escapes to thrilling adventures on the high seas, Cheryl meticulously handles every detail so her clients can simply relax and enjoy.

What truly sets Cheryl apart is her unwavering dedication and thorough approach. She is an avid researcher, continually exploring new destinations, uncovering hidden gems, and staying up-to-date on the best excursions, accommodations, and travel tips. Her personal travels, often alongside her husband—he’s a gambler and she’s a beach lover—fuel her expertise. Together, they’ve embraced cruising as their perfect blend of relaxation and adventure, frequently traveling and discovering new ports of call.

Cheryl’s commitment to her clients goes beyond booking trips; she provides a concierge-level service that ensures a seamless experience from start to finish. One of her standout success stories involved a client with last-minute cruising needs. When the desired room category was initially unavailable, Cheryl’s persistence and determination led her to call the vendor daily until she secured the perfect accommodation. She also crafted a personalized list of excursions, one of which became the highlight of their trip. These moments of going above and beyond are what Cheryl thrives on, as they showcase her ability to turn challenges into triumphs.

Cheryl’s clients know they can count on her every step of the way. She provides expert guidance on pre- and post-cruise hotels, transfer arrangements, and excursion recommendations, while offering personal insights to ensure each trip feels unique and well-rounded. Her clients have direct access to her personal cell phone, allowing for quick assistance with any questions or concerns, whether they arise before departure or during the trip.

For Cheryl, travel is more than just a business—it’s about building lasting relationships. She loves hearing from clients while they’re on vacation, sharing in their excitement, and following up after their return to ensure every expectation was met. Cheryl’s passion for creating personalized, worry-free vacations and her genuine care for her clients make her an invaluable partner in crafting travel experiences that truly stand out.