Originally from Freeport in Midwest, Michigan, Aj has been with Sebago for over two years. AJ has prior captain experience from 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 has also lived in Australia for a few years and now enjoys his home life in Key West with his wife and one-year-old daughter.
Originally from Holmes Beach, FL Jim has been with Sebago for 11 years. Jim manages the day-to-day captain & crew operations as well as drives the catamarans and also works in the check-in sales kiosk. Jim’s favorite trip is the Island Ting because it’s a mellow day on the water and loves the aquatic life in the mangroves. When not working he enjoys spending time with his wife and their dogs, aquarium keeping, and fishing.
Originally from NC, James moved to the Keys in October of 2014 following a three-year deployment in Afghanistan working for a defense contractor and has been with Sebago Watersports since 2016. Working as a captain for four of those years and now Sales Manager, he enjoys all of our trips, but his favorite would be the Lands End sunset sail for the live music. After meeting his wife at Sebago, 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 MA and has been in Key West for 9 years. Chloe has been with Sebago for 6 years and works as the office/retail manager. She has enjoyed a career singing professionally in Key West and loves to travel! Chloe most enjoys Sebago’s Lands’ End where she can sing along with some of Key West's favorite musicians while sipping cocktails, eating delicious appetizers, and enjoying Key Wests’ breathtaking sunsets. Chloe also loves spending time exploring Key Wests’ 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 Sebago for 17 years. Courtney manages the private charters & 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 she enjoys time 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 summer 2021. Kelley’s favorite Sebago adventure would have to be parasailing, where you get an entirely different view of the incredible island and it is so peaceful, although she also loves the Land's End with friends and seeing our incredible Key West sunsets. When not working, she loves to visit our three kids back in Michigan, meet new people and spend time with her husband exploring this incredible place we are lucky enough 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 expertise in financial statement & 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.