As you gaze into your 2016 crystal travel ball, imagine a getaway to one of North America’s friendliest, most fun-loving destinations. Head to the southernmost site of the U.S. – the Florida Keys & Key West – for your great winter (or anytime) escape. Enjoy blue, sunny skies, soft, sub-tropical breezes and emerald waters as you kick back, feed the fishes and sip a mojito, or two.

Book a flight directly into Key West or into Miami International Airport (MIA) to catch a shuttle or rent a car to the Florida Keys, a string of upper, middle and lower islands stretching from Key Largo to Islamorada, Marathon, Big Pine Key and finally, Key West, covering 125 miles. Highway 1 connects the Florida Keys to the mainland and the shuttle drive from MIA takes an estimated 3.5 to 4 hours (with drop-offs) at the highway’s highest speed limit of 55 mph.

Florida Keys Historic 7-Mile Bridge

For your ultimate stay and play vacation, here are a few fun activities to add to your playdate in paradise.

Voyage on the African Queen.

In Key Largo, hop aboard history with a 1.5 – 2 hour day or dinner cruise on the one and only recently-restored (2011) African Queen from the same-named classic film starring Humphrey Bogart and Kathryn Hepburn. Channel your inner Bogart and Hepburn with a turn at the helm and blow of the steamboat whistle.

Go Deep-Sea Fishing.

Continue your fun getaway with someone widely-respected as one of Florida’s national treasures, Long Island-bred Captain Skip Bradeen, who has been plying the waters of the Florida Keys for over 50 years.

Captain Skip’s musical medley on board sets an easy-living tone on his charter boat, Blue Chip Too. Apart from his mellifluous New York accent, we’re welcomed with throwback tunes like Mack the Knife, Cathy’s Clown, I’m Gonna Sit Right Down and Write Myself a Letter, and Kissing and a Hugging with Fred. 

Our afternoon mission, should we choose to accept it – and of course, we do – is to land red or yellow-tailed snapper, marlin, grouper, sailfish or possibly “shock”for our evening dinner. “What kind of fish is that, Captain Skip?” “Shock! Shock!” For a minute, we’re confused. Then we get it. “Ahh – shark!” Though the sharks elude us, by the end of our afternoon adventure, we manage to capture enough of the others to “cook our catch”  later that evening at Lazy Days Restaurant in Islamorada.

Kayak through Mangroves.

While adventure enthusiasts can follow the Florida Keys’ paddling trail from Key Largo to Key West, we opt for a shorter, alternate route through the quiet, backcountry No Name mangrove. What is a mangrove exactly? Just ask Captain Bill Keogh of Big Pine Kayak Adventures who together with his trusted canine companion leads our group of kayakers through a lush, mysterious waterway, a forested marine ecosystem for sea- and birdlife.

As we navigate through the shallow waters, paddling where possible or pulling ourselves forward on the branches dangling overhead, Captain Bill points out the abundance of wildlife all around us. It’s hard to imagine a more satisfying, peaceful way to spend an afternoon while learning about the colorful creatures who live here.

Explore Key West.

For an overview of popular sites and tourist attractions in Key West, we take the “hop on-hop off” Old Town Trolley sightseeing tour with thirteen stops along the way. Our ride includes a cruise down Duval Street, famous for its festivals and parades, shopping and bars like Jimmy Buffet’s Margaritaville, Hard Rock Cafe, Sloppy Joe’s and the Bull & Whistle.

Of course no stay in Key West would be complete for Hemingway aficionados without a visit to his home, now a museum. From the estate’s luxurious grounds with built-in swimming pool, to the purring six-toed cats that grace the premises, to a guided tour through the Spanish colonial-style home and writer’s studio, the site offers a fascinating peek into Hemingway’s life during his years in Key West. The author’s legend lives on in the fun Papa Look-Alike contest held annually during Hemingway Days in July.

Visitors can walk through a bird and butterfly wonderland at The Key West Butterfly & Nature Conservatory, another popular Key West attraction on the tour. Vibrant. Magical. Calming. Soft background music adds to nature’s sounds of cascading water and birdsong as we stroll among the tropical flora and fauna in the glass-enclosed surroundings. Exotic species of birds and butterflies fly freely around us. Occasionally a butterfly lights on one lucky visitor, while the rest of us gaze at the magnificent colors up close and personal.

You have to love a town where locals and tourists gather nightly to view and celebrate sunset as a community event. Jugglers, musicians, artisans, and psychics all contribute to the festive atmosphere that takes over Mallory Square each evening starting two hours before sunset.

Or how about a quieter celebration with a sunset cruise? So many choices, each equally fun and memorable.

Eat, Drink and Make Merry.

Hogfish Bar & Grill

Enjoy oceanfront and open-air dining at several restaurants throughout the Florida Keys and Key West. Whether having breakfast at the Morada Bay Beach Cafe or lunch at The Hungry Tarpon where you can feed silver kings from your bucket of baitfish in Islamorada; whether starting your day with huge cinnamon and sticky buns at Bob’s Bunz or having lunch at Hogfish Bar and Grill where the specialty is – you guessed it – fresh, flavorful hogfish; whether you “cook your catch” for dinner at Lazy Days Restaurant in Islamorada, check in for dinner at El Meson de Pepe, a Cuban restaurant, or Half Shell Raw Bar in Key West; whether you meet for breakfast at Blue Heaven in Key West’s Bahama Village Neighborhood (also the site of Friday-night boxing matches once refereed by Hemingway himself) or Mangrove Mama’s in Summerland Key – you can count on having fresh seafood, key lime pie and mojitos on the menu.

Key Lime Pie from El Meson de Pepe

And remember – it’s never too early in the day for key lime pie. You be the judge about the mojitos.

For more information, visit The Florida Keys & Key West.

Many thanks to The Florida Keys & Key West for the chance to experience “Prime Time in Paradise.” Some, though not all, of my expenses were covered by my hosts.

Wander on!

Nancy

What about you, wanderboomers? What are your favorite recommended experiences when visiting The Florida Keys & Key West?