Just decide first on the coverages you may need. Is the boat going to stay in Milwaukee all year round, or will it be travelling South in the winter, perhaps to Florida and the Bahamas during Hurricane season. Figure out what you are going to be doing and at what times of the year so you can let an insurance agent know your needs. A traditional Marine Insurer should be able to provide, in an as needed basis, additional Endorsements for coverage for specific travel trips. For example, you want to sail the Bahamas for a month then you can purchase a specific coverage for that trip. Find a good marine insurance agent in your area, tell him how you intend to use your boat and allow him to advise you regarding what coverages and companies would best fit your needs and what would be the best rates for the coverages.