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2011 Pirates in Paradise Festival

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Ahoy all!

The preliminary schedule for the Pirates in Paradise Festival at the Truman Annex Waterfront is up at

It includes several new events:

1st annual Boucan Cookoff

1st annual Home Brew Fest

1st annual Sea Chantey Championship

Interactive Movie Night

1st Annual Jolly Roger ‘Hard Aground’ Land-ship Sailing Race

2011 marks the return of the Tall Tales Championship, two performances of the Tryal of Anne and Mary, guest lectures, Coloring with Don Maitz, the Pirate Pub and the El Meson de Pepe Pirate Feast.

Several events have changed dates to make room for the new events and End of Hurricane Season, which falls on Wednesday.

The Bad Ass Pirate & Buxom Wench Costume Contest is on Tuesday this year.

The 7th Annual National Walk the Plank Championships are now on Saturday.

An all-hands Pirate's Ball is tentatively scheduled for Saturday night.

I'm sure new stuff will be added as the year moves along but wanted to get this up for those planning to attend Pirates in Paradise this year.

That is all.

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Big things coming to PiP. . . . The festival will rock with fresh new ideas and crowd draws from the general public, cruise ships, etc. . . . it's gonna' ROCK and we're glad to be on board!!!

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Was on the phone with the rest of the planners. Lots of great things on the horizon after getting our feet wet in the new location. Can't wait to share some of the plans once they are firmed up. Right now, I have to finish the marketing plan for the darned thing.

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1st annual Boucan Cookoff

Niiice. I look forward to that addition.

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How about that idea we talked about last weekend?

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I have shared it with the committee Commodore and it's on the list.

There's just a few other things on the more immediate plans to handle (grants and such).

Looks like we may be adding a weeklong music festival at night. The Bad Ass Pirate and Buxom Wench will be on-site this year as part of a Pirate's Ball. I personally am looking forward to movie night. We'll be showing Crimson Pirate on the wall of the building there and Reap the Wild Wind before it. I hope to do Crimson in a Rocky Horror format.

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I hope to do Crimson in a Rocky Horror format.

Perhaps you could hold the Walk the Plank contest in conjunction with the Time Warp.

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The festival schedule has been completely updated. For those of you who come to town early or want to attend all the other events, some of the key events have been shifted to accommodate the 11 day festival.

The El Meson Caribbean Pirate's Buffett will be Tuesday, Nov. 29. The Buxom Wench and Bad Ass Pirate contest will be Wednesday, following the End of Hurricane season flag burning. It will be held at the Pirate Pub at the Truman Waterfront, not Schooner Bar (this is new). The Shoot & Sail has been moved to Thursday for everyone who wants to compete on open water with life rounds and period weapons. A good chance to check your accuracy aboard a heaving deck.

The Walk the Plank Championship will be on Saturday again, Dec. 3 with the Tall Tales Competition directly after.

New to the Sea Chantey Festival this year will be Best Original Song. We're looking for chantymen and musicians who will pen and original song for the festival. This should capture the essence of the Pirates in Paradise Maritime Heritage Festival & Music Festival. Draw your inspiration from any and all events. We will be having the competition for best song at 11 a.m. Sunday, Dec. 4. Email me for more information -

For the complete schedule:

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Some additions to the festival plans:

For those wishing to come down early, there will be the opportunity to do vending at the Pirates in Paradise Truman Annex location from Thanksgiving until the day the fort festival opens. Set up would be 11/23 and tear down would be Thursday 12/1. The fee is $225 if commercial items, $50 less is hand crafted.

With the addition of the carnival this year and live concerts each night (working on Bo Bice and The Wailers among others), the traffic should be fairly good this year.

There is another new contest: Picture Pirates in Paradise... rules to follow on that one, but the winner's photos will be featured on the home page (and perhaps other pages of the Pirates in Paradise, be used for media photos worldwide and perhaps be on one of the posters for 2012 (depends on reproduction requirements of the image), complete with your PHOTO BY ____________ Winner for the 2011 Picture Pirates in Paradise Contest.

We're also thinking of adding a festival songwriting contest for best theme song that captures Pirates in Paradise. Still working on that one.

More coming... so much coming this year it's hard to keep track of it all.

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An update on events at the Truman Annex and around town:


Featuring Swashbuckling Special Events & Piratical Escapades for all ages!


Pirate Tours of Key West’s Pub Strolls & History Tours (11/24-12/4)

Robert N. Macomber’s Key West Reader Rendezvous (11/28-12/1)

Historic Glimpses Talk - The History of Grog featuring Robert Macomber (11/28)

Walking Tour of Old Town with Robert Macomber (11/29)

El Meson de Pepe’s Caribbean Pirates Dinner (11/29)

Kelly’s Caribbean Authors, Artists & Historians Luncheon (11/30)


Pirate Sails & Attacks (11/24-12/4)

Conch Republic Shoot & Sail (12/1)

Authors, Artists & Historians Sail (12/1)


Admission: $5/adults, free for kids 12 and under (11/24 thru 12/4)*

Living History Encampments

Period Arts & Crafts

Holiday Bazaar

Vintage Vittles & Grog

Fight Circles

Swashbuckling Swordplay

Games of Chance

Carnival Rides

Kid‘s Play Area

Pirate Art 101 with Don Maitz

Knot Tying Demos

Period Weapons Demonstrations

Pirate Pub

Swashbuckling Pyrate Cinema Under the Stars (11/24 & 12/1)

Official End of America’s 2011 Hurricane Season Party (11/30)

Most Buxom Wench & Bad Ass Pirate Costume Contest (11/30)

Pyrate Tryal of Anne Bonny & Mary Read (12/2 & 3)

Pyrates of the Coast National Walk the Plank Championships Aboard WOLF (12/3)

International Pirate’s Hall of Fame Tall Tales Storytelling Competition (12/3)

Jolly Roger “Hard Aground” Land Ship Regatta (12/4)

Historical Presentations: The Young Wreckers, Matt Lowe and more...

*Additional gate fees may apply after 3 p.m. during special events and Concerts Under the Stars


Thankstakin’ Pirate Feast (11/24)

Concerts Under the Stars on the Waterfront

Conch Navy Craft Beer Tasting & ASTAAR’s Equine Foundation’s Beer for Our Horses Fundraiser (11/26 &


Sailor’s Shipwreck Holiday Ball, Pirate Feast & Swing Dance (11/27)

Cayo Hueso Boucan BBQ & Chili Cook-off (12/3)

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