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.

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

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

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

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

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

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

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.

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

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

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

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

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

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

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

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.

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

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

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

How far are you from Key West?

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.

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

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

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

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

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

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

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.

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

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 perfect for those late nights out on Duval Street.

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