About Ask A Captain

About Me

I’m Captain Scott C. Simpson, a 500-Ton Master with more than 3,000 days at sea and decades of hands-on maritime experience across Alaska, Hawaii, the Caribbean, and the East Coast. My career has spanned charter operations, commercial fishing, yacht brokerage, towing and recovery, maritime instruction, and safety management—giving me a deep, practical understanding of what makes vessels, crews, and operations run safely and efficiently.

I’ve captained vessels up to 130 feet, overseen full deck operations, trained crews, ensured passenger safety for groups of up to 80, and maintained strict compliance with USCG and SOLAS regulations. Whether managing complex charters, diagnosing vessel issues, interpreting tides and currents for precise navigation, or maintaining equipment to professional standards, my focus has always been on reliability, safety, and exceptional client experience.

Beyond the helm, I bring a strong background in business operations, from budgeting and planning to marketing, networking, and customer acquisition—skills sharpened during my years in state program management, construction inspection, and top-ranking pharmaceutical sales.

Today, I use this broad expertise to help boat owners, buyers, and operators make smarter, safer, and more informed decisions. Whether you're purchasing a vessel, improving operations, preparing for inspections, or optimizing charter performance, I offer guidance rooted in real-world maritime experience and a career built on professionalism, problem-solving, and a genuine passion for life on the water.

Take the stress, guesswork, and hidden risks out of boating with expert guidance from a licensed captain who knows boating and sailing waters inside and out. Whether you're buying your first boat, learning to dock with confidence, planning a safe trip down the ICW, The Great Loop, getting ready to do your first crossing, or just need honest answers before making an expensive decision, you’ll get clear, practical advice that saves you time, money, and frustration. I help new and experienced boaters avoid costly mistakes, build real skill on the water, and feel confident every time they grab the helm. If you’re ready to make smarter decisions and become a safer, more capable boater, book your consultation today and take control of your boating journey.

I’ve been on the water long enough to know one thing for certain:
Bad decisions in boating come from bad information.

People buy the wrong boat, take the wrong route, anchor in the wrong spot, or miss simple maintenance that turns into expensive breakdowns. My goal is to make sure that doesn’t happen to you.

Whether you’re buying your first boat, learning how to handle it, or planning a trip down the ICW, I’m here to help you make confident, smart choices every time you leave the dock.

• You talk directly to a real captain — no assistants, no bots, no fluff
• I tailor everything to your boat, your skill level, and your goals
• Local knowledge of St. Augustine, Jacksonville, Daytona, the  entire ICW and Caribbean waters.
• Straightforward, honest advice — even if it means telling you NOT to buy a boat
• No memberships required or hidden fees

Just reliable guidance, whenever you need it.