Hi, I’m Courtney Schomburg, a Travel Advisor with Wanderly Adventures. I feel most alive when I’m traveling, exploring new places, learning about different cultures, and discovering the small details that turn a trip into a story you tell for years. That love of travel is the reason I do this work, and it’s what I bring to every itinerary I build.

Before joining Wanderly Adventures, I spent over 16 years building and running my own company, Pink Pineapple Properties, a short-term rental property management business here in Sarasota. Through that work, I’ve connected with guests from all over the world, helping each of them find the perfect rental and feel at home the moment they arrive. That work required an eye for detail, high standards, and a genuine dedication to every guest I served. I bring that same standard to travel planning. And although I’m a new travel advisor, I’ve already completed a range of destination certifications, including Atlantis Ambassador, Greece Specialist, Aruba Expert, Costa Rica Specialist, and more. I have high expectations for the hotels, restaurants, and cruises I recommend, because I only want to send my clients somewhere I’d be excited to go myself.

My passion for travel isn’t just professional. It’s personal. My 13-year-old daughter, Olive, made it her mission to visit all 50 states before she turns 21, and I’ve made it my mission to help her get there. That family goal has taken us across the country and shaped how I think about travel: it should be memorable, meaningful, and worth the journey. Whether it’s a milestone family vacation, a bucket-list cruise, or a weekend adventure to check another state off Olive’s list, I love helping clients create experiences they’ll talk about for years to come.

When I’m not planning trips, you’ll usually find me at the beach in Sarasota with my husband and business partner, Jon, and Olive, or out on Siesta Key volunteering with Turtle Patrol, one of my favorite ways to give back to the community I call home.

I can’t wait to help you plan your next adventure! Reach out anytime at CourtneyS@WanderlyAdventures.com and let’s start creating memories that will last a lifetime.