Bouncing Down The Florida Keys

You know it’s true when people say, ” The journey, not the destination is the best reward.” Traveling to a location, especially an island destination, is exponentially more fun than traveling back from one. On the way your body is full of excitement, spirits are high and everything sit in front of you, just waiting for you to take a bite. That’s what it’s like driving to Key West.

This past weekend was the 3rd annual “unofficial” Conched in Key West bar crawl. The purpose of the crawl is to get together with like minded island souls to celebrate life; what better place to do that than Key West!

A group of us decided to take our time getting to Key West and casually bar hop our way through the Florida Keys. This journey, like many others, proved to be half the fun of the entire trip. We hit places like Alabama Jack’s, Caribbean Club, Jimmy Johnson’s Big Chill, Dead Animal Bar, Dockside Tropical Cafe, and finally Tailhook Rum Bar on Key West. A few of those places I had never been before and was excited to check out. So excited that the first three stops took three hours and we had only traveled and grand totally of 10 miles and hadn’t even left Key Largo yet. That’s what happens when you get Castaways together!

Here’s a photo tour of our journey down the Florida Keys. Not mentioned in this story is our drive over the Seven Mile Bridge, I got some great video of our trip over the bridge, but I’m still trying to figure out if what we did was illegal or not. All I can say is EPIC FUN my friends! (Lead photo was taken by Randall D. – part of the Seven Mile fun!)

Bouncing Down The Florida Keys

Alabama Jacks

Alabama Jack’s on Card Sound Road, right before Key Largo. Stop one!


Alabama Jacks

Alabama Jacks

Alabama Jack’s with a great group of people.


Caribbean Club

Caribbean Club, Key Largo


Caribbean Club

Caribbean Club, a great little dive bar on the water.


Caribbean Club

Safari Lounge

Safari Lounge, or what some call the Dead Animal Bar. Islamorada, FL Keys


Safari Lounge

This is why it’s called the Dead Animal Bar.


Tailhook Rum Bar

The Tailhook Rum Bar, Key West


Tailhook Rum Bar

Big Kahuna and Shawn enjoying life at Tailhook Rum Bar. Cheers guys!


Tailhook Rum Bar

Looking back at the photos now, I wish we could do it all over again. Leaving is always so bitter sweet.

I didn’t get any photos at Big Chill or Dockside Tropical Cafe. Jimmy Johnson’s Big Chill is a giant sports bar, which is awesome, but I’m more a fan of interesting little hole-in-the-wall type places when I’m in the Keys. Dockside Tropical Cafe, owned by Eric Stone and Kim Hess will be opening this coming fall. It’s a great place tucked away in a marina on Marathon, you can check out the Dockside Tropical Cafe Facebook page here.

Cheers to taking the road to the end of the line.

About the Author:

Just a salty pirate looking to explore and document the wonders of the Caribbean. Professional blogger, rum judge, consultant, marketer, and consumer of blue water beauty.


  1. Big kahuna October 2, 2013 at 10:00 am

    Wow, did not realize how ready I am to head back!

  2. Becky Bridwell October 2, 2013 at 10:36 am

    getting ready to head to Key West for the first time on the 16th–so excited and glad to see your list of places to check out!

  3. mm
    RumShopRyan October 2, 2013 at 11:35 am

    I’m right there with you Big Kahuna! Didn’t want to leave.

    Becky, you’re going to have a great time. If you need any tips just let me know! Cheers!

  4. Randall October 2, 2013 at 1:03 pm

    Great group of castaways made what was to date my longest one day trip through the keys seem just like a “blink of the eye.” Thanks for chronicling the memories Ryan!!!

  5. Jeff October 2, 2013 at 4:33 pm

    A real deal WAYTOOMUCHFUNCLUB event which included several if not all close friends of mine…..I’ve got to say that I was there in spirit , as I grew up in ‘dem dare Florida Keys and a piece of my soul will always reside throughout Overseas Hwy and especially in Old Town…..the Southernmost City is unique, attractive to all and is truly one place where the square pegs fit into the round holes. Hope to see you merry Castaways down in my neighborhood again soon…til then Peace!~and stay Irie mon’

  6. Carl October 2, 2013 at 4:44 pm

    Great weekend. Great friends. Can’t wait to see you all again soon!

  7. mm
    RumShopRyan October 2, 2013 at 5:29 pm

    Well said Jeff, looking forward to seeing you again my friend. Cheers!

    Thanks for being a part of it and flying in from TX Randall!

  8. Greg October 2, 2013 at 8:22 pm

    So sorry we missed it guys! Thanks for sharing the memories and next time the Coastal gang is in, you can count on it!!

  9. mm
    RumShopRyan October 4, 2013 at 8:12 am

    Already looking forward to it Greg! Cheers!

  10. Tammy October 5, 2013 at 10:48 pm

    Ryan, the time spent with “Like minded” friends is priceless! I am Blessed to have you guys in my circle. As far as the 7-mile bridge escapade – I don’t recall the double stripe ?!?!

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