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Inspired by Samantha Brown: Key West & The Florida Keys Road Trip

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Samantha Brown Media
Key West, the southernmost city in the continental United States, is known for its subtropical climate, Bahamian architecture and its longstanding history as a popular retreat for artists and writers.
Courtesy of Ernest Hemingway Home and Museum
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Day 1: Arrive in Key West
Check into your hotel and prepare to experience Key West—considered paradise for many. Enjoy authentic Cuban food at El Siboney, then head to the Rum Bar in the historic Speakeasy Inn for a rum runner, the house specialty. A visit to Key West is not complete without a stop at the Ernest Hemingway Home and Museum, where you can tour the 1851 Spanish Colonial-style home of celebrated resident and author Ernest Hemingway. Visit the Key West Lighthouse Museum to learn about Florida’s lighthouse history through exhibits and audio stories about the lives of the keepers who kept the light burning since 1826. Follow Samantha’s footsteps on a literary tour past the home of Tennessee Williams. Considered one of the greatest 20th century playwrights, he called the island of Key West home for over 30 years. As the original café in the chain, Jimmy Buffett's Margaritaville—the capital of Margaritaville—is where it all got started.
AAA/Inspector 52
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Day 2: Discover More of Key West
Today, take time to appreciate the sandy beaches and marine life in Key West! Snorkel two different tropical reef locations in one day with Fury Water Adventures Double Dip Reef Snorkel. Their high-speed, state-of-the-art catamaran will get you to the reefs quickly and comfortably, cutting down on travel time and giving you more time to explore the underwater marvels. Explore Key West Aquarium, one of the very first open-air aquariums (it opened in 1934). Fish, shark and turtle feedings take place daily, and a touch tank lets visitors interact with the marine life. Duval Street is another must-do when in Key West. Stroll down Duval Street and its side streets, where neat cafés and open-air restaurants serve foods ranging from gourmet specialties to ethnic snacks. Then follow Samantha’s steps seaside to Fort Zachary Taylor Historic State Park. From there, visit the Harry S. Truman Little White House, the summer home of President Harry S. Truman while he was in office. The Hog's Breath Saloon offers authentic charm and is a reflection of the way the Florida Keys used to be. The marina-front eatery serves up fresh, delicious seafood dishes.
Samantha Brown Media
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Day 3: Off to Marathon
The midway point between Key Largo and Key West, Marathon is the largest city in the Florida Keys. Take a day trip to Marathon on your last full day in the Keys. Arriving in Marathon, learn as Samantha did about the amazing rescue work done at The Turtle Hospital. Educational programs run daily on the hour from 9 a.m. to 4 p.m. On “Samantha Brown’s Places to Love,” Samantha meets lionfish huntress Rachel Bowman, who makes a living catching this invasive species and supplying her catch to local restaurants such as Sparky’s Landing. Visit Sparky’s for yourself and savor the lionfish tacos. Crane Point Hammock Museum and Nature Center is a natural history museum featuring models of marine life, animals and birds in naturalistic settings. Guided trolley, kayak and paddleboard tours are available (reservations are recommended).
AAA/Janet Brindle Reddick
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Day 4: Say Goodbye to the Florida Keys
Before you leave Key West, you must visit Blue Heaven Restaurant & Bar and fill up on a hearty breakfast. This casual eatery has been host to such venues as cock fighting, boxing matches, billiards, a dance hall and even a bordello.