Professional Captain Services, Management and Delivery
Avoid Costly Boating Mistakes — Get Expert Captain Guidance Before You Buy, Launch, or Leave the Dock.”
About Ask a Captain
My Story
Hi! My name is Scott Simpson, I’m a USCG licensed 500GRT Master, with years of real-world experience running boats, teaching new owners, inspecting vessels, and helping people stay safe on the water. I started this service with one mission:
Make boating easier, safer, and far less expensive for everyday boaters.
Boating should be enjoyable — not stressful, confusing, or full of costly surprises. Too many new boat owners rely on random forum advice, unqualified opinions, or salespeople who don’t always have their best interests in mind. I wanted to offer something better: real captain-level guidance you can trust.
Why I Do This
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.
What Makes This Service Different
- 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, and the ICW
- 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.