Enjoy the Water AND Get Paid to Boat: 5 Jobs for Captains

boat captain jobs

Boating, yachting, and sailing are a lot of fun. The salubrious benefits of on-water recreation are many. I, probably not unlike many of you, like to go to my boat and just be there… resting, relaxing, or puttering with her systems. And it is always a good time when one invites family and friends aboard for a weekend underway but for some of us, we feel a desire, if not an outright need, to do more with our boating experiences.

There are a variety of ways boat captains can make money doing what they love. On the Chesapeake Bay and its connected waterways, there are several maritime jobs one can seek to spend more time on the water. And these jobs for boat captains can likely be found for waterways near you as well.

Sailing Instructor

Sailing schools are generally plentiful. Nearly every place with a decent marina and ready access to open water has a sailing school. Most are either American Sailing Association or US Sailing affiliated.

If you truly enjoy sailing and have a knack for making sailing sound and look easy to true landlubbers, you may thoroughly enjoy helping new sailors develop their skills. For the affiliated schools, you will need to complete the instructor certifications required by their national entity. While the requirements are generally similar, they may not be exactly the same. Also note that generally speaking an ASA-certified sailing instructor will not be accepted as a staff member at a USS affiliated school and vice versa.

Most classes run on the weekends but some run during the week, especially when students have registered for a comprehensive beginner through bareboat charter sequence.

Towboat Operator

Anyone who has been the water with a VHF radio turned on is well aware of how many calls for assistance go out to TowBoat US and SeaTow. Regardless of whether the situation is caused by bad luck, lack of experience, or bad decisions, there will always be a need for commercial on-water assistance.

At the beginning of the boating season, franchises for the two big tow companies put out a call for tow boat drivers. There may also be smaller independent operators in your area as well. The busiest days are obviously on the weekends. Depending on where you live relative to the tow boat base, you may be able serve on standby at home until a call comes in.

Water Taxis

Some towns have water taxis. On the Chesapeake Bay, towns like Baltimore and Annapolis have multi-boat and multi-route operations. Smaller towns like St. Michaels generally only have a single boat running at any one time with the possible exceptions of busy holiday weekends.

Water taxis tend to want their operators to live locally, probably for on-call reasons. Hourly rates can be low but you may be able to make it worthwhile through gratuities, particularly on holiday or special event weekends. Be advised that the more senior captains will likely get the better schedules and routes.

Additionally some yacht clubs and marinas hire launch operators to take people out to boats on moorings own by the facility. This is very similar to a water taxi but in a much more limited area.

Tour Boat Operator

Excursion operators need captains and sometimes crew for their boats. Think of the DUKW boat fleets in Washington, DC or Philadelphia. There are dinner boat and tour boat operators as well. Some smaller locations may also have opportunities for boat tours for sightseeing or coastal cruises. You may also be called upon to act as a tour guide or otherwise share your local knowledge with the passengers. Many times, private yacht charter fleets need uniformed crew and operators for their vessels.

Yacht Delivery

Lastly, and if you are of a mind to travel, you may wish to consider vessel relocation or yacht delivery. Every year I am at the boat show, I have had Caribbean charter companies ask me about moving yachts between Florida and the Caribbean islands, usually the British Virgin Islands.

Yacht delivery requires a good bit of preparation and experience. Frequently, the opportunities occur on the spur of the moment. It can be a challenging learning event too. Furthermore, you need not necessarily be the lead captain. You could be the relief captain for the off-watch or the mate. Many captains like having licensed personnel along and the owner’s insurance company may require it. I could easily write additional articles about yacht delivery from the perspective of the captain and the owner.

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Boat Captain Qualifications

Some of you may be wondering about qualifications for the jobs listed above. In general there is one requirement that is somewhat inviolate:

You need a Captain’s license

If you are the Master of any vessel and you are being compensated for transporting people or goods, you need to be licensed. If you take a couple of buddies out fishing on your boat and they chip in to cover the expenses, technically you have taken passengers for hire and you may need to be licensed. Most of the crew positions I mentioned above do not require licensing but you may find it easier to get a position as deck crew on a larger yacht, one of the dinner cruises, or some ferries if you are licensed. The sailing school opportunities will all require licenses as well.

If you are a long time boat owner and operator or if you can document time aboard other vessels, if you are up on your navigation skills and, if you know the Rules of the Road fluently, you should not find it too difficult to get a license as an Operator of Uninspected Passenger Vessel or even as a Master.

In my next article in this boat captain series, I will go in to exquisite detail about which license to get and how to get a boat captain’s license. I will also discuss sea time requirements, topics covered on the exams, and things to consider once one has a captain’s license.

Recommended Reading

If you would like a one-on-one consultation to have your specific questions answered on this topic or others related to boating, please sign up for 30 minute video consultation with me!


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Capt. Rob Chichester

View posts by Capt. Rob Chichester
Capt. Rob is an engineer and owner & operator of Chesapeake Flotillas offering charters, instruction, and vessel relocation. A USCG Licensed Master, Capt. Rob has planned and executed flotilla cruises all over the Chesapeake Bay, Europe, and the Caribbean. Rob holds a 200-Ton Master's license with Auxiliary Sail and Assistance Towing endorsements. He also is certified by the American Sailing Association to teach Basic Keelboat Sailing, Basic Coastal Cruising, and Bareboat Chartering. A self-proclaimed sailor & poet, he operates a 41-foot sloop Bay Poet based out of Rock Hall, MD. Rob has also trained and served as captain of tall ships including the state tall ship of New Jersey, the Schooner A.J. Meerwald.


  1. capt rob
    Capt. Rob ChichesterJuly 11, 2018

    Good day and thank you for your question!

    I currently carry a Captain’s liability policy in the amount of $500,000. Such policies are generally secondary policies which pay out after any other coverage that may apply (i.e., boat policy). My current underwriter is Robinson and Sons but I was recently informed that they are not writing any NEW policies. I obtained my coverage through FAM&M in Chestertown, MD. Dan Zotarelli is my agent. His contact information is 1.443.282.3130. and email is DZottarelli@famminc.com. Another option you have is look into getting a general umbrella extension on your home owner’s policy. You can get some significant coverage for not too much of a premium that way. However, in any event, I recommend that you establish an LLC to shield your personal assets from your marine operations. I have done that and my own boat is owned by the LLC. I hope you found this helpful.

  2. Captain TonyJuly 10, 2018

    I have my OUPV and I want to do simple charters on pontoons or boats under 35’ on local lakes and rivers. I want to purchase a minimum level of insurance ($100,000) that would cover me as ILLINOIS does not require boat owners to insure their boats. Can you give me some direction on who to contact? Capt Tony Esposito
    captaintony7272@gmail.com /. 815-322-1177

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