Ask a Captain

Based in St. Augustine, Florida, Ask a Captain delivers professional maritime consulting and captain services to boat owners navigating the challenges of vessel ownership, operation, and maintenance along the Eastern Seaboard and beyond. Founded and operated by Captain Scott Simpson, a USCG licensed 500GRT Master, the service provides direct access to captain-level expertise for boaters who need trustworthy guidance on everything from pre-purchase decisions to advanced seamanship training.

The business specializes in pre-purchase consultations that help prospective buyers avoid costly mistakes before committing to a vessel. Captain Simpson conducts thorough vessel inspections and delivers candid assessments about condition, suitability, and potential issues—advice grounded in years of hands-on marine experience rather than sales incentives. For buyers new to boating or considering an unfamiliar vessel type, this independent evaluation can mean the difference between finding the right boat and inheriting someone else's expensive problems. Ask a Captain also offers boat handling instruction and captain training tailored to individual skill levels, from foundational seamanship to complex navigation and docking techniques in challenging conditions.

Route planning and navigation guidance represent another core offering, particularly valuable for cruisers preparing passages along the Intracoastal Waterway or tackling unfamiliar coastal waters. Captain Simpson draws on extensive knowledge of Northeast Florida's waterways—including tricky inlets, shifting shoals, and seasonal conditions—to help boaters prepare properly for extended cruises. The service extends to vessel management for owners who need reliable oversight and maintenance coordination, as well as professional delivery services for boats being relocated to new home ports. This breadth of capability makes Ask a Captain a versatile resource for vessel owners at every stage of the boating lifecycle.

What distinguishes the service is its streamlined, no-middleman approach. Clients communicate directly with Captain Simpson rather than navigating through assistants or automated systems. Each consultation is customized to the specific vessel, skill level, and objectives at hand, whether that involves evaluating a potential purchase in Jacksonville, preparing for a passage south along Florida's Atlantic coast, or developing competence with a newly acquired yacht. The focus remains squarely on practical, honest advice designed to keep boat owners confident and informed on the water.

Ask a Captain's regional expertise in Northeast Florida waters combines with a service model designed for flexibility across broader geographic areas. Remote consultations, travel-based inspections, and nationwide delivery capabilities allow the business to support clients well beyond its St. Augustine home base. As boat ownership continues attracting newcomers who lack access to reliable maritime mentorship, Ask a Captain occupies a valuable position in the market: providing professional captain services without the overhead or impersonal structure of larger marine operations.