Fun Adventures in Key West for Free Spirits & Creatives

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Are you a free spirit looking for things to do in the Florida Keys? Contributor James Ross shares this list of fun adventures in Key west for free spirits to enjoy

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Chickens still cross the road here, dodging tourists and trolleys to get to the other side. I remember them on my last visit, as a student escaping a Canadian winter some 40 years ago. Then, like now, I was in search of fun adventures in Key West.

While Key West may be getting a little more upscale, the place still has not lost any of its funky, renegade charm. I loved the laidback feel of this once sleepy hideaway and was afraid that might have disappeared, so the chickens are a welcome sight.

The streets are busy, a mix of tourists and locals walking along the palm-lined streets and enjoying the old-world charm of a place that’s known for being the coolest, most eclectic city in America. Soon I’m joining them, heading out to enjoy a few fun adventures in Key West of my own…


Fun Adventures in Key West for Creative Free Spirits

Visit The Hemingway Home and Museum
Hemingways Typewriter adventures in Key West
Hemingway’s home features many exhibits relating to the author’s adventurous life (Photo: James Ross / Riley)


A large portion of Key West is a designated historic district with architecture dating to the 19th and early 20th centuries. Homes, both grand and modest, sport plantation shutters, wrought iron railings and charming verandahs, a style imported from the Bahamas.

One of these lavish homes housed the Keys’ most famous resident, author Ernest Hemingway, from 1931 to 1939. Fun guided tours of the home are a must do for any fan of literature. Highlights include the swimming pool, writing studio, and garden, complete with its stone urinal, which Hemingway claimed ownership of and took home from his favourite Key west bar, Sloppy Joes.

His studio, where literary miracles were spun, is exactly as he left it. You’ll also see about 50 ‘Hemingway cats’ roam throughout the lush grounds. Visit this popular Key West attraction’s website at


Enjoy a Hemingway Food and Drink Adventure

For those who share Hemingway’s appetite for Key West life, Key West Food Tours now offers a “Hemingway Experience” tour, an historic journey around picturesque Old Town. The guided tour enables participants to explore the island and its cuisine and libations through Hemingway’s eyes.

The Cuban food, and especially the rum, certainly leave me inspired. Ever since Hemingway made his home here in 1931, followed by other literary luminaries like Robert Frost and Tennessee Williams, and more recently Annie Dillard and Judy Blume, Key West has been a refuge for free spirits and creative individuals.

Learn more at


Take a Tour of Old Key West and its Attractions
Trumans White House oone of the best adventures in Key West
The Truman White House is easy to get to on foot or by bike or scooter (Photo: Bryan Dearsley / Riley)


An excellent way to tour the town is on an Old Town Trolley Tour, which offers transport to the town’s most popular attractions. Or you can get more adventurous and rent a bicycle or a motor scooter to get around. The island is only four miles long and 2 miles wide, so it’s easy to explore,

However you decide to do it, your adventures in Key West should include stops at some of its other popular tourist attractions. History comes alive at the Key West Shipwreck Museum. Nearby, Mel Fisher’s Maritime Museum shows off the gold coins and treasure salvaged by Key West’s most famous treasure hunter, while a short stroll away you’ll find the Little White House, the opulent Key West winter home of President Truman.

At the Key West Butterfly Museum, visitors can stroll through an inviting environment filled with hundreds of beautiful winged creatures, an impressive collection of flowering plants, colorful birds, cascading waterfalls, and tropical trees.


Explore Fort Zachary Taylor Historic State Park
braden-egli-Fort Zachary state park at sunset with ship in distance-unsplash
Fort Zachary is great spot for swimming, kayaking, or just kicking back and relaxing (Photo: Braden Egli / Unsplash)


For some relaxation and some beach play, head to Fort Zachary Taylor Historic State Park. Florida’s southernmost 56-acre state park is known for excellent snorkeling, swimming, and nature trails.

Fort Zachary Taylor, named after President Zachary Taylor, was built from 1845 to 1866, one of 47 bastions built to defend the nation’s southeastern coastline. The fort played important roles in both the Civil War and Spanish-American War and was designated a National Historic Landmark in 1973.


Participate in Fun On-water Adventures in Key West

You haven’t truly experienced Key West until you’ve been spent at least a little time on a boat. To get out on the water, Sebago Watersports offers amazing catamaran and schooner sailing tours.  

Some of the best options will have you snorkeling the reef, kayaking or parasailing. Learn more from


Enjoy a Slice of Key Lime Pie
Kermit's Key Lime Pies man holding pie
Kermit’s is the place to visit in Key West for a piece of their famous Key lime pie (Photo: James Ross / Riley)


Island cuisine offers fresh seafood, including stone crab claws, spiny lobster, and yellowtail snapper, as well aa Caribbean flavors… and Key West charm. A slice of key lime pie, the Keys’ signature dessert, is a heavenly end to any meal.

