Originally from Freeport in Midwest, Michigan, AJ has been with Sebago (since 2020) for over two years. Before joining Sebago, AJ was a captain with our sister company, Cruz Bay Watersports in the US Virgin Islands. The Power Adventure is AJ’s favorite trip because “it’s like a charcuterie board – you get everything in one package.” AJ also lived in Australia for a few years and now enjoys his home life in Key West with his wife and daughter.
Originally from Holmes Beach, Florida, Jim has been with Sebago (since 2011) for 11 years. Jim manages the day-to-day captain and crew operations as well as driving the catamarans and working the check-in sales kiosk. Jim’s favorite trip is the Island ‘Ting because it’s a mellow day on the water and he loves the aquatic life in the mangroves. When not working he enjoys spending time with his wife and their dogs, his aquarium, and fishing.
Originally from North Carolina, James moved to the Keys in October of 2014 following a three-year deployment in Afghanistan working for a defense contractor. He has been with Sebago since 2016, working as a captain for four of those years and now as Sales Manager. He enjoys all of our trips, but his favorite would be the Land’s End Sunset Sail for the live music. James met his wife at Sebago, and they both enjoy the large selection of great dining that Key West has to offer when they aren’t traveling.
Chloe is originally from Boston, Massachusetts and has been in Key West (since 2013) for 9 years, and joined Sebago in 2016 and is our office/retail manager. Chloe has enjoyed a career singing professionally in Key West and loves to travel. Her favorite of our tours is Land’s End Sunset Tour where she can sing along with some of Key West's favorite musicians while sipping cocktails, eating delicious appetizers, and enjoying our breathtaking sunsets. Chloe also loves spending time exploring Key West’s cuisines with her husband and long drives in her Jeep with her mini–Australian Shepherd, Ollie.
DIRECTOR OF SALES AND MARKETING
Originally from Boca Raton, Florida, Courtney has been in Key West and with Sebago (since 2005) for 17 years. She manages Sebago’s private charters and events, concierge desks, and local marketing for Sebago. Her favorite Sebago trip is the Land’s End Live Music Sunset Sail—the best combination of a beautiful Key West Sunset & happy hour. Courtney and her husband, also run a charter fishing business. When not working, Courtney enjoys fishing or relaxing at a sandbar with friends and her rescue dog, Daisy.
Kelley is from a small town in southern Michigan. She has been in Key West since 2020 and with Sebago since the Summer of 2021. Kelley’s favorite Sebago adventure would have to be parasailing, where you get an entirely different, and peaceful, view of paradise, although she also loves the Land's End with friends and seeing our spectacular Key West sunsets. When not working, she loves visiting her three kids back in Michigan, meeting new people, and spending time with her husband exploring this incredible place they get to call home.
VICE PRESIDENT OF OPERATIONS
Originally from McLean, Virginia, Jason has lived in South Florida since 2016, which serves as his home base to support Sebago and access RED Hospitality and Leisure’s other markets in Key Largo, St. Thomas, St. John, and Turks and Caicos. Jason is responsible for the overall Financial Performance, Employee Engagement, Guest Satisfaction, Hotel Relationships, Business Development, and Operational Execution of the company’s business units. His favorite Sebago trip is aboard the 37’ Axopar, enjoying the complete customization and luxury experience our local captains offer. The intimate experience and ability to learn something new about our marine life and the beautiful habitat surrounding the Keys makes it a unique experience you can only get with Sebago. Jason has an eight-year-old German Shepherd and enjoys spending time at the beach and dining in local restaurants with his girlfriend.
VICE PRESIDENT OF ACCOUNTING & FINANCE
Kendall leads RED’s finance and accounting team across all current business markets. Kendall previously worked for Sebago Watersports (now RED’s Key West subsidiary) before starting her career in public accounting. In her public accounting tenure, Kendall honed her expertise in financial statement and employee benefit plan audits, reviews, compilations, and M&A purchase price allocation. Upon RED’s 2019 acquisition of Sebago, Kendall was excited to make the full-circle move back to Key West and to the hospitality/tourism industry which is a passion of hers.