Explore Key West’s Great Outdoors, Island Style

Our favorite outdoor adventures for every traveler.

Picture this: 75 degrees. Clear blue skies. Palm trees swaying to the rhythm of an ocean breeze. The perfect amount of sunshine. This is winter in Key West, our absolute favorite time of year to explore the outdoors, island style.

With a picture-perfect day as the backdrop, your choices for outdoor recreation are endless in our four-mile stretch of paradise. Whether you’re hoping to hook a trophy fish in the deep sea, reconnect with nature in the New Year, or make good on a resolution to get active, Key West has a spectacular experience to suit every traveler’s curiosities. 

Check out Parrot Key’s top picks for outdoor adventures in Key West and plan your personalized adventure! To book an experience listed below, please contact our Concierge team ahead of your arrival.


You’re stepping out from behind the screen and diving head first into adventure. We love to see it! If adrenaline is what you crave, explore our action-packed watersports packages and take your pick. 

Ready to hit the waves? Hop on your jet ski and navigate the waters as a local guide tours you around the island (and maybe some secret hideaways too.) If you dream of flying, parasailing offers incredible views of Key West’s natural beauty. Feel the butterflies flutter as you soar higher and higher above the shoreline; breathe in the stunning scenery below. 

Perhaps you have an even greater appetite for heart-pumping adventure. Think you can handle a 400-pound swordfish? Then deep sea fishing might be your match. But don’t be fooled by the leisurely wait for a bite. Once that trophy fish is hooked, you’re in for a fight. 


How about pairing your outdoor exploration with some U.S. history? 

Dating back to 1845, Fort Zachary Taylor is a National Historic Monument in Key West and home to the largest arsenal of Civil War weaponry and arms in the world. Located on 54 acres of state park, Fort Taylor played important roles in the Civil War, the Spanish-American War, WWI, WWII and the Cuban Missile Crisis. Visitors can tour the historic fort with a local guide daily at 11 am or wander on their own before retreating to the beach, a favorite locals’ spot with shaded picnic tables and grills to cook up your catch of the day.

History buffs should also venture to the Dry Tortugas National Park. Accessible only by boat or seaplane, this remote, 100-square-mile park includes seven small islands, 360-degree views of crystal clear ocean, and a fascinating history traced to Ponce De León’s 1513 voyage. Tour the impressive Fort Jefferson on foot, then jump into the water for an incredible sight. 

Below the surface lie storied shipwrecks and historic artifacts, not to mention an abundance of diverse marine life. Thanks to the park’s proximity to the Florida Keys reef system, divers and snorkelers may swim beside colorful parrot fish, reef squid, barracudas, or even the endangered American crocodile (Ok, maybe we should move this one to the “Thrill Seekers” section…) 

Finally, we can’t forget to mention Old Town Key West. Soak up the perfect winter weather as you stroll or bike through this centuries-old district, home to historic landmarks like the Ernest Hemingway Home and Museum, the Key West Lighthouse, and Harry S. Truman’s famous Little White House. 


Hiking and bird watching may not come to mind when you think of Key West. But at Fort Zachary Taylor State Park you’ll find just that and so much more. 

Budding botanists will enjoy the park’s nature trails full of native plants. Cycle through one of the park’s designated bike paths, and keep an eye out for exotic birds too – the park is part of the Great Florida Birding Trail, an excellent vantage point to watch bird migrations! 


Key West is the ultimate destination for those who are happiest on water. Across the island you’ll find endless locations for activities like stand-up paddleboarding, kayaking, snorkeling, scuba diving, boating, and swimming. (Pssst…Parrot Key guests can enjoy a selection of watersports directly on-site!)

Dolphin watching is plentiful in the Atlantic and Gulf of Mexico, and our partners at Sunset Watersports know all of the best locations for up-close encounters. 

For those who prefer to catch their fins, Key West offers world-class fishing for a range of interests and experience levels. Cast your line with expert guides and learn the tricks to inshore flats fishing, or go offshore for tournament-style game species like tuna, mahi and swordfish.


Traveling with family is, shall we say, an adventure. Luckily Key West is perfectly suited for multigenerational families, young children, older teens and everyone in between.

Our new Parrot Play package is perfect for families who want to make the most of their Key West vacation. Make yourself at home in one of our waterfront villas before venturing outdoors for a snorkeling adventure and dolphin watching tour led by our partners at Sunset Watersports

A short (and complimentary) shuttle bus away, Smathers Beach is another laid back destination for family fun in the sun. Take some of Parrot Key’s beach toys, like paddle ball and sand castle buckets, or kick off a competitive game of beach volleyball. 

How about a good ol’ fashioned treasure hunt? Embark on an on-site scavenger hunt with our Parrot Play package, or head to Fort Zachary Taylor State Park to test your skills with geocaching, a worldwide treasure hunting game in which players use GPS to hide and seek “treasure” in different locations.

Of course, some days you may just want to unwind in your own surroundings. Parrot Key has you covered. With four swimming pools, five acres of tropical gardens and delicious dining on-site, you may never want to leave. And we wouldn’t blame you! 


Ready to explore Key West’s outdoors? Take a look at our seasonal offers, and book online or contact our Reservations team to reserve your stay at Parrot Key Hotel & Villas.


Written by: Caitlin Driscoll

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