Back in the 1980s, big beautiful schooners were still among the most desirable offerings of Caribbean charter fleets, and a number of high-profile celebrities were often seen in popular anchorages of St. Barth, Bequia and elsewhere, aboard their splendid old-timey boats: Bob Dylan’s schooner Waterpearl and Neil Young’s Baltic Trader Ragland, were among the most famous back then. But these days, the times they are a changin’.   

While state-of-the-art megayachts — both power and sail — now dominate the Caribbean’s luxury charter scene, many celebrities have swapped traditional yachts for high-tech vessels built for speed, comfort and easy access to that clear, turquoise water. A standout within this trend is crooner Jimmy Buffett’s sexy new Surfari 44, designed by Ted Fountaine of Friendship Yacht Company, and currently being built by Pacific Seacraft in North Carolina with a November launch target. 

Among its slick innovations is its fold-down transom "tailgate" that doubles as a swim step; a sun-protected helm station in the deck-level salon with 360-degree visibility due to large forward and side windows, and sliding glass cockpit doors; and "push-button" controls for running rigging, all of which is led to the cockpit.

As you might image, Jimmy’s Surfari 44 (whose name has not yet been released), employs composite construction with a carbon mast and boom. She’ll carry both a roller-furling genoa and a furling asymmetrical spinnaker on a sprit, both of which are controllable from the salon. When winds go light, her twin 75-hp auxiliaries will ensure that Jimmy doesn’t miss the party.

A lifelong waterman, Jimmy Buffett has owned many power-  and sailboats — including the beautiful Cheoy Lee Clipper Euphoria II, aboard which he penned Cheeseburger in Paradise and other Caribbean classics. It’s anybody’s guess what sort of tunes Jimmy’s sleek new ride will inspire.