Smugglers Run

Looping around South Florida was not possible until the Okeechobee Waterway (OWW) was created in 1937, cutting a route through the center of the state. This project connected Lake Okeechobee (the second largest lake contained wholly in the U.S.) to both coasts by channelizing the St. Lucie River on the east and the Caloosahatchee River on the west and adding five locks and dams, maintained by the Army Corps of Engineers. This 117-mile route opened a more efficient shipping route, allowing product to be moved across the state without ships going all the way around the Florida Keys.

With water as clear as gin, dawdling can become a habit in and around Hawk Channel, the outside route through the Florida Keys.

For the recreational mariner looking to start the Florida Mini-Loop, entering the OWW is straightforward from the Intracoastal Waterway (ICW) in Stuart, Florida. After two easy lock passages, you enter Lake Okeechobee. Crossing the lake is easy in decent weather and even if the weather isn’t perfect it’s not terribly difficult. Spend the night at Roland Martin’s Marina on the southwest edge of the lake in Clewiston. If the Tiki Bar at Roland’s doesn’t suit your style for dinner, head to the Clewiston Inn. Designated as a National Historic Landmark, this classical revival–style inn built in 1938 will take you back to the days of the Sugar Barons.

And if Roland’s is full, press on a few miles farther through the first lock on the Caloosahatchee to Moore Haven (population 1,680), where you can tie up at the Moore Haven City Docks.

After winding through fragrant orange groves and miles of sugar cane fields, the OWW ends in Fort Myers. You can’t beat the facilities at the Fort Myers Yacht Basin—or its location. This municipal marina is adjacent to Centennial Park and a short walk the historic downtown River District with dozens of great restaurants and plenty of history. Fort Myers was once the winter playground for Henry Ford, Thomas Edison and Harvey Firestone. Back then the billionaires camped out together and worked together to solve America’s problems.

Located near Florida’s southern tip, Everglades City is the gateway to the Ten Thousand Islands.

Paying attention to the weather, head south along the Gulf beaches of Fort Myers and Naples. Your next adventure should be Everglades City. Once a hotbed of drug smuggling, in 1983 nearly half the population of this tiny city went to jail as part a huge federal drug bust. The Rod and Gun Club has nearly one-eighth mile of side-tie in a very protected dockage. The old hotel and restaurant have seen better days, but it is worth the visit to the wood-paneled lobby with its vintage hunting lodge atmosphere just to step back in time. Skip the Rod and Gun club for dinner, though, and instead try the stone crabs and smoked mullet dip at the waterside City Seafood. The beer is plenty cold.

Heading south at displacement speeds your next stop is Shark River. You are in the heart of darkness as far as South Florida goes. With an easy entrance and great holding, this protected anchorage has superior fishing. Hang out awhile and then head south to Key West.

The southern terminus of U.S. Route 1, Key West is literally the end of the road for land travelers. But it’s only the midpoint of your Florida Mini-Loop adventure. Key West has good anchorages and tons of dockage. At the very least rent a bicycle and tour the town that Ernest Hemingway declared second only to Havana. Key West has a higher density of great restaurants than any other place I know in the U.S., and I suggest you hit El Siboney for great Cuban food.

The Florida Mini-Loop is replete with cozy marinas and anchorages along the way—perfect for aspiring loopers looking to hone their skills.

To head north along the Keys, you can either take the “inside” route through Florida Bay or navigate Hawk Channel on the ocean side, depending on the weather. In strong northers the “outside” (ocean side) route can be a better deal at times as it keeps you on the lee side of the islands. My preference is to be inside from Bahia Honda Key to points north to hit my favorite watering holes like the Zane Grey Lounge above World Wide Sportsman in Islamorada; the Caribbean Club, where Humphrey Bogart filmed Key Largo; and Alabama Jack’s, a dinghy ride from your anchorage in Card Sound.

BONUS PHOTOS | Have a closer look at the sights along the Florida Mini-Loop in the expanded gallery below:

With the skyline of Miami on the horizon, Biscayne Bay is a beautiful place to spend some time between the wilderness of Elliot Key and the beat of Coconut Grove, Calle Ocho and the Miami Waterfront. Here you’ll find more highlights of smuggling history. A dinghy trip up the Miami River takes you to where a barge loaded with 10 tons of marijuana traveled undetected in broad daylight. To top that, a Cuban gun boat with defecting navy crew—and 50-caliber machine guns mounted on deck—once parked unnoticed in the Miami River for five days. Everybody thought it was part of a movie set.

The last stretch north can be a trudge through the bigger cities (Fort Lauderdale, Boca Raton, West Palm Beach), but still interesting. Tying the knot back in Stuart completes the loop. It’s the only opportunity to be on the ICW for several hundred miles and end up where you started, never backtracking or covering the same ground twice.

Today smuggling still goes on with everything from cocaine, cigars, rum and orchids being brought in. Timeless on one hand, ever-changing on the other. Welcome to South Florida.

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LAKE OKEECHOBEE FLORIDA MINI-LOOP HAWK CHANNEL FLORIDA KEYS SMUGGLER'S RUN