I'm Jessica Clayton- founder of Humdinger Travel and your go-to travel curator. At Humdinger Travel, we specialize in luxury travel planning, unforgettable cruises, and expertly curated group trips. Founded on a passion for creating seamless, elevated experiences, I help travelers discover the world in style. With personalized attention to detail, insider knowledge, and a commitment to exceptional service, I take care of the details so you can focus on the magic. Because epic vacations should be easy. From solo luxury escapes to hosted group getaways—we plan, you play. Worry-free travel with no stress, just stories you’ll tell forever!
Curating elevated luxury adventures, I design seamless journeys that blend sophistication, comfort, and unforgettable experiences for those seeking more than just a vacation.
I can book your dream vacation on any cruise line you choose, ensuring you get the best options, perks, and value. With an agent by your side, you’ll enjoy expert guidance, personalized recommendations, and stress-free support from planning through sailing—so you can focus on making memories at sea.
Humdinger Adventures was founded on the art of expertly crafting group trips that cater to a wide range of personalities and travel styles. Whether it’s a getaway with friends, a family adventure, or a corporate retreat, we excel at creating seamless, memorable experiences that everyone can enjoy together.
Dec 13-21, 2025
Get ready for 8 days in paradise with the perfect balance of fun, freedom, and pura vida vibes. Whether you're set on surfing from sunrise to sunset, taking off on an ATV Adventure through the jungle, or just want to sip a cold drink with your toes in the sand- this trip is for you!
August 2026
Set sail with us in 2026 on an unforgettable Virgin Voyages group trip out of Miami! Experience adults-only luxury at sea with world-class dining, incredible entertainment, and stunning Caribbean destinations—all while traveling with a fun, like-minded group. Secure your spot today and let’s make memories together!
Jul/Aug 2028
Join us to cheer on the USA in the 2028 Summer Olympics in Los Angeles followed by 2 weeks in Hawaii! You can join us for just LA, just Hawaii, or go big and do both!
I have two ways to get started!
- My "Getting Started Questionnaire" if you do better organizing your ideas before we talk.
- Schedule a call with me if you do better chatting through your ideas first!
Honoring family, fueled by passion, and crafted with care—your travels deserve more than ordinary.
At Humdinger, travel isn’t just about going places—it’s about creating unforgettable moments that feel perfectly you.
I’m Jessica Clayton, founder and travel curator. My journey into this business began long before Humdinger Travel had a name. For years, I planned trips for myself, my family, and friends. The adventures we shared left such an impression that before long, people were asking me to plan their future travels too. From intimate getaways to large group trips, I discovered that I loved every detail of crafting experiences that made travel stress-free and unforgettable.
What began as a passion quickly became a calling, and Humdinger Travel was born. The name is deeply personal: my grandfather, Neil Clayton, used to call me his Humdinger. He worked tirelessly to give his children and grandchildren more opportunities than he had, and his example inspires me every day. Naming my company after him is both an honor and a reminder—to put in the work, to care deeply, and to make every trip something truly special.
When you work with me, you’re not just booking a vacation—you’re gaining a travel partner who takes the time to understand your style, your dreams, and the little details that make a trip unforgettable. The more we work together, the more tailored your experiences become. My goal is to take away the anxiety of planning so you can simply tell me what you imagine—and I’ll find a way to make it happen.
Because you don’t just want any trip.
You want a Humdinger.