Ask a Captain
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Professional Captain Services, Management and Delivery

Professional Captain Services, Management and DeliveryProfessional Captain Services, Management and DeliveryProfessional 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 licensed captain 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.

A luxury yacht sails on clear turquoise waters near a green shoreline.

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.

Learn More

Services / Price List

Consultations

Virtual / Phone consultations

Quick Captain Consult

49

30 minute phone or video session for simple questions, gear advice, problems, or navigation basics.

Full Consult

99

60-minute deep dive into trip planning, route guidance, weather concerns, safety, systems, or boat-buying guidance.

Boat Buying Support

Avoid Costly Mistakes & get expert evaluation

Listing Evaluation

129

Full breakdown of price, condition, red flags, repair estimates, and negotiation angles.

Man waving from a yacht's cockpit with a woman beside him under a clear sky.

Buyer Guidance Package

199

Includes 3 listing evaluations + 30-min call + checklist + negotiation plan.

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In-Person Services

Yacht/Vessel Delivery

$1000/Day for Captain & 1 Crew

(depending on vessel size and complexity)

Includes:

  • Licensed captain/crew
  • Route, tide, and weather planning
  • Daily progress updates
  • Pre-departure and arrival reports

Additional Costs (clearly disclosed):

  • Fuel
  • Dockage
  • Meals
  • Travel expenses

No surprises. No vague estimates.

Book Now

Yacht/Vessel Management Services

Starting at $350/month
(Final pricing based on vessel size, systems, and usage frequency)

Includes:

  • Scheduled onboard inspections
  • Safety and compliance checks
  • Maintenance coordination
  • Condition reports with photos
  • Pre- and post-trip readiness checks

Optional Add-Ons:

  • Storm preparation oversight
  • Vendor presence during repairs
  • Monthly sea trials
  • Detailed seasonal reports

Book Now

On-Water Training In YOUR boat!

$150/hr - 2 hour minimum

Overview:
Hands-on, practical training aboard your boat (preferred) or my training boat, focusing on docking, close-quarters handling, anchoring, and safety drills.

Who it’s for:
Owners who want confidence at the helm, couples sharing helm duties, or anyone preparing for longer trips or tighter marina situations.

What I do (step-by-step):

  1. Pre-session questionnaire to assess skill level, boat specs, and desired learning outcomes.
  2. Arrive on time with a clear lesson plan (we confirm weather and tide window).
  3. Warm-up: boat checks, safety briefing, and demonstration.
  4. Hands-on practice: docking approaches, engine/steering control, pivot turns, crab-walking with wind/current, anchoring drills, man-overboard drill if requested.
  5. Debrief: strengths, weaknesses, and a targeted practice plan.

Book Now

New Owner Coaching & Boat Orientation

$250 - 2.5 hours

Overview:
A comprehensive systems walkthrough for new owners: learn your boat’s systems, routine maintenance, safety checks, and emergency procedures.

Who it’s for:
Anyone who recently purchased a boat or inherited one and wants to understand how it operates and how to keep it seaworthy.

What I do (step-by-step):

  1. Pre-session intake: make/model, known issues, and owner questions.
  2. Onboard walkthrough: electrical (battery banks, shore power, breakers), fuel system, bilge pumps, sanitation (if present), steering, engine/drive basics, navigation electronics, and safety gear placement.
  3. Demonstrations: starting/stopping procedures, emergency shutoffs, and routine maintenance tasks (fuel/water filters, battery checks).
  4. Create a customized owner maintenance checklist and seasonal schedule.

Book Now

In-Person Services

Trip Planning & Route Management

$250

Who it’s for:
Cruisers, weekenders, or first-time ICW travelers who want a safe, timely, and enjoyable route.

What I do (step-by-step):

  1. Intake: origin, destination, vessel specs (draft, cruising speed), desired pace, and date range.
  2. Research: tides, bridge schedules, fuel availability, recommended anchorages, marinas, hazards, and local notices to mariners.
  3. Produce a route plan with timing windows (based on tide and bridge ops), ETA projections, and alternative stops.
  4. Include specific local tips (shoaling hot spots, recommended phone numbers, fuel docks with pump-out, preferred marinas).

Book Now

Pre-Survey Captain Companion

$350 

Overview:
An on-site (or dockside) captain’s inspection prior to a formal marine surveyor visit to identify obvious failures, take-aways, and dealbreakers so you don’t waste survey dollars.

Who it’s for:
Buyers who want a captain’s practical check before committing to a paid survey.

What I do (step-by-step):

  1. Meet at the boat (in water or on a trailer) with seller present (if applicable).
  2. Perform practical checks: engine start/run, compression checks (if possible), steering play, hull soft spots probe, battery condition check, visual electrical inspection, bilge inspection, and trailer condition.
  3. Provide immediate verbal feedback and a detailed written report with photos.

Book Now

Monthly Memberships

Boater Hotline Membership - $39/month

Overview:
Ongoing access for basic, rapid advice via text/email plus discounts on paid services.

Who it’s for:
New owners or seasonal boaters who want confident, on-hand answers without booking individual calls.

What it includes:

  • Unlimited simple questions via email/text (response within 48 hours).
  • 10% off consultations and in-person sessions.
  • Access to member-only monthly tip email.

Deliverables:

  • Email receipts of advice exchanges and member resources.
  • Price: $29/mo; cancel any time.
    Cancellation/Refund: Pro-rated refunds not provided; cancel to avoid future charge.


Book Now

Premium Membership - $79/month

Overview:
Full support package for owners who want proactive planning, priority access, and a monthly check-in.

Who it’s for:
Frequent boaters, liveaboards, or owners who value proactive maintenance and planning help.

What it includes:

  • Everything in Boater Hotline.
  • One 30-minute monthly consultation (call/video).
  • Priority scheduling for in-person sessions.
  • 20% discount on Pre-Survey and On-Water Training.
  • Priority route tweaks and trip planning support.

Deliverables:

  • Monthly 30-minute session notes and action items.
  • Expedited email response (within 24 hours).

Price: $79/mo; 3-month recommended minimum to see value.
Cancellation/Refund: Cancel any time; no proration. Special annual plan available at two months free.

Book Now

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