Find yourself somewhere else's Travel Blog
Read All's Beach's Family's Outdoors's Skiing Blogemail us

« Top Travel News Stories This Week | Main | Manuel Antonio National Park, Costa Rica »

April 17, 2009

Top Ten Places to Live Like a Pirate

AHOY, MATEYS!: The Flying Dutchman at Disney's Castaway Cay (courtesy, Disney)

The office has been abuzz with pirate talk this week after the somewhat surreal events off the coast of Somalia, no doubt pleasing one of our staffers who is one of the world’s biggest pirate-philes judging from his yearly Halloween pirate fest. But beyond all our swashbuckling pirate wit, it got us thinking about where to travel for some good old-fashioned pirate action—without getting in the crosshairs of AK-47-wielding Somali sea bandits (or indeed sharpshooting Navy SEALs). Here are our top ten picks; tell us if you know any other good pirate hideouts in the comments section below.

#1: Pirate Festivals
Given our colleague's passion for all things pirate, it’s no surprise that there are some fun pirate festivals out there at which to get in the spirit of things. Grand Cayman hosts an annual Pirates Week each November, where revelers dress up as pirates and “invade” the harbor by boat. Tampa’s Gasparilla Pirate Festival, held in early February, is another buccaneering good time.

#2: Blackbeard’s Last Stand
There’s no better ambassador for the pirating fraternity than the 18th century’s Edward Teach, better known to all but his mom as Blackbeard. To get to know the man, mellow out on North Carolina’s Ocracoke Island, a two-and-a-half-hour ferry ride from Cedar Island on the mainland or a shorter 40-minute hop from Hatteras on the Outer Banks. Sample the good life in the Ocracoke Village pub, or hop a kayak for a cruise through the same tidal marshes where Blackbeard met his watery end in 1718.

#3: Disney’s Castaway Cay
Blackbeard might be where the real historical action was at, but it was all Cap’n Jack Sparrow and those pirates of the Caribbean before today’s Somali goons got in on the game. In true schmaltzy Disney fashion, Castaway Cay, a private port-of-call for Disney cruises in the Bahamas, features the pirate ghost ship, The Flying Dutchman, and characters playing the part of Johnny Depp’s now-legendary Captain Jack Sparrow.

#4: Hong Kong & the South China Sea
As a child I lived in Hong Kong and remember seeing news footage of pirates heisting a gleaming S-class Mercedes off to their lair on the back of a high-powered speedboat; the chasing coastguard were no match. Piracy has been a profitable business in this part of the world since as early as 220 A.D. following the tumultuous collapse of the Hang Dynasty. The British put a lid on things to protect their slice of the burgeoning opium trade in the late 19th century, but pirates still see juicy pickings out here in the shape of big shipping lanes that keep the world stocked with cheap plastic toys.

#5: Pirate-Themed Cruises
A little closer to home, but certainly more family-friendly, lots of maritime outfitters put on skull-and-crossbone-themed cruises for l’il (and big) pirates. For example, take a look at the Pirate Adventures cruises that sail out of Annapolis on the Chesapeake Bay or from Manteo in North Carolina’s Outer Banks; there’s also the Captain Memo cruise that sails out of Tampa in search of treasure and some good, clean fun.

#6: Florida Keys
Consistent with its history as a bootlegger and secessionist paradise, the Florida Keys, and in particular Key West, is imbued with a rich history of piracy. All those European navies battling for colonial supremacy brought with them an opposing ragtag posse of gold-digging (literally) opportunists, today’s version of the Afghan warlord. The Keys were the prime strategic hub for raiding opportunities among the islands of the Caribbean, as well as important trading routes linking the New and Old worlds.

#7. Madagascar
This is as close as we’ll get to the Horn of Africa without getting an Uzi aimed at your head. Pirates are the entrepreneurs of the high seas, so it makes perfect sense that they’d sit off the key trading routes for the best pickings. In the early days of the expansion of the British Empire and the flow of goods between the mother country and colonies like India and Malaya, pirates used the Indian Ocean island of Madagascar as their hideout. And unlike today’s Somalia, Madagascar is a peaceful and safe place to visit.

