Why You Should Book a Trip to Key West


Hey there! Are you up for a weekend getaway? Us, too! We have our eyes set on the south, and we mean the most southern point of the continental United States, Key West. 

What’s not to love about this historic and eccentric island that straddles the point between the Caribbean Sea and the Gulf of Mexico? 

You have gorgeous, calm waters all around, a relaxed, colorful island vibe, and events, shopping, and attractions around every corner that will keep you entertained and wide-eyed. Oh, did we mention the world renowned dive sites? And the chickens? (Yes, chickens… all over. Running wild. We love them).

Brief History of Key West

For a 4.2 square mile island, this tiny patch of land we now know as Key West is packed with history. From being a forgotten graveyard, to passing in possession from country to country, to becoming the richest city per capita in the U.S., and a brief rebellious attempted secession, this is a small town with some serious main character backstory.

Once upon a time, the Calusa and Tequesta native inhabitants of the Keys used the island as a communal graveyard. Due to the amount of bones that were found there, the Spanish conquerors who claimed the island originally called it Cayo Hueso, meaning “Bone Cay”. 

Due to its prime location, it became an island of much interest and over the years passed in possession from Spain to Great Britain to the United States (officially de facto property of the U.S. on March 25, 1822).   

Fast-forward about a century and a half through major hurricanes and an incredibly lucrative time for business on the island, and we find ourselves in 1982. During this time the U.S Border Patrol created a blockade on US1, the only way to drive to and from Key West, in order to search every car for potential migrants. The traffic was so backed up that tourists stopped visiting, causing an extreme loss in revenue for the island. Thus, the Conch (pronounced konk) Republic was born, announcing independence from the United States. Although a faux secession, the Conch Republic created enough attention to the island’s protests that the Border Patrol ended the blockade. Conch Republic is very much a part of the Florida Keys culture to this day with their Independence Day celebration every year on April 23.      

This 4-miles-long and 1-mile-wide island is now home to 26,444 inhabitants (according to the 2020 census) and has the welcoming motto of “One Human Family”.

How to Get to Key West

As we mentioned in the previous section, you can take the road trip route through South Florida and make your way down US1 all the way to Mile Marker 0. In the process, you’ll see the absolute beauty of the waters and wildlife and many still undisturbed islands. You’ll also cross over the Seven Miles Bridge which is the ninth longest bridge in the United States. 

Your other option is hopping on a flight. The Key West Airport (EYW) is a small airport with only six gates and an alarmingly small landing strip. So be prepared for an abrupt stop when flying into this location. 

If you’re coming from the West Coast of Florida or just want a unique way to get to Key West, you could even take a boat from either Fort Myers Beach or Marco Island via the Key West Express.


There are plenty of hotel options around the island from quaint and charming boutique hotels to elegant resort-style stays. Additionally, the range of home rentals is just as vast, from extraordinary waterfront wonders to renting space on folks’ liveaboard boats. So, when looking for a place to call home for a bit, you’ll find just what you need from the wide variety of stays on this little, spectacular island.

Best Times of Year to Visit Key West

While Key West is amazing to visit any time of the year, there are some factors that may sway when you stay. Temperatures, rainfall, hurricane season, hotel prices, and crowds are much of what can shift when we want to visit. 

The winters are cool to warm with clear, sunny skies nearly every day. Such a tropical paradise in the winter months brings tourists in droves and, thus, higher hotel prices. So if you’re looking for an international party with some impeccable weather, winter is where it’s at.

Want to avoid the crowds and vacation on a budget? The summers are amazing for catching great hotel deals and feeling like you have a little more breathing room while you wander down Duval Street. The summer months though tend to come with unpredictable weather—the only sure prediction being heat and humidity. 

The autumn months bring even more unpredictable weather and amazing room rates since hurricane season is at its peak. But if the weather happens to act right while you’re there, there can be some incredible opportunities for diving and crowd-free island enjoyment. 

If you had to make us choose, though, the spring is possibly the best time of year for a visit. Many of the winter visitors have left as the temperatures climb again, causing loads of availability and good rates on rooms and some truly delightful weather. 

Where to Go and What to Do

You’ve made it here! You’ve checked in to your desired place to stay. What now? 

Well, while Key West is the perfect place to simply live spontaneously and go with the flow, a tentative itinerary can help you be sure you don’t miss out on all that the island has to offer. 

Some absolute Must-Do activities include walking and shopping down the famous Duval Street, watching a sunset at Mallory Square, and, of course, getting in the water, whether snorkeling, scuba diving, freediving, paddle boarding, boating, and more. 

Some extras, should you choose to make it a more educational visit, include visiting the Ernest Hemingway House, the Harry S. Truman Little White House, and the Tennessee Williams House.

