Frequently Asked Questions
The questions we get most often — about delivery, coaching, pricing, and how this all works.
The fastest way to figure out whether we're a fit for your situation is to ask. This page collects the questions we hear most often on intro calls, organized by topic. If your question isn't here, pick up the phone — the conversation is free and we like talking about boats.
Vessel Delivery
Do you handle deliveries outside the Great Lakes?
Yes. Most of our work is on the Great Lakes — Lake Erie, Lake St. Clair, the Detroit River, and Lake Huron — but we deliver throughout the continental U.S. East Coast deliveries, Great Loop legs, and snowbird relocations from the Great Lakes to Florida are routes we run regularly. The home base is southeast Michigan; the operating range is wherever the boat needs to go.
What size boats do you deliver?
Vessels from 30 to 65 feet. The USCG credentials authorize larger, but most of our actual work is in that size range — the boats most recreational owners are buying, moving, or repositioning.
How far in advance do I need to book a delivery?
For peak season runs — May through September on the Great Lakes — typically 4 to 6 weeks of lead time. Shoulder season (April, October) is often easier to schedule. Snowbird runs to Florida book up early — September dates for southbound runs and April dates for northbound runs are typically claimed by July. The earlier the conversation starts, the more dates we have available.
Can you deliver in winter?
It depends on the route. The Great Lakes themselves are closed to most recreational delivery by mid-November and don't reopen until April. Florida and Gulf routes run year-round. If you're trying to reposition a boat in the off-season, we'll talk through what's feasible and what isn't.
What happens if there's a mechanical failure during the delivery?
The captain isn't a marine mechanic — that's stated explicitly in the delivery contract. If something goes wrong mechanically during the trip, the captain manages the situation, coordinates with marinas or mechanics as needed, and the daily rate continues to apply while the boat is being repaired. You're not paying for the captain to fix the boat; you're paying for the captain to manage the situation responsibly.
What if the weather gets bad?
The captain has the final call on whether the boat goes, holds, or alters course. That authority is built into the contract for exactly this reason — no boat owner wants their captain pushing into conditions that put the vessel at risk because of schedule pressure. Layover days due to weather are part of the structure and are billed at the layover rate per the contract.
Do I have to be aboard during the delivery?
No. Most deliveries are run with the captain solo or with a single crewmember the captain provides. The owner meets the boat at the destination. If you want to ride along and learn the boat at the same time, that's a different service — owner-assisted delivery.
Can I send my family or friends along on the delivery?
That's a conversation. Some routes and some vessels can accommodate additional passengers comfortably; others can't. The bigger consideration is liability — the insurance rider needs to cover everyone aboard, and the captain's authority over operational decisions doesn't change because there are passengers. If it makes sense for your situation, we'll work it out in the contract.
Coaching
What's the difference between Captain's Coaching and First Mate Coaching?
Captain's Coaching teaches you to run your boat. Five modules — docking, running the boat, anchoring, trip planning, and creating a log. Aimed at the person at the helm. First Mate Coaching teaches the other person on the boat — the spouse, the family member, the friend — how to handle the line and fender work, the radio, the dock-hand coordination, and what to do in an emergency if the captain goes down. The two programs complement each other, and most pairs benefit from both.
Who is Captain's Coaching for?
New boat owners, owners moving up to a larger vessel, and experienced boaters who want to sharpen specific skills. The five-module program is structured but flexible — we work in your home waters, on your boat, at a pace that matches your starting point. You don't need any specific level of prior experience.
Who is First Mate Coaching for?
The other person on the boat. Often a spouse who wants to be more than a passenger. Sometimes an adult child being trained to handle the boat alongside the captain. Sometimes a friend who's joining the crew for a long trip. The First Mate program is the only one of its kind on the Great Lakes that we're aware of — most coaching programs focus on the captain, and the first mate is left to learn through observation.
How long does the Captain's Coaching program take?
Depends on how it's structured. Some owners run all five modules in three or four intensive days. Others spread them across a season, one module per week or month, so each lesson has time to be practiced between sessions. We design the schedule around how you actually want to learn.
Do you have to do all five modules?
No. The modules are designed to work standalone or in sequence. If you're confident with docking but want focused work on anchoring, we run just the anchoring module. If you want the full program, we run all five.
Can I do coaching on my boat or only on yours?
Always on your boat. The whole point is to learn your specific vessel — how she handles, where her quirks are, what she does in your home waters. Coaching on a different boat would defeat the purpose.
What if my boat isn't at the home dock yet — do I still need coaching?
