An Outpost Expedition can be scheduled in conjunction with a variety of superb island events and holidays for an unforgettable experience.




Fantasy Fest - Long considered the premier Key West party, this Mardi Gras style bacchanal takes place annually in late October around Halloween. As an Outpost Expedition guests can enjoy spectacular views of the historic Key West Harbor, a variety of watersports, as well as the unrivalled wildlife of the Fantasy Fest Parade. Outrageous costumes strongly recommended.

APBA Off Shore World Championship Powerboat Races - Five days of unbelievable horsepower racing offshore and through Key West Harbor. Guaranteed to get your adrenaline pumping, this is a thrilling world class event. Known to attract sponsors such as Playboy, the eye-candy at these races is certainly not limited to pretty boats and motors.


New Year's Eve - A huge Duval Street party and spectacular fire works over Key West Harbor can cap a fabulous Christmas week get away or start of a new year in a truly memorable style. The fishing is not bad either.


Fishing Tournaments - An array of fabulous fishing tournaments in the islands present an opportunity to pair a yacht charter in a tropical paradise with a competitive thriller.Put your fellow fishing buddies or family up in style for the festivities or enjoy some pre-tournament practice checking out hotspots.



National Family Island Regatta - This spectacular four-day event is held in April. The highly competitive racing of traditional Bahamian sailboats is a stunning sight to behold. Often arriving aboard their family fishing vessels, this regatta is homecoming for many Bahamian families from throughout the islands. Sponsorship by a number of adult beverage companies guarantees the fun.


Cruising Regatta Exuma - Each year in mid-March 400 yachts from all over the world gather in picturesque Elizabeth Harbor in Georgetown, Great Exuma, as if simply watching the spectacle of sailboat racing was an amusing array of other fun filled events such as sand castle building and a talent show held on the beach with a roaring bonfire to delight the participants.


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