June 19 – Swashbuckler

Let Your Freak Flag Fly

Pirates are pretty legendary customers. Just by listening to “A Pirate’s Life for Me,” we get an idea of what it was like during their time, even if it is Disney-fied. Sometimes a flag was all that was needed to terrorize anything from a ship to a settlement. Here are some of the most famous pirate flags from the golden age of swashbucklers:


This is a pretty epic portrayal of a skeleton pirate king, complete with goblet (other sources say that it’s an hourglass, but I’d like to think it’s a rum goblet). Perhaps this could be an early depiction of cupid, as he is trying to put a spear through a heart. Apparently this signified that no mercy would be given to any captive. Blackbeard was some badass. Legend has it that he would put smoking fuses into his hair and beard to make himself look demonic and strike fear into those he wished to attack.


Black Bart 1

Bart’s first flag showed that time was running out for his victims with the pirate and skeleton both hanging onto an hourglass (again, I like to believe it’s a goblet fit for all the booze a pirate can handle). Bart captured approximately 400 ships in his three-year career as a pirate, which is a long tenure during those times.

Black Bart 1

Black Bart 2

This one has Bart standing on top of the heads of captains from his two least favourite ports, Barbados and Martinique. The ABH stood for “A Barbadian’s Head”, while AMH was “A Martinico’s Head”. Bart treated seized ships and their captains and crew from these ports especially bad because their colonial governments were always after him.

Black Bart 2

Calico Jack

This is the pirate flag that most of us recognize, thanks to its popularity in modern media. Ironically, Jack wasn’t a very successful pirate captain, but he is remembered for allowing women to join his ship (although the harlots totally betrayed him) and, of course, for this flag. The skull over crossed cutlasses has largely been recognized as the most common flag and now represents all pirates to some degree.

Calico Jack

Henry Morgan

I had to include our good friend, Captain Morgan, whose rums have always been stocked at the Sip Advisor headquarters. Morgan used the classic “skull and crossbones” flag, but with the added twist of the skull wearing an eye patch. Why he did this, isn’t entirely clear. It’s not like he wore a similar patch and the skull was meant to depict himself. Morgan was so successful that he was able to retire from piracy and became Lieutenant Governor of Jamaica.

Henry Morgan

Drink #170: Swashbuckler

Swashbuckler Cocktail

  • 1.25 oz Tequila (I used 1800 Reposado)
  • 0.75 oz Grand Marnier
  • 2 oz Sweet & Sour Mix
  • Top with Fruit Punch
  • Garnish with Red and Green Grapes and Runts

If I had ever been granted the luxury of being a pirate, my flag would have depicted a bottle of rum being poured into the open mouth of a smiling skull as the skeleton was giving a thumbs up gesture. Damn, I would have been one rockin’ buccaneer!

Sip Advisor Bar Notes (4 Sips out of 5):
I’ve been wanting to play with Fruit Punch for some time now and I’m glad I finally had the opportunity. It’s a hell of a mixer, tasting so good and refreshing… perhaps my favourite of all the fruit juices. I’m a little surprised with a drink called Swashbuckler, that Tequila was the featured alcohol, over Rum, but whatevs.

2 thoughts on “June 19 – Swashbuckler

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