A question for you captains out there...

There are / have been many discussions on the topic already.
If you use the search tool of the forum, (up top) you'll be sure to come across them and have a good few hours worth of reading should you choose.

In a nutshell...The first license you can get is the OUPV, more commonly known as the 6-pack. Before you can take the exam you need to be able to document 360 days of experience at sea. Pass a physical examination, pass a drug test and enroll in a random testing program. Acquire a TWIC card, and finally pass the coast guard exam. Most people go through a maritime school such as Sea-School to help them through the process. They will prepare you for the exam and help you assemble all of your documentation to be submitted to the USCG. The biggest hurdle for most people is gaining the required experience and being able to document it. Good luck, I hope this helps.

That may be misinterpreted.... It is the USCG license with the least amount of sea time available, but it is not the "first license you can get" in that you can qualify for higher grade licenses with no prior license as long as one has the requisite experience.

One can also qualify for insurance under the MCA/RYA system with a Yachtmaster certificate without the seatime qualifications (though there are some qualifications,30 days, 2 days as skipper, 800 miles, 12 night hours (if you hold the Yachtmaster Coastal course certificate this is reduced to 20 days, 2 days as skipper, 400 miles, 12 night hours) for Coastal or 50 days, 2,500 miles including at least 5 passages over 60 miles measured along the rhumb line from the port of departure to the destination, acting as skipper for at least two of these passages and including two which have involved overnight passages. 5 days experience as skipper. At least half this mileage and passages must be in tidal waters. All qualifying seatime must be within 10 years prior to the exam. For Offshore, more info here: http://www.rya.org.uk/coursestraining/exams/Pages/Coastalskipper.aspx
) or TWIC card (A biometric ID card issues by the US TSA) and other such nonsense that a private operator doesn't need. The RYA system was inaugurated just for such reason, to qualify the owner operator as competent for insurance. It does not matter as to your nationality, and there are several schools in the US such as IYT that are qualified through the RYA to issue a Yachtmaster cert.

Insurance may very well cover you anyway with no license if you have a reasonable prior history with boats. I've also been called to train and sign off owner operators for insurance companies. Another thing to consider though that if one plans to retire on an 80+' boat is maintaining it. It's daily work, a good bit of it strenuous work. It may end up being a better deal to hire a captain/engineer with experience and ability who can do the things you may otherwise neglect until you have to call in an outside contractor. Boats degrade very quickly, and in an expensive fashion if they are not maintained on a daily basis.

BTW, there is no such thing as a "Captain's License" it's a Master's License.

That won't work for him in Maryland, U.S.A. The lowest license is actually launch operator, but that would also not apply here. You're insurance company is also very likely to look at related experience, not just holding a license. So, a quick 6 pack license probably won't get your boat insured. And quite frankly, if you don't have the experience to more than qualify for a 100GT license, you really should have an experienced captain aboard. To do otherwise would be penny wise and pound foolish. 80' is a pretty serious vessel. You don't need to hire someone full-time if your willing to work and have the time, but he should be behind you ready to take over when cruising.