There isn’t much debated about the world of politics here in Key West, but what is hotly contested is whether the region’s well-known and prized desert, the signature key lime pie, should be topped with whipped cream or meringue. I found both delectable in my research, even the strange chocolate-covered key lime pie on a stick.

To learn all you need to know and more about the Keys’ famous desert, head to the waterfront to meet Kermit Carpenterof Kermit’s Key Lime Shop.


After Dark Adventures in Key West
The Florida Keys are famous for its Sunset adventures in Key West
Key West is famous for its spectacular sunsets and nightlife adventures (Photo: James Ross / Riley)


After a day of exploring and adventure, it’s time to watch that iridescent sun melt into the blue sea. While artisans peddle unique handicrafts on the docks of historic Mallory Square, jugglers, acrobats, fire-eaters, stilt walkers and performing cats draw applause from sunset revelers celebrating a daily ritual that never seems to disappoint.

The nightlife is also a spectacle not to be missed, a mixture of cultures, rhythms and lifestyles. As it was when I first visited this place as a student those many years ago, Duval Street is the hub. Yes, it’s a bit wild, but that’s part of the charm.

Grab a stool at Sloppy Joes and raise a glass to Hemingway. Then head off to check if they replaced the toilet facilities he took home with him.


Enjoy a Romantic Overnight Adventure in Key West

When it comes to romantic getaways, Key West doesn’t disappoint. Here are a few of our favorite luxury accommodation options that are perfect for couples:

Kimpton Winslow’s Bungalows – Nestled on the quiet end of old town, Winslow’s Bungalows features 85 guest rooms, three pools, a poolside bar, daily complimentary continental breakfast, and a bike share program. The boutique hotel’s location, known for the many historic buildings across the grounds, is walkable to all of the nightlife, museums, activities, shopping and dining Key West is known for. For reviews, rates, and reservations, visit Kimpton Winslow’s Bungalows.

Artist House Key West – This attractive Victorian-era guesthouse is ideally located close to Duval Street and is just a short distance from historic Old Town. Boutique-style accommodations feature antique furnishings and comfy beds. For reviews, rates, and reservations, visit Artist House Key West.


Have a Key West Foodie Adventure

Dining in Key West is a foodie fantasy. Here are a few favorite Key West restaurants and eateries to sink your teeth into:

Conch Republic Seafood Company – This popular eatery is located in a former fish house building in the Key West Historic Seaport overlooking a working marina. The menu is based on local and Caribbean seafood with specialties such as conch chowder, blackened Florida Keys shrimp and baked oysters callaloo. Visit to learn more.

First Flight Island Restaurant & Brewery – First Flight Island Restaurant & Brewery is located in the heart of downtown Key West. It’s well known for being the birthplace of Pan American World Airways since the structure now located at 301 Whitehead St was the place where Pan Am’s first tickets were sold in 1927. Check out their website at

Bistro 245 at Opal Key Resort – Enjoy casual dining with breathtaking views of the Key West Harbor. Fresh pasta, Black Angus beef, and Key West shrimp are just a few favorites. The restaurant serves breakfast, lunch, and dinner as well as Sunday brunch with complimentary champagne service. Visit Opal Key Resort for the latest reviews, rates, as well as room reservations.

Blue Heaven – Home to the most “heavenly” breakfast in Key West (think seafood eggs Benedict and homemade banana bread), this shuttered blue building has a century-old history of entertaining islanders on Petronia Street in the historic Bahama Village neighborhood. Through the years, the venue has hosted cock fighting, gambling and Friday-night boxing matches refereed by Ernest Hemingway. Today, diners enjoy Keys, Caribbean and seafood specialties and memorable meringue-topped Key lime pie. Learn more at


Just the Facts: Getting There and More Info

Thinking of flying to Key West? Direct flights or connections to Key West International Airport are available from many cities or fly into Miami or Fort Lauderdale-Hollywood and rent a car to drive the Florida Keys south to Key West.

Prefer to drive from Miami to Key West? Great idea! A journey of 159 miles, it’s one of the most iconic must-do drives in the USA. You can learn more about this epic adventure on Florida Keys Road Trip – From Key West to Key Largo.

Looking for more information related to these and other great adventures in Key West? Visit the Florida Keys & Key West’s official tourism group at




Contributor James Ross is a travel writer and columnist, and author of the books Cottage Daze and Still in a Daze at the Cottage. He lives in Muskoka, Ontario, Canada.

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