Three Ways to Tour Key West

Key West is a small island, about 2 miles by 4 miles, but there are a lot of attractions and a lot of history packed into those eight square miles.  Obviously, you can walk or drive around the island on your own to see the sights, but there are also several ways to jump start your visit and really get to know the Conch Republic.  We already talked about the Old Town Trolley tour in our Exploring Key West post.  Here are three more fun ways to explore this treasure of an island:

Conch Train

The Conch Train has been around since 1958 and has shown Key West to millions of visitors.  We boarded the train at its depot on Front Street then sat back to enjoy the ride.   The tour winds through the main streets and the back streets of Key West giving you close up looks of the key points of interest.  Our driver (JC) told us a lot of stories as we drove around; giving us lots of information on the people, history and architecture of this little city.  There are three stops on this train and if you want you can hop off, look around, and catch the next train; however, we just sat back and rode the whole way.

The Key West Conch Train. All aboard!

The Key West Conch Train. All aboard!

The train cars are open, but covered, and you get a very up-close and personal feel on this ride making it seem like we could reach out and touch those chickens! (And iguanas, too!) It seemed like everyone in Key West was in a good mood during our ride as virtually everyone waved at us as we passed by!

I suggest taking this tour early in your visit so you have a better understanding and appreciation of Key West. Here’s a link to their website: Key West Conch Train.

Ghosts & Gravestones

If you’re wanting to know more about Key West’s darker side then you might want to take the Ghosts and Graveyards Tour.  This tour begins on Front Street where you board The Trolley of the Doomed…and yes, we had second thoughts before getting on!   On board we were greeted by Lulu who was dressed in a period costume and she immediately told us we were doomed.  Hmm….we were starting to get a little apprehensive what with all this “doomed” stuff.  Lulu then gave us instructions on how to react when passer-bys yelled “You’re Doomed” at us.  Huh…what’s she talking about?

We're doomed!!!

We’re doomed!!!

We then began driving the streets of Key West while Lulu told us stories of murder, mayhem and hauntings. For such a small city there certainly were a lot of stories!  Things got a little personal when the trolley stopped in front of our hotel (The Banyan Resort) to tell us about sightings of a ghostly sea captain.  Wow, this was the first we had heard that!  (Note: Unlike our stay at The Farley House in Savanah (Savannah) we did not have any encounters with anything spooky at The Banyan.  Darn!)

And on this tour,  just like the Conch Train Tour, there is a lot of interaction with pedestrians.  As you drive along you’ll hear someone shout “You’re Doomed” and everyone on the bus would yell back in unison, “Yes, we are the doomed!”  Amazing how many times this happened!

The highlight of the tour was our stop at the Fort East Martello: a Civil War fort that is known for being haunted.  Here we were led through the dark fort grounds by another guide in a period costume.  Then we went inside the fort which is now a museum and which has this creepy doll, Robert, on display.  Robert the Doll has a very creepy backstory involving voodoo and stories about Robert moving around on his own.  (Could Robert be the inspiration for Chucky?)

Robert the sure to ask permission!

Robert the Doll….be sure to ask permission!

Robert is in a glass display case and it’s said that he still moves in the case from time to time.  As I said, Robert is pretty creepy and you have to ask his permission before you take his photo otherwise something might happen to you.  And yes, we most certainly asked Robert for permission to take his picture.  So far so good!

You may not get scared on this tour (unless Robert moves), but you’ll definitely laugh!  For more information you can go to: Ghosts and Gravestones.

Key West Cocktail Challenge

Key West is well known for its bars and restaurants which are primarily concentrated on the western end of the island.  A great way to get to know this area is to simply walk around and what better way to do that than by trekking from bar to bar and trying their speciality drinks.  Not only will you meet some pretty interesting people on your trek, you’ll also get a cool tee shirt when you complete the challenge.  (Lucky for us, you don’t have to visit all six bars in one night.  You can stretch out the challenge over your entire visit, as we did.)

You can do the challenge in any order you like, but for us we started at the marina at the Half Shell Raw Bar.  Their signature drink is The Oyster Shooter and it comes in a glass that you get to keep.  Oysters, jalapeño vodka and a free shot glass…can it get any better?

Jalapeno vodka, oysters, and cocktail sauce. Yum!

Jalapeno vodka, oysters, and cocktail sauce. Yum!

Over the next few days we continued with the challenge: Turtle Kraals, The Rum Barrel, Island Dogs and Charlie Macs where they also serve some awesome BBQ!  At each place we met  fellow challengees and exchanged war stories on each other’s progress.

A friendly Key West chicken comes to visit us at Charlie Macs!

A friendly Key West chicken comes to visit us at Charlie Macs!

We finished our challenge at the legendary Green Parrot Bar, a Key West icon which traces its roots back to the 1890s.  Here we settled in to enjoy their signature drink, The Root Beer Barrel, while listening to a great band.  There is a great blend of locals and tourists here and it’s a great way to spend an evening.  On top of that, we got our tee shirts here!

Inside the iconic Green Parrot. If you go remember, NO SNIVELLING!

Inside the iconic Green Parrot. If you go remember, NO SNIVELLING!

We recommend you sign up for the challenge early in your trip so you have plenty of time to complete your trek.  Remember to walk safe!

No matter how you learn your way around Key West I’m sure you will enjoy your visit.  We’ve visited the island twice and are ready to go back!

More Key West information:

Here’s a great resource to learn more about what you can do and see in Key West: Florida Keys.



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