For nearly two decades, paddlers have gathered at the southern tip of Florida each year for a 12-mile group paddle around the island of Key West. The 2016 edition of the Key West Paddle Classic will take place on April 30 and May 1. While the event still centers around the circumnavigational paddle, it’s grown over the years to it include a 4-mile open race plus an assortment of other activities, clinics, demos and off-the-water fun.

Sue Cooper, owner of local paddling outfitter Lazy Dog Adventures and author of Millionaire in Flip Flops, says of the paddle around Key West, “If you can paddle it, you can race it! It's open to all self-powered vessels: stand up paddle boards, kayaks, outrigger canoes, row boats, prone paddle boards, surf skis…"

Cooper paddled in the first iteration of the race, 19 years ago.

"I was lucky enough to participate in the first annual paddle around the island in June 1998 in a single kayak with about twelve other participants. Now we have over 300 racers for the weekend. The following day, May 1, we’ll have a kids clinic, a kids race, sprint races, and a relay race. We also have some of the top racers in the country come in to host paddle clinics."

Demos and clinics at the Key West Paddle Classic. Photo courtesy Lazy Dog Adventures.

Demos and clinics at the Key West Paddle Classic. Photo courtesy Lazy Dog Adventures.

It's a welcoming race and a great way to see Key West.

"The race is a National Race for the World Paddle Association and open to all. It starts off the beach on the ocean side, takes you through the harbor then out to the Gulf of Mexico side of the island, through the channel separating Key West from the rest of the islands and back to the ocean."

Map of the paddlers' route. Courtesy Lazy Dog Adventures.

Map of the paddlers’ route. Courtesy Lazy Dog Adventures.

Even the water welcomes you. "It is beautiful, clear, and warm," says Cooper.

And you'll get to see Key West's history while circling the island, including “the beach, Southernmost Mansion, Southernmost House, Lighthouse, Mallory Square, Historic Seaport District, Harbor, Navy Station, Civil War forts, and so on."

After circling the island, be sure to plumb its interior. Bicycling is a nifty way to do that. Not only is a car unnecessary, but why would you want to climb into a steel and glass box when you're at Key West? Bikes can be rented at We Cycle (305-292-3336). Beach Cruisers are just $10 a day, and tandems are $17 per day. Once you're rolling, visit the house where Tennessee Williams took a break after creating Blanche DuBois: 1431 Duncan Street. Robert Frost was a snowbird too and he sipped conch chowder at the Casa Marina resort, which you too can do. Of course, Hemingway's Spanish colonial villa also awaits you.

Papa Hemingway loved to fish. If you do too, Key West is a great place to cast a line for tarpon (Silver Kings), a tail-walking, big-scaled, silver torpedo. Hooking tarpon isn't uncommon; landing one is more difficult due to the species’ great strength and aerobatics. If you're looking for savvy council, Capt. Brice Barr of Double Down Sportfishing (305-304-2314, knows every cay and bay. Double Down offers trips aboard a spacious 40-foot sport fishing charter boat specializing in offshore, reef and wreck fishing using live bait and light tackle.

Paddlers circumnavigating Key West. Photo courtesy Lazy Dog Adventures.

Paddlers circumnavigating Key West. Photo courtesy Lazy Dog Adventures.

Of course, vittles abound as well. Key West latitudinal and longitudinal coordinates are tart and creamy, which is why it's the home of the Key Lime pie. Want some tasty crepes, both savory and sweet? La Crêperie Key West ponies up ratatouille (onions, zucchini, tomatoes, eggplant, and peppers fried and stewed in oil) and caramel au beurre sale (salted caramel). If you want to sample island-style cooking, which is steeped in freshness and simplicity, there's The Flaming Buoy. This seafood marinara exemplifies that sensibility, with grilled key west pink shrimp and fresh catch folded through a gremolatta tossed penne pasta. Yum!

If, after The Flaming Buoy, you want more flaming boys, Key West's drag culture brightens the night. You can spend an evening enjoying performers’ impersonations of Bette Midler, Cher, and Lady Gaga at the La Te Da cabaret.

However, if you want to stay outside, there's the Key West tradition of celebrating the island’s fantastic sunsets. Mallory Square serves up the sunset carnival style. If you want to dine while gazing, there's Latitudes Restaurant and Louie's Backyard. If you prefer picnicking for the sunset, there's Fort Zachary Taylor State Park Beach.

With so much inland, don't forget the sea. Twisty mangrove thickets are fun to explore by kayak. Dolphins and turtles are ubiquitous. Manatees are less common that far west, but they can be seen, especially in the winter.

If you're there for the race, a room block is available at both The Sheraton Suites Hotel and the Best Western Key Ambassador. Cooper also recommends the Wicker House guest house. Of course, you can rent kayaks and paddleboards at Cooper's Lazy Dog Adventures. If you're at Lazy Dog, good grub is nearby.

"Our shop is located at Hurricane Hole Marina and we have a great restaurant with dockside dining. Some of our other favorites include HogFish, Turtle Kraals, and Santiago's Bodega."

Just get to Key West and you too will feel like a millionaire in flip flops.

— Learn more about the Key West Paddle Classic.

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