Multi-Destination & Experiential Travel Specialist

Sunrises while flying are always breathtaking!

Hi, I’m Kaitlyn Chance, the travel advisor and founder behind Wander with Kaitlyn, proudly affiliated with Wanderoso Travel Network. Based just outside of Montgomery, Alabama, I’m passionate about helping travelers turn their dream vacations into meaningful, stress-free experiences that become lifelong memories.

My journey into travel began long before I became a professional advisor. So far, I’ve explored 46 U.S. states, over 20 national parks, and seven countries, from staying at all-inclusive resorts throughout the Caribbean to road-tripping across the American West — and there are still so many more places on my list to see. Those adventures have taught me that travel is more than just a getaway — it’s a chance to reconnect with yourself, your loved ones, and the world around you.

I specialize in custom travel planning for all types of wanderers — from families seeking magical theme park vacations, to couples dreaming of romantic all-inclusive escapes, to adventurers craving epic national park road trips and cruise experiences. Whether it’s your first cruise, a milestone celebration, or a bucket-list expedition, I’ll handle the details so you can focus on creating the moments that matter most.

Before becoming a full-time travel advisor, I spent nearly a decade in education and instructional design. That background taught me how to truly listen, ask the right questions, and create experiences that fit individual learning styles — skills I now use to craft personalized, well-organized itineraries tailored to each client’s unique travel personality. My clients know me for my attention to detail, communication, and passion for creating seamless, worry-free experiences from start to finish.

As a lifelong learner, I’ve earned numerous certifications and continue to grow my expertise to serve clients with confidence and creativity:

• Disney College of Knowledge Graduate
• Royal Caribbean “Master of Adventure”
• Carnival Diamond Graduate
• Virgin Voyages Gold First Mate
• Sandals & Beaches Certified Specialist
• Iberostar Hotels & Resorts Certified Advisor
• Celebrity Cruises Certified Travel Advisor
• Universal Studios Graduate
• And more!

My travel philosophy is simple: travel should be personal, purposeful, and full of wonder. Whether you’re planning a relaxing resort getaway, an immersive cultural journey, or an adventure that takes you off the beaten path, I’m here to make the process effortless and enjoyable. Every itinerary I design is guided by your travel goals, style, and budget — with transparent communication and thoughtful touches throughout the process.

When you work with me, you can expect:

• A friendly consultation where I get to know your travel dreams and preferences
• Customized trip options tailored to your vision and budget
• Seamless coordination of details, including accommodations, transfers, excursions, and insurance
• Ongoing support before, during, and after your trip, so you’re never alone in the process

Travel has been a constant source of healing, inspiration, and joy in my life. It has helped me see the beauty in slowing down, exploring intentionally, and making every journey count. That’s what I strive to bring to every client I serve — not just a trip, but a collection of moments that stay with you long after you’ve unpacked your bags.

When I’m not designing dream vacations, you can find me hiking new trails, taking landscape photos, or spending time with my pets — my sweet dog Scout and two cats, Oliver and Macy — who love to keep me company while I plan your next adventure.

Let’s start planning your next great adventure — because when you wander with Kaitlyn, a Chance truly becomes a memory.