Continental Command Center

1999 Ocean Alexander 48 Classico - $359,000

Most “Loopers” are content to hug the shoreline, creeping from one protected marina to the next, praying the wind stays below ten knots. They buy boats made of thin fiberglass and dreams. But then there is the traveler who views the Great Loop not as a vacation, but as a deployment.

The Ocean Alexander 48 Classico is for the captain who wants to do the Loop, but also wants the option to hang a right at the tip of Florida and cross the Gulf Stream to the Abacos without spilling a martini. This isn’t a “river boat”; it’s a stabilized, twin-engine fortress. While others are checking the weather app with trembling hands, you’re sitting in a hand-crafted teak salon, stabilized by a Trac system that treats six-foot swells like a minor inconvenience.

This specific 1999 hull is the “Smart Money” find because it bypasses the biggest headache of high-end trawlers: the “Orphan Engine” syndrome. It’s powered by twin Luggers—the legendary, overbuilt diesels that commercial fishermen trust with their lives. Combined with dual Northern Lights generators, this boat is a self-sustaining island. If you want to finish the Loop and then keep going until the water turns turquoise, this is the only hull on our list that won’t ask for permission.