St Augustine Pirate Pub Crawl

St. Augustine Walking Tours has done the impossible!  They’ve made this lover of history and hater of beer enjoy two things I never thought I’d like.  Pirates and Beer.

When you sign up for your tour, you’ll receive a welcome email that shares when & where to meet… the pirate changes up the tour so look alive, matey!  Pirate Anne Bonny took us to some new-to-me, local pubs and I learned to understand {if not like…} Pirates and Privateers.

I love that our tour was more than a dressed-up-guide walking us from bar to bar.  No, Anne Bonny is serious about her period clothing {Ahem. It’s not a costume.}, she’s serious about her weapons {the gun fires and the knives are sharp}, and she’s serious about her history.

We all know pirates are generally the bad guys.  St Augustine historians may prefer you to focus on the fort, free Africans who settled here and Indians.  But St. Augustine does have it’s share of pirate history- for example, did you know we wouldn’t have the Castillo de San Marcos if it weren’t for pirates?!  True story!

Protip: If you want to look really smart on the tour, go to the St. Augustine Pirate Museum first.  😉

This pix is a nod to St. Augustine Walking Tours’ logo.  Yes, I actually wore tennis shoes with a dress.  I totally rocked the tourist look.  {embarrassing!}  Seriously, though, don’t wear heels to a walking tour, ladies.  You will be walking across town, so make it pleasant!

We popped into Old Town Wine Cellar and I was surprised by the destination, it’s size and comfort {great chairs!}.  I’m sure I had walked by 1,000 times before but never even peeked inside!  I tried their White Sangria and found it refreshing.  {Sidenote: my favorite Red Sangria so far is Rhett’s.}  Our Pirate shared fascinating stories at each stop but also allowed time for chit chat- great balance of facts & fun.

When we turned down Hypolita and then onto Spanish Street, I knew exactly where we were headed.  Barley Republic Irish Public House!  This pirate knows the best off-the-beaten-path spots!  {See Red in the kilt?  He’s the owner- he stocks some good stuff!}

I tried the Dirty Hoe.  I know, it sounds terrible.  I think that’s the point.  But the Lambic covers the taste of the Hoeegaarden and makes for a sweet-tart bubbly drink.  Okay, I guess that doesn’t officially make me a *beer* lover but I did find something that was tasty!

We stopped in two other pubs- I won’t tell all her secrets though.  You should go and experience it for yourself!  At only $15 per person (book online for that special rate), it was a super-fun way to spend an evening.  You get 1 free beer at the first place and then order what you’d like the rest of the evening.  This was great for me- I’m a lightweight and only had a drink at 2 stops, so I appreciated only paying for what I actually drank.

At the end of the evening, Anne Bonny sang us some sea shanties, steered us to favorite places to eat and shared some parting pirate wisdom.  Over the course of our 3 hours together, I tried new drinks, visited new pubs and made new friends.  For Anne, it’s all in a day’s work.  For me, it was a mem-arrrrrgh-able evening.  {Horrid, I know, but I couldn’t resist!!}

St. Augustine Historic Walking Tours Pirate Pub Crawl
If you’re travelling with the kiddies, they also offer a Historic Pirate Tour for families!  Check out their site for other options, including St. Augustine tasting tours.


We were welcomed on a tour so we could share our experience with you.  All opinions are my very own.  Pinky promise.

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