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Road trips don't come more spectacular than the Overseas Highway. Sailing through tropical savanna over the Florida Straits, it links Miami on the mainland with the 180-kilometer-long Florida Keys island chain.

One of the most notable people to live in Key West was writer and avid traveler Ernest Hemingway, and as a visitor you can still find many traces of Hemingway in Key West.

More than an hour’s drive south of Miami, Islamorada in the Upper Florida Keys has a history of reinventing itself. Practically annihilated by the 1935 Labor Day hurricane (still considered the strongest to reach landfall in the United States), this “Village of Islands” became known for quality sport fishing, attracting professional and amateur anglers from around the world.

Whether you’re taking a quick trip down from Miami, flying in for a short getaway, or visiting with plans to make your way through the rest of the Keys; Key West is the perfect launching point for a road trip through the Florida Keys.

The Florida Keys attract a cast of irreverent, lively characters and denizens – independent folk who embrace the perks of island living. Perhaps that’s why the Keys became the “Conch Republic” in 1982, succeeding with secession where none did before.

From Key Largo to Key West, it’s easy to fill sunny days with outdoor sports, and star-studded nights with food, drink, and downtime anywhere along this 110-mile-long island playground. Average daytime temperatures in Key West sit at 81.9 degrees—perfect for water activities. Even in the late evenings, temperatures rarely dip below a mild 73. Starting out from Miami, you can drive the length of the Overseas Highway in about four hours, but why rush when there are so many ocean views to ogle, land to explore, and fruity drinks to sip.

I recently headed to the Florida Keys so that I could cross off the three dives sites from that area, on my list of the top 100 dive sites in the world: The Vandenberg Wreck, the Spiegle Grove Wreck and Molasses Reef. All were awesome and worthy of such a list, and this post will highlights a few photos from The Vanderberg! I dove with Dive Key West Inc, which was great because they had an awesome guide, as well as a sweet boat for the hour long trip to the wreck. 

Hello World! Little Sis Rachel here with a recap from my latest adventure on behalf of Angie Away. I recently took a break from my super glam life of college summer classes, velociraptor handling in the Central Florida heat and house hunting to experience the Florida Keys.

I’m usually very efficient and organized, but for some reason I just couldn’t get my life together the week of the trip. What should’ve been a simple adventure almost didn’t happen…

In the early 1930s, famed author Ernest Hemingway began spending his winters in Key West, Florida and soon after, purchased a home where he would later write one of his many acclaimed novels, To Have and Have Not. Eighty years later, Hemingway’s presence is still hard to miss when visiting the island. Images and mentions of the burly writer can be found everywhere, from museums to gay bars. 

Can you beat sitting two thousand feet over a gorgeous turquoise ocean, peering down at more turtles than you thought existed, and listening to Tom Petty belting out “Free Falling”?.

Maybe. But for me, it was a perfect moment. Let’s rewind to the beginning, and do some word association.