This is when owner-assisted delivery makes more sense than standalone coaching. We deliver the boat home with you aboard, learning her on the trip. By the time she's at the dock, you've already done a multi-day intensive on your own vessel. It combines both services into one engagement.
What's covered in the First Mate emergency protocol?
If the captain becomes incapacitated for any reason — medical emergency, injury, anything — the first mate needs to be able to operate the radio, relay position, drop anchor to prevent grounding, run the boat to a safe location, or return the vessel to a dock. The First Mate Coaching program covers each of these directly. The First Mate's Emergency Playbook walks through the full protocol in detail.
Owner-Assisted Delivery
What is owner-assisted delivery?
It's a delivery model where you hire the captain to run your boat home — but you ride along, at the helm, learning the boat through hands-on operation under the captain's coaching during the trip. Every docking is a teaching docking. Every anchoring is a teaching anchoring. By the time the boat reaches the home dock, you've learned more about your vessel than most owners learn in their first two seasons.
How is owner-assisted delivery different from straight delivery?
Straight delivery is a transport service — the captain runs the boat, you meet it at the destination. Owner-assisted delivery is a transport service with coaching built in — you're aboard, at the helm, learning the boat through the trip. Same delivery work, additional value.
How is it different from Captain's Coaching?
Captain's Coaching is run in your home waters, on a boat that's already at your home dock. Owner-assisted delivery is run during the trip to the home dock — the boat is on the move, you're learning it on real water in real conditions. Owner-assisted is the right answer when both delivery and coaching are needed; standalone coaching is the right answer when the boat is already where it belongs.
Is the cost different from a straight delivery?
The structure is the same — daily rate, travel expenses, deposit. The coaching is the value-add; the rate doesn't change because we're teaching during the run.
Can my spouse or first mate come along and learn too?
Yes, and most do. First mate coaching runs in parallel during the trip at no separate structural charge. By the end, two people on the boat know how she works, not just one.
Do I have to be at the helm the entire trip?
No. You're at the helm for the parts you want to learn — usually that's the dockings, close-quarters work, channel transits, and a meaningful stretch of open-water running each day. When you want a break, the captain takes it.
What if I realize partway through that I don't want to be at the helm?
Then the captain takes the boat home. Owner-assisted is built around what you want to learn. If at some point you'd rather just ride, we run it as a straight delivery from there. No renegotiation.
Pricing & Process
How much does a delivery cost?
Pricing is structured around a daily rate plus travel expenses plus a deposit, but the actual quote depends on the vessel, the route, the season, and how many days the run will realistically take. We don't publish a rate sheet because every delivery is different enough that a single number would mislead more than it would help. The conversation about your specific trip is free — that's where you get an honest number.
Why don't you publish your prices on the website?
Because every delivery is unique enough that a single advertised rate wouldn't be accurate. A four-day Lake Erie delivery has different cost factors than a fourteen-day Great Lakes-to-Florida run on the same boat. We'd rather have a fifteen-minute conversation and give you a real number than publish a price that requires asterisks and footnotes to actually apply.
How does coaching pricing work?
Coaching is structured similarly — there's a per-module rate for the Captain's Coaching program and a separate rate for First Mate Coaching, but the actual cost depends on which modules you want, how the schedule is built, and where your home waters are. Same approach as delivery: the conversation is the path to a real number.
What's the deposit, and is it refundable?
A non-refundable deposit is required to secure the dates for any delivery or extended coaching engagement. The amount depends on the trip — typically a percentage of the estimated total. The deposit is credited against the final invoice when the work is completed.
What happens to the deposit if I cancel?
Per the standard delivery contract, cancellations made with at least 20 days of written notice before the planned start date forfeit only the deposit. Cancellations with fewer than 20 days of notice may incur additional expenses already incurred (airfare, travel costs, etc.) plus retention of the deposit. If the voyage has already started and the owner terminates, the daily rate applies through the termination date plus return travel costs.
Do you take credit cards?
We handle payment through standard business channels — typically check or bank transfer for the deposit and final settlement. Credit card payment can be arranged in some cases but involves processing fees that ultimately get passed through.
What's the typical engagement timeline?
For a delivery: initial call → quote and contract within a few days → signed contract and deposit → insurance rider confirmation → delivery on the planned dates → final settlement. Most owners go from first call to signed contract within a week. For coaching: similar timeline, often slightly faster since there's no deposit-and-rider coordination involved.
Insurance & Logistics
Do I need an insurance rider to hire a delivery captain?
