Smathers Beach, Key West, FL

A Photo Essay: Key West, FL

Somehow, Key West continues to draw me in with a tighter grasp every time I set foot on its sizzling shores. I have visited this tiny island paradise more times than I can count (and yes, I can count into double digits, thank you very much), and each time I discover numerous new activities that I never knew existed, and my ever-growing “to do list” keeps getting longer by the mile. The laid back island is so much more than Duval Street, “90 miles to Cuba” and Cheeseburgers in Paradise. There is a different and slightly adventurous side to the island believe it or not, and the vast amount of history is sure to turn heads on any pirate loving individuals. This past July was surprisingly my first time visiting Key West since starting this site, so it was fun to hop around and view the island with fresh eyes again, and with that, here is our photo essay of Key West, FL, and I’m sure it won’t be the last!

Sloppy Joe's Bar, Key West, FL

Ernest Hemingway used to frequent Sloppy Joe’s bar when it was located down the street. Now, the bar holds an annual Hemingway look-alike contest.

Custom House, Key West, FL

The multitude of statues surrounding the Custom House Museum are always fun to strike a pose with.

Old Town Trolley Tours, Key West, FL

Old Town Trolley Tours and Conch Trains line the streets to give visitors a look into the past and current day Key West.

Antique Shop, Key West, FL

This antique shop near the Historic Seaport area felt more like a treasure trove with all it’s unique historic findings.

Key West, FL

Air conditioning is a welcome treat when basking in the glowing sun all day long.

Key West, FL

Knickknacks line the streets on the plentiful stands found throughout town.

Key West Conch Fritters, Key West, FL

Conch fritters are a popular treat that can be found throughout the island on most any menu.

Pirate Ship, Key West, FL

Pirates are an integral part of Key West’s history and you are sure to find numerous sightings of the town’s shady and exciting past when wandering.

Sunset Sail, Key West, FL

Getting out on the water is a great idea when visiting Key West. To date, our favorite vessel has been on a sailboat.

Sunset Sail, Key West, FL

Sailing is hard work, but it still looks like fun–we watched the crew climb up into the sails.

Sunset Sail, Key West, FL

Nautical rope adorns the side of the boat and looks quite nice against the setting sun.

Sunset Sail, Key West, FL

Watching this plane fly overhead while riding along a schooner sailboat made us feel like we stepped back into time.

Parasailing, Key West, FL

Parasails soar through the air as riders take in the beautiful, spanning views of the island.

Parasailing, Key West, FL

The views really are great from up in the clouds, and it’s so much more peaceful than I would have ever thought.

Jetpack, Key West, FL

Watching the jetpack adventures entertained us–maybe we can try it one of these days!

Beach at Fort Zachary Taylor State Historic Site, Key West, FL

Fort Zachary Taylor State Historic Site is located off the beaten path in Key West. If you didn’t know it was there, you wouldn’t happen upon it.

Beach at Fort Zachary Taylor State Historic Site, Key West, FL

At the park, you can find beautiful trees and great views of the ocean.

Beach at Fort Zachary Taylor State Historic Site, Key West, FL

There are also plenty of picnic tables and a generous amount of shade in case you need a break from the sun.

Beach at Fort Zachary Taylor State Historic Site, Key West, FL

The water at Fort Zachary was so clear–it makes a great spot for snorkeling if you don’t mind a rocky beach.

Key West, FL

How far are you from Key West?

Sunset Key, Key West, FL

Directly off the shore from Mallory Square, rests Sunset Key. If you want to visit, make sure to get out your checkbook–it’s a pretty penny. For a more affordable way to visit, book a reservation at the island’s restaurant.

Smathers Beach, Key West, FL

Even though Smathers Beach is man-made, it sure is paradise!

Historic Seaport, Key West, FL

Wander around the Historic Seaport of Key West to find shops, restaurants and boats galore.

Streets of Key West, FL

Despite the rundown look, the streets of Key West have an abundance of character.

Southernmost Point, Key West, FL

The infamous “Southernmost Point” of the United States–when standing here you are closer to Cuba than Miami.

Mile Marker 0, Key West, FL

Mile Marker 0 marks the end of US Route 1. This road runs all the way from Canada to Key West.

Key West, FL

This beautiful tree never escapes being photographed by us when we visit–it’s just so enchanting!

Cannons at Fort Zachary Taylor State Historic Site, Key West, FL

When visiting the beach at Fort Zachary Taylor, be sure to make a pit stop for a history lesson at the Fort. You will learn a bit about how the military protected the island many years ago.

Sunset Sail, Key West, FL

No trip to Key West is complete without watching the famous sunset dip below the horizon.

Sunset Sail, Key West, FL

Most visitors head to Mallory Square for the nightly Sunset Celebration, but a sunset cruise can be a peaceful and very enjoyable way to spend your last couple hours of daylight.

Street Food, Key West, FL

Street food perfect for those late nights out on Duval Street.

Duval Street, Key West, FL

After the sunset celebration, the crowds move to Duval Street for some late night trouble.