Five things to do in Key West

These five high points in Key West ensure lasting memories of America’s most famous slice of the Caribbean. Photo: Jason Heflin

KEY WEST, February 1, 2013 — There are plenty of things to do while on the island of Key West, but checking these five high points off the list will ensure lasting memories of America’s most famous slice of the Caribbean.

Two Wheels are Better than Four

The first order of business for any Key West visitor is to find a perch upon the nearest bar stool, order a favorite drink, exhale, and adjust to island time. The next item on the agenda, however, should be to find a bike rental company. Bicycles are the best way to get around; island  traffic can be at a snail’s pace and side streets are often a tight squeeze for large vehicles.

Bicycle rental stands are set up all over the Old Town district, and prices don’t vary much. Shopping around will save only a few dollars per day, so the best bike rental company is often the one that is closest to your hotel. Pirate Rentals was our choice and had excellent equipment, provided a head light and tail light for night riding, and negotiated the price when we mentioned a cheaper fee listed on their website. One piece of advice about riding in Key West: be a defensive driver.  There are many distractions that can take a motorist’s attention off the road and an inattentive cyclist could easily pay the price.

 My Blue Heaven

Blue Heaven is an idyllic outdoor restaurant located in Old Town off Thomas Street that boasts one of the best brunches on the island. This gastronomic gem can’t be missed. Towering tropical trees shade what feels like someone’s back yard and the many lazy felines, who stretch and yawn from their vantage points atop furniture and porch railings, give it an even homier feel. The twang of acoustic guitar or the soft voice of an aspiring singer-songwriter echoes around the courtyard most mornings.

Brunch is served throughout each morning and into the afternoon. Typical indulgences include lobster and bacon omelets, spicy bloody marys, piping hot coffee, and of course key lime pie with meringue towering toward the sky. When there is a wait, the bar is a fantastic place to sit and soak up the sounds of a friendly ping-pong game, the crowing of a resident rooster, and the happy clank of glasses.

Paddling the Mangroves

No trip to the southernmost point in the U.S. would be complete without exploring the backcountry. On a small island situated in the northern Caribbean, that means mangroves.

Mangroves are a tree-like plant that grows into a tangled forest in shallow salty water. They eventually build up enough organic material to catch fresh water, support life, and even form islands. Kayaking through these twisted shady groves reveals a whole world of wildlife. Mighty pelicans and slender white egrets fly overhead while starfish, sea cucumbers, and a variety of tropical fish swim below the boat in this marine ecosystem.

Lazy Dog Kayak Guides outfits visitors with a kayak or paddleboard rental and can even set them up with a naturalist, who will provide a guided peek into this unique habitat.

Find Something Better Than Se

Key West is known for its sexy atmosphere, and for a slice of hedonism of the culinary variety, check out the Better Than Sex dessert bar. Drop by when the sun goes down and after a light meal.  Satisfying a sweet tooth is their top priority – everything, even the drinks, packs a rich and sugary kiss.

Simply passing through the doors of this corner building is sexy, since the lights are low and candles hide in every nook. The dimly lit room doesn’t hinder ordering; the menus are backlit with a soft glow that keeps with the mysterious and sexy ambience. Start the experience with one of the many craft beers rimmed in house-made dark chocolate. Follow with a peanut butter pie resting on a chocolate chip cookie dough crust and covered in sea salted dark chocolate shards. Fruity options marry the sweetness of handcrafted caramel to the bitter bite of green apple. Anyone with a hankering for a sugar high will get a fix here.

Sail Into The Sunset

Key West has some of the most brilliant sunsets anywhere on Earth, and it’s hard to argue with that once you’ve watched that orange orb sink below the surface of a glassy sea as it illuminates all the clouds above it in a spray of colors.  There’s no better place in Key West to watch the sunset than from the deck of a masted schooner during a wine tasting cruise.

With the sound of the sails flapping, chardonnay in hand, and a warm breeze blowing through your hair, this will certainly be a highlight of the trip. Sunset cruises are launched each day from Westin Marina near Mallory Square. We chose the Danger Charters Wind and Wine Sunset Sail. The captain and crew not only know the waters, but also know their wine. While the sunset is fabulous, so are the flights of white and red wine complimented by cheese, meat, and dark chocolate hors d’oeuvres. Those who don’t enjoy the fruit of the vine can choose beer, soda or water to quench their thirst. A sunset cruise is an incredible way to wrap up a stay on the southernmost point in the continental U.S.


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Jason Heflin

Jason spent his youth exploring the creeks, trails, and back roads of his home state, Kentucky. His final year in college he joined a study abroad trip to Ireland.  His time exploirng the hills and pubs of the Emerald Isle sparked his passion for  travel.  Since then, his journeys have landed him on five continents and in dozens of countries.

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