Long Weekend Couples’ Trip to Key West

Just a short walk from The Marker is Duval Street. It is a 1.25 stretch north from the Gulf of Mexico South to the Atlantic Ocean. The Key West Historic District surrounds Duval Street and within this area are many interesting sites, sounds, eats, and activities.

Fort Zachary Taylor

You’ll have a full day after the roosters wake you up. Start your morning with coffee and sandwiches from the Cuban Coffee Queen, then head to Fort Zachary Taylor to explore the old fort, have lunch and relax on the beach, or head back to The Marker to spend a few hours at the pool before getting ready to go out for the evening. Spend the evening enjoying Caribbean-inspired cuisine and dancing to live music. Eating fresh seafood with drinks on Sunset Pier is a wonderful way to watch the sunset.

Sloppy Joe’s

A restaurant crawl allows you to take in an assortment of fresh seafood as well as Caribbean and Cuban-inspired cuisine. I recommend the build your own seafood boil at Stinkin’ Crawfish. The Whole Hog BBQ Nachos at Hog’s Breath Saloon are delicious! The Havana Island Cafe food truck’s quesadillas were so yummy! You can also add in a drink sampler. I recommend the Rum Runner. This is the official drink of the Conch (pronounced “conk”) Republic. The drink officially came from the nearby island of Islamorada during the days of prohibition. I also recommend the Hogarita at Hog’s Breath Saloon. It’s just a short walk back to the resort.

A long weekend is the perfect amount of time to explore this small but full island.

Studio where Jimmy Buffet recorded

Don’t forget to snap selfies and pics at the southernmost point in the United States and the mile marker zero signs.

Literary fans won’t want to miss Hemingway’s home and traveling to some of his most visited spots, like Harry’s Bar. And music fans will definitely not want to miss Jimmy Buffet’s most frequented spots. The building he used as his recording studio is right near the resort. Visit the first Margaritaville restaurant!

There are chickens roaming around everywhere. Did you know American crocodiles are more common in the Keys than alligators? Also, I didn’t know there were scorpions until I was reading the book “Turtle in Paradise” by Jennifer L. Holm. I found the book in the resort room. My son read it in elementary school as a battle of the books selection. The iguanas also range in size from tiny to huge!

The worst thing about the island is the occasional rotten egg smell of the Sargussum seaweed, but that’s really only on the south end of the island—and don’t plan to visit during hurricane season.

For more inspiration and insider recommendations, visit our Key West page.