That sounds like a lifetime adventure. It's a very good time to buy a home if you do your homework, carefully. House costs and maintenance can be what you make it by what you buy and how much you want to do. Property taxes like all other housing costs go up as you look into more preferred areas, especially near or on the coast.

As a sailor, you'll know the better places to keep a boat for the type of sailing you like to do. Your boat can be in an interesting cruising area if you want.

In the end, having owned many houses over the years, we've always made money on them. If it's in a good area, you can rent it easily and cruise part time.