Traveling to Key West - What the Guide Books Don't Tell You

Writer’s Block: It’s A Bitch

That’s why I’ve been back from Key West for 4 months now and I still can’t write about it. It seems I found a piece of myself on that island, a piece that’s made it hard for me to put pen to paper. I’m finally able to share some of the more memorable moments of our trip and some insights on traveling to Key West that you won’t find in guide books.

Ann & I were in Florida for TBEX and decided to knock an item off our bucket list while we were there. Driving down hwy 1, crossing the 7 mile bridge, was like falling down a rabbit hole and finding a mysterious and wonderful secret world. Time… doesn’t exist on the island.  Except the scheduled departure for your sunset cruise. But don’t worry, even if you’re late by one minute you now have the excuse to eat at some fabulous restaurants.  Many have ‘happy hour’ specials when drinks and apps are ½ price.  Can you say… Yum?

Travel tip: If you love steak as much as I do and you either don’t like the high price tag or the huge portions order a steak salad or a flank steak appetizer. It’s served BESIDE the salad, not on it, and the portion is perfect.

Add a side of steam veggies or mashed potatoes and you’re eating like a king without mortgaging your kids.

When planning your trip to the keys remember – Location, Location, location.  ‘Waterfront’ or  ‘Ocean front’ is not synonymous with ‘close to the action’.

The island is bigger than it appears and if you’re not careful you’ll end up in the most gorgeous hotel by the ocean a quarter mile from Duval street…. Which is a surprising 15 minute cab ride downtown for this Canadian girl who screwed up the conversion.

The first thing you’ll want to do as you step out of the car is turn your face to the sun… soak up some therapeutic rays, breath in the smell of the salt in the air, and listen to the waves crashing against the shore.

That’s the sound of the island trying to seduce you.

Once you’re done feeling sorry for yourself ‘cause you can’t have this year round you should head to Duval St and Mallory Square where you can shop, dine, and stroll to your heart’s content.

Mallory square is a great place to find unique items, official Conch Republic souvenirs, and gorgeous jewelry.  On Duval st you’ll be able to find fashions of all kind… for all kinds of bodies.

Travel Tip: If you have any body issues whatsoever I strongly suggest you head south.  It seems the further south you go the smaller the clothes gets.

Our trip coincided with Fantasy Fest think… Mardi Gras on crack – and I can assure you bodies of all kinds were seen.  Never mind shilling out beads for a flash – Body paint is the fabric of choice during these festivities.  I’ve never seen so many Nekkid people at once before.

At the table next to us at the restaurant was a woman wearing nothing but a grass skirt and artful body paint.  Men were wearing what can only be described as leather nutsacks on a string and group theme costumes were all the rage.

Beyond the obvious though I saw a few things that can’t be unseen.  I’m remembering one fella with red glitter paint on his crotch and a peter pan color at his neck.  A very, very, old couple bared all except for the world’s largest spray painted bush and some body paint that had seen better days.

General rule of thumb?  Don’t look down, even if it’s high tide / full moon and you want to make sure the wet thing you just stepped in was water and not other bodily fluids mixed with booze.

Looking down means you have to look back up and that can only lead to blindness and night terrors.  Seriously – you couldn’t look up without coming face to face with a full frontal. I can assure you, the George clooney’s of the island clearly stayed home. 

We also experienced Zombie night.  I never in a million years imagined the words ‘If there weren’t so many zombies around I wouldn’t feel as safe’ would escape my mouth.

I also never imagined myself being greeted by 10 thousand zombies and 2 police officers 400 metres from the airport entrance.  Needless to say I called budget and told them the zombie apocalypse was right outside their door and we would be late returning our rental car.

My favorite activity during our trip? The Sebago Power Adventure Tour.

We were brought out to the coral reef to snorkel – and me with my glasses – and no contacts – I chose to dive in blind for fear of my glasses ending up in the ocean.  I have no idea what the reef looks like, I couldn’t see jack-sqwat.

I was hell bent on parasailing though so I maguyvered some holders to make sure I got the best view from the top.  Soon everyone was making holders with yellow duct tape.  The captain said it best – it takes a Canadian to come up with the best ideas. 


I’m afraid of heights but when that parachute lets go and the rope unravels all you feel is freedom.  It’s like floating through the air on a cloud.  I was so comfortable I would have stayed up there all day if I could. That piece of me I found was up there above the water and I could only bring back the memory of it.

I’ve decided that I now must go parasailing in every coastal city I visit, if only to revisit that part of my soul that refuses to touch ground.

None of the locals are locals, and as Ms Beth (one of our Sebago captains and all around awesome woman) would say people just fall in love and come back because they can’t imagine living anywhere else.  I can believe it!

They weren’t kidding when they said it was the best sunset in the world.

Every night crowds gather at the pier for the sunset celebration. Mermaids playing the yukelele, sword swallowers telling tall tales and fresh-made-right-in-front of you guacamole are just a few of the highlights well after the sun bids farewell.

Key West is truly a magical place and I can’t wait to go back!  I hope you’ve enjoyed the video (missed it?  At top of page 😉) and the pictures.

Now that you’ve learned a few new things about traveling to Key West that the guide books won’t tell you go ahead and start planning your dream adventure.  You deserve it!

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