Yes. The standard delivery contract requires the owner to secure a rider on their existing marine insurance policy naming the captain as an approved operator for the dates of the delivery. The process is straightforward — typically a single phone call to your carrier, 24 to 48 hours of turnaround, and confirmation back to the captain. The full why-and-how is here.
What does my carrier need to issue the rider?
The captain's USCG Mariner Reference Number (2913289), the captain's credential information, the delivery dates, and the vessel information. Most carriers can issue the rider with that alone. If your carrier needs the captain's credentials submitted on a specific document, we have a standard submission document we can provide.
Does the rider add to my insurance premium?
Most carriers issue the rider at no additional premium for the duration of the delivery. A few may add a small surcharge. Your carrier will tell you when you call.
What if my carrier won't issue a rider?
Rare but possible. If a carrier refuses to issue a rider naming a USCG-licensed Master Captain with active credentials, the issue is usually with the carrier's underwriting practices rather than with the captain's qualifications. We can have a conversation with the carrier directly if needed, or you may need to consider whether your existing insurance is adequate for the kind of operation you're planning.
What about coaching — does that need insurance coordination?
For most coaching engagements, no separate rider is required because the boat owner is operating the vessel under the captain's instruction. Your existing policy covers you as operator. We'll confirm this with your specific situation during the contract conversation.
Do you carry your own insurance?
Yes. Offshore Captain Services LLC carries professional liability coverage appropriate to the work. The owner's hull and machinery coverage is the policy that addresses damage to the vessel itself, which is why the rider exists — it's the mechanism that makes your existing policy apply during the trip.
What happens if there's an incident during the delivery?
The captain handles the situation according to standard maritime practice — documents the incident, notifies the owner and the relevant authorities, coordinates with insurance carriers, and works toward resolution. Having the rider in place beforehand is what makes the insurance process straightforward when something does happen.
What documentation do I need to provide before the delivery?
Standard items: current vessel registration, proof of insurance with rider, the signed delivery agreement, and access to the boat (keys, alarm codes, dock access if applicable). The full pre-delivery checklist is in the addendum to the standard delivery contract.
About Captain Tom
What are Captain Tom's credentials?
Captain Tom holds a USCG Merchant Mariner Credential with two active Master licenses: 100 Gross Register Tons for the Great Lakes and Inland Waters, and 50 Gross Register Tons for Near Coastal Waters. Both licenses carry the Commercial Towing Assistance Endorsement. The credentials were originally issued in 2009 and have been maintained continuously since. The USCG Mariner Reference Number is 2913289.
How long has Captain Tom been doing this?
Captain Tom has spent thirty-six years in the automotive, commercial truck, and marine supply industries, and a lifetime on the water. He's a former Commodore of the Ford Yacht Club, served three years on the FYC Board of Directors (2004–2006), and currently serves as President of the Ford Yacht Club Past Commodores. Offshore Captain Services LLC was founded after his retirement from industry to focus on captain services full-time.
Is Offshore Captain Services a one-person operation?
For most work, yes — Captain Tom personally captains the deliveries and runs the coaching engagements. On extended runs that require additional crew, Captain Tom brings in qualified credentialed mariners he's worked with previously. The work is owner-operated; you're hiring the captain whose name is on the credentials.
Why do you only work in this size range?
Vessels from 30 to 65 feet are the size where USCG-credentialed coaching and delivery have the most value for the typical recreational owner — large enough that operational complexity matters, small enough that the captain-owner relationship stays direct. Larger commercial vessels are a different specialty. Smaller boats often don't justify the cost.
What's the difference between hiring you and hiring a delivery captain off a national directory?
The honest answer: not always much, if the other captain has comparable credentials and the right insurance setup. Where the difference shows up is in three places — the working knowledge of southeast Michigan and Great Lakes waters specifically, the coaching component (which most delivery captains don't offer), and the size of the operation (small enough that you're working directly with the captain, not with a dispatcher). Whether those differences matter for your situation is a question worth asking on a call.
How do I know if you're the right captain for my trip?
Talk to us. Twenty minutes on the phone tells both of us pretty quickly whether the fit is right. We're not the right captain for every owner or every trip — sometimes the right answer is a different captain, sometimes the right answer is moving the boat yourself, sometimes the right answer is trucking it. Honest conversation gets to the right answer faster than a sales pitch.
Can I read reviews of your work?
Endorsements from past clients and colleagues are posted on the About page and on our Google Business Profile. We also have a collection of endorsements if you want to see more.