Book Now!

The Conch Connection

A First Timers Guide to Key West

Updated on: Jul 18, 2022 4:44:53 PM

So, you're thinking of a vacation to Florida's Southernmost Island, but you're not sure what to expect! The most striking thing about the island that you'll first encounter is that the populace is a little bit of everyone. Famous celebrities to the average Joe. Island natives who've never left the island to world travelers. And every walk of life in-between.  Sit back, relax and's island time.

Geography 101

To start with, lets get the geography lesson out of the way. Key West sits near the end of a string of islands "keys" that are best known as The Florida Keys and Key West. They start directly below the mainland and the everglades, just south of Miami and stretch in an almost  westerly string to Key West, which is the last major "key" or island. The absolute "last" key is Dry Tortugas, which is about another 70 miles further west. Key West is actually closer to Cuba than mainland Florida.

Things to do in Key West

The predominantly pedestrian island is relatively small, measuring approximately 2 x 4 miles with a permanent population slightly under 30,000. 

People Watching

There is no greater social equalizer that exists than clothing! Here in Key West, the fashions of the day are a comfy pair of shorts, swimsuit, a t-shirt and flip-flops. That person walking beside you or sitting next to you on a bar stool could very well be a multi-millionaire or someone rubbing his last two dimes together.  Think Ernest Hemingway sitting on his bar stool enjoying his favorite libation at Sloppy Joe's. . .

People from all walks of life seem to migrate and congregate here. So, don't be afraid to strike up a conversation with the person next to you. You might just discover a friend for life or discover that little tid-bit of life changing dialog. Credit: Piqsels

The island's motto is "One Human Family". It was a local grass-roots movement that eventually spread over the island and came to be accepted by all. The basic premise being "All people are equal members of One Human Family - regardless of race, nationality, sexuality, and other differences".

Out on the Town

One of the first things that you'll notice here are the CHICKENS! Yes, chickens run freely throughout the island. First brought to the island for their obvious nutritional value, the island is now a wildlife refuge where they're protected by law.

The main drag through town is Duval Street. This stretches about 1.5 miles from the Gulf of Mexico to the Atlantic Ocean. Here you'll find every bar and restaurant imaginable that makes it a mecca for people watching.  Exploring on and around Duval Street is the perfect atmosphere to enjoy the "touristy" side of the island.

To really discover the heart and soul of the island, we suggest you hit the side streets to discover some of the island hidden gems. Whether by foot or bike, you'll be free to explore and wander at your own pace through the wonderfully unique island neighborhoods.  

Lions and Tigers and Bears, Oh My!

Ok, not really.  But, during your meandering you'll come across many of the islands art galleries, museums and other attractions. The galleries here are simply world class where you'll find gems that will inspire and swell the emotions. Credit: Piqsels

Since Key West is and has been the stopping off point or the pause in the road for many, there are museums that can educate your mind, body and soul. Ernest Hemingway, John Audubon, Tennessee Williams, Jimmy Buffett and many others have made Key West a stopping point in their lives.

The Wrap UP

Given Key West's eclectic, wild and wacky, free thinking "anything" goes atmosphere and tropical temperate climate, there isn't too much more to say (ok, we lied about that part, just read some of our other blog articles!!).  It's time to dive into all that there is to see and do!  Come aboard the Key West Express to head south to the Island of Pirates, Presidents, Poets & Partygoers.

Book Now

If you're looking for some other great things to do in Key West, be sure to check out our Key West Adventures Page.

Hero Image Photo Credit: Piqsels

Topics: Insider, Old-Town, Information

Have something to say? Comment below!!

Subscribe Here!

Recent Posts