Another historic attraction that’s a little more on the adventurous side is the Dry Tortugas National Park. Hop on a ferry that’ll take you even further west to an island that is the home of Fort Jefferson. The coral reefs, marine life, and incredible bird life around the park make this a nature experience you can enjoy from land or, if you bring your snorkel or scuba gear, you can get in the water and explore the thriving reefs. 

Be sure to stop by Divers Direct in Key West to pick up your scuba, snorkeling, or beach gear for the day! 

As you may have guessed from the original state of this island when found by the Spanish, it is also a great place to explore the supernatural. Therefore, hop on a ghost tour trolley and get to know the spooky side of things here.

There are more restaurants and bars on this little island than we can list here, but just know you can’t really make a bad decision on where to eat or party. But a couple of staple joints that don’t disappoint include the Conch Republic Seafood Company, Sloppy Joe’s Bar, and the Banana Café. 

Remember to grab an iconic photo with the landmark Southernmost Point Buoy and with the Cuban Coffee Queen Key West postcard mural. 

Visit the Smathers Beach or Higgs Memorial Beach to watch a sunrise you’ll be sure to remember.

Best Key West Dive/Snorkel Spots

It’s no secret (or surprise) that one of the most famous dives in Key West is the USNS Vandenberg artificial reef. It is the second largest artificial reef in the world and is a unique wreck dive you’ll be glad you went on. The highest point of this massive military transport and missile tracking ship sits at around 40-feet, while its sandy resting ground is 140-feet deep. This is a unique structure that’s abundant with sea life such as goliath grouper, moray eels, parrotfish, and more. If you’re a diver visiting Key West, this is a must-dive experience. 

Another popular dive around Key West is the Cayman Salvage Master, which lies about 7 miles southeast of the island. While originally intended to be sunk at 300-feet, a few cables snapped in transport to its intended location and the Cayman Salvager sank to a 90-foot sandy bottom. Goliath grouper, moray eels, and many gamefish call the wreck their home. Due to the often strong and unpredictable currents, this dive is only for advanced and technical divers.

Not too far from the Cayman Salvager lies Joe’s Tug, which isn’t really a tug boat at all. It’s a steel hulled shrimp boat with quite the mysterious and mischievous backstory. When the shrimper sank at a harbor in the 1980s, it was refloated and intended for transportation to Miami as an artificial reef. But the night before its move date, it sank seven miles off the coast of Key West. Many believe pirates commandeered the boat but simply didn’t make it far. Sitting in just 65-feet of water, beginner and advanced divers can enjoy its thriving marine life and frequently good visibility. 

Finally, the Western Sambo Reef Reserve is about five miles off the coast of Key West, just south of Boca Chica Key, and is a large tract of coral formations that is just brimming with marine life. As a part of the Florida Keys National Marine Sanctuary, hunting is prohibited in this nine-square nautical mile area, making for a safe space for fish to simply be. The variety of depth and bottom structure provide a multi-faceted experience.

Why Key West is One of the Best

Small but mighty, this little island is jam packed with things to do and ways to have fun and enjoy life. Whether you’re slightly above sea level enjoying its land-based attractions or if you’re exploring the world below the surface, Key West is an adventure you’ll remember for a lifetime. That is why it’s one of the best places to visit. 

Grab your scuba gear or snorkel stuff (or pick some up at Divers Direct) and get to booking your tropical stay at this world-renowned vacation destination. 


Is it expensive to travel to Key West? 

While Key West currently has some startlingly high real estate, visiting this island is surprisingly affordable. Finding the right travel plan and accommodations has never been easier and the cuisine and experiences are worth every penny. 

When is the best time of year to visit Key West? 

Key West is so gorgeous year round that the only not-so-great time to visit is the late summer to early fall due to hurricane season—though you will find great deals for stays during those months. The more populated (and expensive) times to visit are the winter months, and the summers are perfect for a warm, tropical getaway. 

What is Key West known for? 

Key West is known for a great many things: Beautiful, clear waters, an eccentric, yet laid back island personality, wild chickens, great scuba diving and water sports, fantastic food, and a culturally diverse atmosphere. 

Why is Key West known as the Conch Republic? 

U.S. Border Patrol once created a blockade along US1 (the only road in and out of the Keys) to check every car for migrants. This caused such a traffic nightmare that tourism came to an abrupt halt. Key West felt as though they were being treated like a foreign country, so, in response, decided to secede from the U.S. and be known as the Conch Republic. The secession never went through, but the event caused such a stir that the Border Patrol ended the blockade. The Conch Republic flags still fly around Key West and it has been their nickname ever since.