A unique opportunity to sail the Caribbean islands you’ve been hearing Jimmy Buffett sing and write about for years- Jost Van Dyke, Anguilla, Tortola, and more. Hangout at barefoot beach bars such as Foxy’s, the Soggy Dollar, and Sunshine’s. Feast on a cheeseburger in paradise as you mix with the locals at the famous Le Select bar in St. Barts.

All while enjoying live performances throughout the week from our own Barefoot Islands Cruise Band featuring Scott Nickerson, founding member of the first official Jimmy Buffet tribute band A1A, and Founder of Parrot Heads in Paradise. This exclusive full ship charter of the 312 passenger motor-sailing ship Wind Surf of Windstar Cruise Lines will have us island hopping the best of the Caribbean
in luxury. The intimate size of this beautiful five-masted ship will allow us to visit the smaller, out-of-the-way islands not accessible to large cruise ships. We will be anchored off islands with our launches landing passengers at small docks or directly onto beaches. Our custom itinerary will allow us to stay at these anchorages most evenings so we can fully experience the legendary local nightlife and establishments. Clear blue waters, white sand beaches, and bountiful boat drinks-The ultimate attitude adjustment!
“We could not have been more pleased with the entire trip and pre-process of the trip. Location, Hotel, Service, People, Music, Food, everything was perfect. …Again, thank you for all that you did to make THE BEST VACATION I have ever had in my 43 young years. Hat’s off!”
Kelly
Big Head Todd and the Monsters- Hawaii 2007
Produced by Local Knowledge
Jimmy Buffett is not associated with, nor will be participating in, The Barefoot Islands Cruise. The terms Jimmy Buffett and Parrot Head(s) are registered trademarks of Margaritaville, Inc. Parrot Heads in Paradise is a registered trademark of Parrot Heads in Paradise, Inc. Windstar Cruises- Ship’s Registry: Bahamian.

