Fun at the Southernmost Point – Key West

If you read our previous post about the Rum Festival you’ll know that we had made our way from Kansas City to Miami. Well the fun didn’t stop there!  After the Rum Festival was over, and we got a good night’s rest, then we headed on down to the keys.  I have to say this is the closest you are going to get to the Caribbean lifestyle and still be able to drive.  Just awesome!

Some people hate the drive because it’s slow and 2 lane most of the way.  But hey, you’re on some islands, what do you expect?  Relax, enjoy the views and make some stops along the way.  Although we do suggest having a designated driver because all those fun little bars along the way can add up to trouble!

Since there were only two of us we took it easy and only made two stops on our way, but next time…well that will be a different story.  Lucky for us the two places we did decide to stop at were awesome.  First up was Island Grill on Islamorada.  Apparently it was voted best Islamorada restaurant, but that wasn’t why we stopped there.  To be honest we didn’t even know that.  It just looked like a place Team Cocktail would dig and it was on the water.  Can’t beat that.  We had a great lunch (highly suggest the fish tacos), a few bloody mary’s and an awesome view.  Put us right in to an island state of mind.


Island Grill on Islamorada


A great view at lunch


Next stop…Looe Key Tiki Bar!  This was the perfect place to stop for a happy hour cocktail.  You can tell the locals love this place as it was packed and everyone seemed to know each other.  Felt like we were in the islands (ok I guess we really were) with the tiki grass roof, palm trees swaying in the wind and a guy playing the guitar. Make this a must stop on your Florida Keys bar tour because we could have stayed here all night.  But since we only had about 24 hours in the Keys we held ourselves back and made the rest of the trip to Key West.

Looe Key Tiki Bar


We rolled in to Key West around 6pm, checked in to our hotel the Lighthouse Court, which was a great little historic inn.  It sat directly across the street from Hemingway’s house and was just a block off Duval street!  Can’t beat that!

We knew we only had one night in Key West so we decided to go all out!  We put on our favorite Team Cocktail shirts, busted out the slap koozies and headed out on the town.  Because we stopped at so many bars I’m going to bullet them in order!

•    Willie T’s – Stopped here because it looked fun and we were really thirsty! Guy playing the guitar, started drinking the local beer (Key West Sunset Ale) and dollar bills all over the bar.  We liked this place so much we have a challenge for you!

1. Go to Willie T’s
2.  Order the local beer – Key West Sunset Ale
3.  Find the dollar bill that says TEAM COCKTAIL
4.  Take a picture with the Sunset Ale & the Team Cocktail dollar bill
5.  Email your photo to
6.  We mail you a FREE Team Cocktail t-shirt!!!  No joke! Follow those steps and you’ll get a FREE Team Cocktail t-shirt!

Team Cocktail Dollar at Willie T’s
It’s a party at Willie T’s

Click here to see see another pic to give you a hint! Now go have some fun and get yourself down to Key West & Willie T’s!

•    Fogarty’s – Stopped here for dinner to fuel up for our big night out.  Great outdoor seating.  Food was good, service was descent.  Can’t say anything bad but wasn’t anything great.  The key was food before the rest of our night!

•    Irish Kevin’s – This is a must visit bar in Key West! I had been here once before about 4 years ago and I must say it is still as lively and awesome as I remembered. Live music, upbeat atmosphere & people just having fun! The live entertainment is great…and they love to make fun of the customers, which is very entertaining.  But watch out if you have a sensitive one in the group…they may want to stay home.

Irish Kevin’s

•    Sloppy Joe’s – Probably one of the most famous bars in Key West.  This place is happenin’ all day long!!  Belly up to the bar or rock out by the stage.  They always have live music & it is a PARTY!!

Sloppy Joe’s
Jim partying it up at Sloppy Joe’s

•    Bourbon Street Pub – So after Sloppy Joe’s kicked us out and we were walking back to our hotel we heard music coming from Bourbon Street Pub so we stopped in for a night cap.  Little did we know this is Key West’s most popular gay bar, or so their website says.  If that’s true we understand why!  The people were awesome, the drinks were great and we had a lot of fun!

After a few drinks & shots at Bourbon Street we finally made our way back home.  What an epic night in Key West…who would have wanted it any other way.  It is the best place for a bar crawl…speaking of which.  Be watching for information about the Conched in Key West Bar Crawl coming up on September 17th!

The next day some of us, and by some I mean one of us, woke up feeling good and ready to take on the day.  The other, well let’s just say he should have taken some Last Round!

But we had to rally because we were meeting Mike from Rum Connection for lunch at Caroline’s. Apparently this is a popular place for the locals which is awesome! We sat at the bar outside, had a great lunch and enjoyed talking with a few locals including Mike! He has an excellent blog about everything that has to do with rum.  And let me tell you…in the Keys rum is king!

Team Cocktail makes the Tip bucket at Carolines – be sure to tip well!
Jim, Lyndsey & Mike from Rum Connection

After lunch we had to do 2 tourist things…visit the Southernmost Point and Mile Marker 0! Definitely worth the great photo ops!

Team Cocktail’s at Mile Marker 0
Team Cocktail at the Southernmost Point

So what did we learn from our trip to Key West?

1.  Staying up all night is the only option.
2.  Go to Willie T’s and hang up your own dollar…there’s just something fun about leaving your mark on a bar.  Oh and good luck finding the TC bill.**
3.  Key West is the perfect place for a bar crawl.  So come crawl with us on September 17th.
4.  24 hours in Key West just isn’t enough time.

One last thought…always remember to TRAVEL GLOBAL, DRINK LOCAL!

Drinking Local…a Key West Sunset Ale

**At time of print only one t-shirt has been awarded in the Willie T. challenge.

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By Lyndsey
We Take Fun Very Seriously!