Minnesota_husker

I'm with @Toe - not to discourage what you want to do, but I'm not really a fan of cruises. It feels quite constricting overall, and when you do get to leave the cruise and visit land, it can feel a bit like sheepherding. And, personally, I don't really think you get the flavor of the places you visit during the short time frame you get to be on the land.

That said, if you want to do a cruise, check out cruises that head down the western coast of North America to places like Puerto Vallarta. I think that's an underrated place to visit because people usually think of Cabo and Cancun, but it's a beautiful city with wonderful people, and when you visit the downtown area, it doesn't really feel like you're in a tourist destination.

Thanks for all the opinions people... The wifey and I are discussing options. 

I do prefer all-inclusive resorts in Mex/Carib over cruises, but cruises are fun too.  The huge boats ships they are building now are basically floating resorts, with multiple restaurants and a great variety of entertainment.  Yes, there is a "sheep herding" aspect to them, but you get to wake up in a different place every morning, which is kinda cool.  One problem the nickel and diming on board, and even if you are moderate drinker, you will ring up quite to bill at the end of the trip.

But when I go on "tropical" vacations, I prefer to plant my a$$ down by a pool/ocean and drink all day, so all inclusives are more my style. Mrs Red Five is more of the "get out and do things" type, so she likes being able to see different things on a cruise.