Hiring a captain to deliver your sailboat is a little different than hiring one for a powerboat. Sure, many captains do deliveries on both power and sailboats. But even then, not all have the same qualifications.
Let’s look at what makes a sailboat delivery different and how that may affect which captain you hire for your delivery.

Speed
It seems obvious, a sailboat is slower than a powerboat. But how does that affect your delivery?
Your captain will have to be better able to accurately judge how many miles per day your boat can travel. And many factors play into that—weather, engine size, onshore or offshore passages, number of crew aboard, sail inventory aboard, and more.
Miscalculating may lead to more days for the delivery than quoted (thus more money than initially quoted). It could also mean more or different overnight stops—having to stay at a marina instead of the planned anchorage (also more money).
There is also a safety factor. You’ll want a captain that genuinely understands the speed and power of your sailboat. For example, if they navigate an inlet, will they have calculated the time well enough to arrive in daylight? Have they checked the tides? While going against an outgoing tide in a narrow inlet may be nothing for a powerboat, it can slow an underpowered sailboat to a knot.
Draft
If your sailboat has a deeper draft, there may be well-traveled routes that are not an option. Even shoaled in channels can be a concern. A delivery captain used to working on sailboats will be more aware of areas that may need to be avoided our only navigated when timed with the tide, reducing the chance of running aground in your boat.
Bridge Clearances
While any captain should be able to look up the bridge clearances within the delivery route, a sailboat delivery captain will be more familiar with how the bridge restrictions will affect the overall time delivery timeframe. In South Florida, for example, some sailboats will have a difficult time making it from one timed bridge opening to another, reducing the distance considerably for the day. The captain may also have to circle in tight and congested areas with a strong current in front of the bridge while waiting for an opening. A sailboat captain will have more experience in safely handling the boat.
Weather
Indeed, weather plays a part in any boat delivery, but more so for sailboat deliveries. A powerboat will be less affected by the direction of the wind. But on a sailboat, the wind direction is critical—even if motoring. Delivery captains with more sailing experience will make better judgment calls on how the weather will affect the boat and make changes to the route, adjust sailing angles for comfort, or even select different anchorages for the night.
Sailing Knowledge
It’s when things don’t go as planned that hiring an experienced sailboat delivery captain really makes a difference. Will your captain know how to handle the boat under sail if the engine cuts out? Will they be able to react instinctively if the halyard wraps and prevents the sail from furling? How quickly will your captain be able to troubleshoot a steering problem? All captains should be skilled at man-overboard procedures, but will yours know by nature how to handle a rescue under full sail in any sea condition?
Specialized Equipment
While power and sailboats share a lot of the same equipment—navigation, VHF radios, and safety gear. There is usually a lot of specialized gear on a sailboat that your delivery captain will have to become quickly familiar with. Even the charging systems may be different. The charging systems may be more dependent on solar or wind and have smaller battery bank sizes. Access to the engine and other systems may be more difficult.

What licenses should my captain have?
Your delivery captain should—at a minimum—have a current USCG license.
Note: USCG Captain’s Licenses must be renewed every five years. You can verify your captain’s license with the Department of Homeland Security.
There are two primary types of licenses your delivery captain is likely to have. Let’s break them down to understand the differences:
- OUPV-This is commonly referred to as the “six-pack” license. It allows the captain to operate a non-inspected vessel (a recreational vessel) up to 100 tons (roughly 100 feet). In addition, they are allowed to have up to 6 people on board (this includes paid crew and guests combined).
- 25/50/100 Ton Master License-These licenses allow the captain to operate non-inspected and inspected vessels (commercial vessels—like ferries and water taxis). The size vessel is dependent on the license, from 25 tons to 100 tons. Captains that hold this license may carry more than 6 people on board.
- USCG Sailing Endorsement-Captains that carry the Master License can also obtain either an inland or near coastal USCG Sailing Endorsement. (Note: Captains with the OUPV license cannot add a sailing endorsement to their license).
Since most sailboat delivery captains will have the OUPV license and will not be eligible for the USCG Sailing endorsement to demonstrate their hours of experience or testing competency.
So, as a boat owner, how do you determine your captain’s sailing experience?
Ask specific questions, follow up on referrals, and read their previous client’s testimonials. If you are new to sailing, it may be helpful to have a knowledgeable friend with boats like yours to be present while talking to prospective captains. Or you can work with a reputable captain and crew placement company, and they will handle all they will be able to match the most suitable captain for you, your boat, and delivery location.
Preferably you’ll want to hire a delivery captain that has experience with similar boats to yours. However, even sailboats can vary dramatically in handling depending on their build. For example, a heavy, full-displacement monohull and a light, the high-freeboard catamaran will handle almost every condition differently. They will have different points of sail that are most comfortable for the boat (and crew), react to large seas differently, and use different approaches when docking.
Of course, it doesn’t mean that your delivery captain isn’t fully capable of adapting to a new boat, but given a choice between two equally competent and personally compatible sailboat delivery captains, it makes sense to choose the one who won’t be learning aboard your boat.
Do I need more than just a captain for the delivery?
Maybe. There are a lot of factors that determine how many crew should be aboard—the size of the boat, the length of the delivery, the route, and more. Many companies that provide delivery services will require a minimum of a captain and mate aboard any sailboat.
Note: If you are hiring a private captain for your sailboat delivery and they will be selecting their own crew, make sure they aren’t just bringing their girlfriend/boyfriend who has little experience along for the vacation. If you are paying for extra crew, you want them to be fully capable of handling your boat in place of the captain if needed.
How many hired boat delivery crew members you have onboard may also depend on if you will be aboard your sailboat for the delivery and your experience level.
What should I ask a prospective sailboat delivery captain?
In addition to all the other questions you should ask when hiring a delivery service, here are a few specifically for sailboat delivery captains:
- What licenses do you have? Do you have a sailing endorsement?
- Tell me about other deliveries you have made.
- How much time have you spent on boats like mine?
- Do you know of any depth or bridge restrictions along the proposed route?
- Do you see any challenges with my boat specifically handling this trip?
There are a lot of exceptionally skilled and capable delivery captains available. You just need to know how to sift through the less experienced captains to find the best one for you.
Do you have any tips on hiring a delivery captain on sailboats? Please share with us in the comments.