Metro Weekly

Key West: 12 “Must Dos”

6. Watch the sunset

Key West’s boasting about being home to the best sunset in the world is not just a marketing gimmick. The sunsets in Key West rarely disappoint, and watching one is practically the island’s official sport. Each evening hundreds of visitors gather with locals in Mallory Square to watch the sunset into the horizon of the Gulf of Mexico.

Photo by Troy Petenbrink

Photo: Troy Petenbrink

The ritualistic celebration includes unique street performers, musicians and food vendors. Another popular gathering place is the Sunset Pier at the Ocean Key Resort & Spa. For added adventure, a sunset cruise is also an option with Danger Charters’ Wind and Wine Sunset Sail and Schooner Western Union as two of the best.

7. Take a trolley ride

Do you know where Pulitzer Prize-winning playwright Tennessee Williams lived in Key West? How about the site of The Monster, a popular gay bar in the ’70s and ’80s? The answers to these and many more questions about of Key West’s rich LGBT history can be found on the weekly Gay Key West Trolley Tour. One of the first LGBT city history tours and certainly one of the longest continually operating, it’s given every Saturday afternoon and takes approximately 90 minutes.

Photo by Troy Petenbrink

Photo: Troy Petenbrink

Gay Key West Trolley Tour
Sponsored by Gay Key West & The Key West Business Guild in partnership with Historic Tours of America.
(305) 294-4603.

8. Play in the water

With the Atlantic Ocean to its east and the Gulf of Mexico to its west, Key West offers some of the best opportunities for water sports and play. Barefoot Billy’s offers a fun jet ski tour of the island, and Fury Water Adventures has some cool  “do-it-all” packages that include snorkeling, parasailing, jet skiing, water toys and kayaking. The Blu Q specializes in men-only catamaran tours, including a number of very popular clothing-optional sails.

Photo by Troy Petenbrink

Photo: Troy Petenbrink

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Troy Petenbrink is Metro Weekly's contributing writer for food and travel. He can be reached at

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