Editor’s Note: Some of the information below may be out-of-date. The Florida Keys were heavily impacted by Hurricane Irma. Please visit fla-keys.com or the specific hotel’s website for updates.
The Conch Republic is a dream playground for any waterman, thanks to the endless blue waters thick with marine life. Sure, Duval Street deserves an evening happy hour stroll, but to truly connect with the heart of this multi-sport Florida-island outpost, grab a paddle, a pair of fins, a rod or a board and prepare to cut loose. Here are 10 things to do in Key West for those who love to be out on the water.
In Key West, happy hour happens as often on sandbars as it does at the line-up of booze joints on Duval Street. Sunset Sail Key West can take a maximum of six guests out of the Stock Island channel straight into blue water. From there, they anchor and set up an inflatable lily pad, ideal for cocktails and lounging. Or they can take you to a sandbar and shallow water for a different kind of rest and relaxation.
Every weekend or weeklong getaway needs a little downtime, best spent poolside. At The Perry Hotel, taking a dip means overlooking the ocean and dozens of boats at harbor. Wait staff at the Salty Oyster Dockside Bar and Grill keep you hydrated, whether you're drinking water or an adult beverage, such as the specialty Hemingway Daiquiri: freshly squeezed grapefruit and lime juice with Pilar Blonde Rum, Luxardo Maraschino Liqueur and simple syrup.
Yes, yoga alone works your core, but add water and a paddleboard, and that six-pack will appear much faster! Lazy Dog Paddle Yoga, based on A1A on the western edge of Stocking Island, offers ocean-bound om sessions three times a week: Tuesdays and Thursdays at 9 a.m., and Sundays at 8:30 a.m.
There's a reason Namaste Eco Excursions named their 32-foot vessel the Reef Geek: guide Jeff Bowman is fanatical about pointing out queen angelfish, barracuda and schools of blue tang to snorkeling guests. Not only is this local-born guide amped about identification, he'll also share info about coral restoration, the importance of mangroves to juvenile fish, or any other ecology topic in question.
Dinner doesn't get any fresher than when you reel in your own mahi-mahi, mackerel or snook during a four-hour excursion with Andy Griffiths Charters. If you're staying at The Perry Hotel, Chef Ryan Fredstorm, formerly of the Yardbird Southern Table & Bar in Miami, will cook your bounty to your specifications. However you order it, we recommend a side of the not-to-miss cornbread mash.
Spend a week in Havana, Cuba, setting sail from the Stocking Island Marina; Harmony Yacht Vacations launches bareboating charters to Cuba, typically mooring in the Marina Hemingway in Havana. It takes a full day to cross the Gulf Stream and reach the Caribbean's largest isle — giving you five days on the ground to get your fill of noshing on ropa vieja, scooping up cigars and hats, exploring local beaches and sipping daiquiris. Harmony provides a captain, a three-, four- or five-cabin yacht, and handles all the paperwork to keep the trip legal.
Snowy egrets, green herons and schools of needlefish are all likely sightings during a half-day kayaking session with Namaste Eco Excursions. Their mother ship ferries guests from Stocking Island Marina to the red mangrove forests of The Great White Heron Wildlife Heron Refuge. Paddle through mangrove tunnels to spot birds nest and sea grass beds where juvenile nurse sharks seek sanctuary.
It's rare that you can bring Max along on holiday, but in Key West, a flip-flops kind of town, dogs are more than welcome. Hotels such as The Perry allow four-legged guests in rooms on the first level. And for fun, try paddleboarding: Lazy Dog Adventures lets pooches ride along on guided tours and DIY board rentals. Guided tours are two hours of exploring Cow Key Channel and beyond.
It's hard not to be impressed when dropping down on the U.S.N.S. General Hoyt S. Vandenberg — a former Air Force missile tracking ship that has become the world's second largest artificial reef at 522 feet long. Three buoys mark the start of different dives, allowing certified scuba divers (and snorkelers) to explore clean passageways, elevator shafts, cargo holds and among the radar dishes. From the Stocking Island Marina, Lost Reef Adventures visits the wreck every week.
Key West is famous the world over for sunset celebrations at Mallory Square, formerly nothing more than an after-work hangout for locals. Now, it's a melting pot of street acts, from tightrope walkers to fire jugglers where throngs of tourists convene to be entertained. Wander the action by foot, or let Sunset Sail Key West show you another sunset experience: Their fleet of three schooners takes guests out to the blue water of the Strait of Florida for uninterrupted views of sea and a sky exploding with color — a gorgeous finale to any trip.
