My Sojourney Story: Caitlin Bailey

Tell us a bit about yourself. Why did you become a travel advisor?

I became a travel advisor because of my passion for travel and my enjoyment in planning extensive family vacations. Realizing I could turn this passion into a career, I embraced the opportunity to help others experience amazing vacations while continuing to explore new destinations myself. It brings me great joy to hear that my clients had a wonderful time on their trips, knowing that I played a part in creating those memorable experiences. 

What do you enjoy most about being a travel advisor?

What I enjoy most about being a travel advisor is visiting new destinations and exploring the world firsthand. This allows me to craft personalized vacation experiences for my clients with the assurance that I have personally vetted these locations, ensuring they can have peace of mind knowing that their travel plans are informed by my own experiences. 

What destinations do you specialize in, and what draws you to those particular places?

I specialize in romance and family travel, focusing on destinations like all-inclusive resorts in the Caribbean, ocean and river cruising, Hawaii, Disney, and Universal. My personal love for the beach and the sun deeply influences my specialty choices; I'm drawn to places that offer the warmth and relaxation of a beach setting. I particularly enjoy planning romantic getaways—be it for weddings, honeymoons, anniversaries, or couples’ retreats—as these are experiences I cherish in my own life with my husband. Additionally, having two small children, I am well-versed in creating memorable family vacations, especially those involving theme parks and roller coasters. Hawaii is a favorite because it combines a lush, tropical paradise with the conveniences and security of being in the United States, offering a variety of experiences from beach relaxation to adventure activities. 

Is there a moment from your travels that has impacted the way you approach travel advising?  

Yes, a recent travel experience significantly impacted how I approach travel advising. During a family vacation, we tried to visit three different parks in a short period, but a lack of detailed information from the supplier led to missed discounts and unnecessary stress. This experience underscored the importance of being thoroughly informed about the destinations I recommend.  Now, I make sure that I personally visit as many destinations as I can, consult with my fellow Sojourney Travel advisors, and conduct thorough research. This approach ensures that I provide the most accurate and comprehensive information to my clients, helping them enjoy a seamless and enjoyable vacation experience. 

What advice would you give to travelers looking to plan their next vacation?

My advice to travelers looking to plan a vacation would be to first identify where you're interested in visiting or what experiences you're looking to enjoy, consider your budget, and think about the level of service you desire during your trip. Then, reach out to your preferred Sojourney Travel Advisor, like myself, to help craft your next unforgettable vacation. At Sojourney Travel, we leverage our personal travel experiences and established relationships with trusted suppliers to deliver excellent products and customer service. We not only save you time by doing the research for you, but we also strive to secure the best prices and sometimes even exclusive perks that aren't available when booking directly. Booking with a Sojourney Travel Advisor truly pays off.

What do you enjoy most about working with clients to plan their trips? 

I love interacting with new people and helping them create stress-free vacation experiences where they can simply show up and enjoy themselves. I see vacations as a crucial investment in one's wellbeing, and I'm passionate about ensuring my travelers get the best possible deal, often with exclusive perks that make their trips extra special. There's a personal joy I find in looking forward to my own vacations, and it amplifies my happiness when I can help others make the most out of their hard-earned vacation money. 

Can you share a memorable travel experience or a unique destination that left a lasting impression on you?  

One of my most memorable travel experiences was a trip to Maui, Hawaii, in December 2023, following the wildfires in Lahaina earlier that fall. Despite the recent devastation, the island's unaffected areas remained breathtakingly beautiful, showcasing the resilience and enduring beauty of Maui. I stayed in a local resort in Kaanapali that housed many locals affected by the fires. The warmth and kindness of the staff and residents were incredibly heartening; everyone I met had a great big smile and an indomitable spirit, radiating hope and joy despite their recent hardships. This unique atmosphere of 'Aloha,' a deep-seated sense of love and community, was palpable everywhere I went. Additionally, I participated in a land conservation project, contributing positively to the island’s recovery. This trip left a profound impact on me, illustrating the powerful connection between people and place, and it's an experience that I cherish deeply and look forward to revisiting. 

What destinations or experiences are on your personal travel bucket list?  

Some of the destinations and experiences on my personal bucket list include enjoying a river cruise through Europe, chartering a yacht in Croatia, visiting Australia to see family and explore popular sites, and traveling to Scotland. Additionally, I'm looking forward to experiencing the exotic allure of Bali, Indonesia, and the Maldives. I also have plans to visit Caribbean gems like Aruba, Curacao, Barbados, and St. Vincent and the Grenadines. Another dream experience of mine is to soak in the festive spirit at the Christmas Markets across Europe. These diverse destinations and experiences reflect my deep passion for exploring different cultures and landscapes around the world. 

What is a fun fact about you that your clients may not know?  

A fun fact about me that my clients may not know is that although I'm usually quite reserved, I occasionally enjoy singing karaoke. Despite feeling very nervous about performing, there's one song I always brave up to sing: "I Love Rock and Roll" by Joan Jett. It's a moment where I step out of my usual quiet demeanor and share a bit of fun and rock-n-roll spirit!