
Blaine Kubesh
Captain Blaine Kubesh
Captain Blaine Kubesh brings an adventurous spirit, extensive technical expertise, and a genuine passion for hospitality to every charter. A licensed U.S. Coast Guard Captain, RYA Yachtmaster Offshore, PADI Open Water Scuba Instructor, and airplane pilot, he has spent much of his life exploring—by sea, beneath the surface, and in the air.
Blaine’s love of sailing began at the age of ten and was further inspired by a close family member who circumnavigated the globe. Since then, he has sailed extensively throughout the Caribbean and Mediterranean, developing particular knowledge of the Leeward and Windward Islands. Now in his eighth charter season, he has captained hundreds of successful charters, creating thoughtfully planned itineraries that balance adventure, relaxation, and authentic island experiences.
Whether guests are looking to discover vibrant reefs, enjoy world-class snorkeling and diving, fish for dinner, explore scenic hiking trails, visit lively beach bars, try watersports, or simply unwind in a secluded anchorage, Blaine enjoys tailoring each charter to their interests. His local knowledge, calm professionalism, and guest-focused approach allow every voyage to feel seamless, personal, and unforgettable.
Before pursuing a full-time career in yachting, Blaine grew up on a farm and ranch in Montana before spending more than 20 years working in electrical and software engineering and cybersecurity. That background instilled a practical, safety-conscious mindset and exceptional attention to detail, while his Montana upbringing shaped the strong work ethic, easygoing personality, and appreciation for the outdoors that guests quickly come to appreciate.
Blaine especially enjoys introducing guests to the underwater world, sharing stories about the islands, organizing fun activities both on and off the water, and serving up a freshly caught fish after a successful day of fishing. Above all, he loves meeting new people and helping guests leave feeling they’ve truly experienced the Caribbean—not simply visited it.



























