The Osprey 1 is fittingly named; it was Osprey Cruises' first and only boat back in 1971, when the company first started. Back then, the 70-foot vessel's main routes were for carrying fishermen and spectators up to 100 miles out into the Gulf of Mexico for fishing trips and wildlife watching. And it does so today, too—it's just ceded some of its star status to the fleet's newer vessels.

And they're a compelling bunch. Take the aptly named The Thriller, a high-speed offshore racer for adrenaline cruises. Or, perhaps even more enticing, The Black Dragon. It's a recreation of a 17th-century Spanish galleon helmed by a crew of costumed pirates, rather than their less-reliable parrots. On pirate cruises, these swashbucklers share pirate stories, send passengers on treasure hunts, and generally introduce them to the grog-and-swordfighting lifestyle. Many trips happen upon schools of dolphins along the way or offer evening jaunts amid captivating sunset views.