#8. Treasure Island Hotel & Casino, Las Vegas
Where else could you pit a posse of scantily-clad “sirens” and band of testosterone-charged pirates against each other, then devolve it all into what Treasure Island’s website calls a 21st-century party of “music, dance, excitement and seduction”? In the bone-dry desert? Yeah, only in Vegas, where the nightly Sirens of TI performance is probably not quite what those Zodiac-riding Somali teenagers have in mind when they imagine pirate martyrdom. Or not.

#9. Execution Dock, London
It’s not just Hillary Clinton who has a zero-tolerance piracy policy. With supremacy of the oceans of such importance to the expanding British Empire of the 18th and 19th centuries, piracy was one irritant and obstacle for which the punishment was death. Captured pirates were taken to Execution Dock just downstream from the Tower of London on the River Thames, where they’d be taught the ultimate lesson for challenging the rule of the crown. East London’s nearby Captain Kidd pub may be the best place to contemplate if piracy is the career for you.

#10. Tortuga Island, Haiti
There’s a line from my four-year-old son’s CD of Swashbuckling Sea Songs that I can’t get out of my head whenever I read something about piracy these days: “When you see Tortuga’s coast, oh you’re gonna be smilin’; the songs, the fights, the days, the nights, there’s so much to behold.” This small Caribbean isle off the coast of today’s Haiti, so-named by Christopher Columbus because its shape resembled a turtle, was one of the first hideouts for Spanish-hating French boucaniers after the Spanish drove them off the island of Hispaniola (now Haiti and the Dominican Republic). The island still has that primitive, forgotten feel—though you can probably leave your cutlass at home.

Email this post   |   Permalink

Related Topics: Beach Vacation · Caribbean Travel · Disney Vacation · Family Vacation · Florida Vacation · Top 10 Lists


Feed You can follow this conversation by subscribing to the comment feed for this post.

A great post! One question, can you live a pirate life with three toddlers under four hanging off your arms? If you can fit all of them on the plane without having passengers bludgeon you than I suppose these could work! I will let you know on our next visit to Costa Rica.

"Execution Dock" is located on the Thames in the Wapping area of London, England, United Kingdom. It was used for more than 400 years (as late as 1830) to hang pirates, smugglers and mutineers that had been sentenced to death by Admiralty courts.

I just like this top ten list. These are the finest places for family vacation in the world. All these places are very beautiful. Thanks for amazing post. Its an very helpful information for all of us.

Love the list, great places for adventure and pretend to be a pirate. I am sure I would not want to meet a real on on the seas.


I enjoyed your article.

For me, I am living each and every day as a Pirate. For me, the pirate life is a life of freedom. Being able to do what I want to do when I want to do it! Freedom...

So the pirate lifestyle is more of a state of mind than a physical location. Sure, it is fun to go to interesting places. But I prefer to live each day like a pirate!


Captain Rob

I love this top ten list. This is such a great site for families looking to plan a vacation or just those looking for a little adventure. South Carolina coast has a great pirate history as well and a great place to visit is Dataw Island in Beaufort, South Carolina while you embark on South Carolina's adventures.

Thanks for the comment, Somali_Pirate, but we figured that Somalia might need a few years to mature as an adventure-travel destination before our readers are ready to send in their trip deposits.

Hi Alistair, this is a really great top ten list. My parents are from Hong Kong and I remember them telling me about pirates when I was younger which helped fuel my interest in them. You can post this to our site and then link back to your site. We are looking for top ten lists and our users can track back to your site. The coolest feature is you can let other people vote on the rankings of your list. We have quite a few pirate lists that have become very popular recently, and I'm sure our readers would really enjoy your list too.

Where Is Somalia On The List?

Too Bad They Didn't Make It.

what a fun article. i dont know if i'd so much want to live as a pirate as i would want to visit. and they majority of these place you have listed are great visiting towns with tons to do for everyone!!!
The Travel Expert(a) and an Expat with a Twist

The comments to this entry are closed.


Subscribe to Our RSS Feeds

  • RSS Feed of All Travel Posts
      AddThis Feed Button
  • RSS Feed of Family Travel Posts
      AddThis Feed Button
  • RSS Feed of Beach Travel Posts
      AddThis Feed Button
  • RSS Feed of Outdoor Adventure Travel Posts
      AddThis Feed Button

Most Recent Posts

Recent Comments

Our Topics

Away's Blogroll


Technorati Profile