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Enriched Cruising in the Florida Keys

by Mark and Diana Doyle

The Doyles are the authors of a cruising guide to the Florida Keys, titled Managing the Waterway: Biscayne Bay, FL to Dry Tortugas, FL. In addition to mile-by-mile coverage and interpretive vignettes, their guide also includes a Land & Sea Navigation chapter with 90 pages of annotated NOAA charts mated with annotated County land maps.

This article excerpts some of the sights and stories of the Florida Keys and some Keys-specific cruising tips from the guide’s 194 interpretive vignettes and 77 tips.

To view their previous articles about cruising the ICW, please click here.


Only in the Keys...The Underwater Music Festival, Photo by Bill Keogh, Courtesy of Monroe County TDC
Welcome to what is affectionately called the “Redneck Riviera.” This is the Riviera described with the adjective "Keysie," capturing the unique style and look of the Florida Keys. If a thesaurus listed an entry for Keysie, the closest synonyms would be “tacky” or “kitschy.” But they’re not synonyms. Keysie is tacky with a tropical panache.

Keysie is wearing flip-flops no matter what the occasion. It’s Hawaiian shirts hanging limp from the humidity. It’s $250-a-night luxury hotel room with mildewed wallboard and palmetto bugs. It’s a ride in a beat-up taxi that reminds you of and charges you only $5.

Keysie is yards with lawns of powdered marl and recycled shells. It’s a strip mall of bait shops and shell shacks overlooking million-dollar tropical vistas. Keysie is a trailer park with Christmas lights wrapped around palm trees. It’s the best grouper sandwich you’ll ever have, served with plastic silverware and beer in a go-go cup.

More seriously, the Florida Keys are a 150-mile chain of small islands and home to North America ’s only barrier coral reef. Linked by 42 bridges, these scattered islands cover almost 3,000 square miles. Technically they claim 882 islands large enough to show on hydrographic maps. Only Alaska —with its Southeast Passage and Aleutian chain—has more islands than Florida’s string of tropical keys.

Florida Keys National Marine Sanctuary

A magnificent reef, North America’s only coral barrier reef and the third largest reef system in the world, lies only four to six miles offshore. From Biscayne Bay to the Dry Tortugas , 2900 square nautical miles are protected as the Florida Keys National Marine Sanctuary.

Although some reefs or keys are closed to protect nesting wildlife, most of the sanctuary is open to visitors. The park maintains mooring buoys all along the reef line, including Hens & Chickens, Cheeca Rocks, Alligator Reef, Elbow Reef, Turtle Shoal, and Carysfort Reef. There are also additional mooring buoys near several keys, including Pennekamp State Park, Lignumvitae Key Botanical State Park, Shell Key State Preserve, and Indian Key State Historic Site.

Mooring balls are on a first-come first-served basis, identified as white balls with a blue stripe. The Sanctuary prints free color brochures, available at most local marinas or shops, showing detailed locations of moorings.

Overseas Highway, Photo by Andy Newman, Courtesy of Monroe County TDC

Florida Keys National Marine Sanctuary
305/852-7717 ( Key Largo )
305/292-0311 ( Key West)

TIP: Tropical waters mean more bottom growth. Take advantage of these warm shallow anchorages to don your mask and snorkel to scrub a section of the bottom. A little at a time keeps your hull clean and slippery through the water.

Mile Markers

Beginning at Florida City and running to Key West , the Overseas Highway is marked by mile markers. Abbreviated MM, these small green rectangular signs with white numbers partition the highway into single miles. Mile markers begin with number 126 just south of Florida City , ending at “Mile Zero” at the corner of Fleming and Whitehead Streets in Key West .

Locals use mile markers more than street addresses. If you want to find World Wide Sportsman, a huge outdoor sporting store in Islamorada, go to “MM 81.5 bayside.” This designator locates the store 81.5 miles from Key West on the Florida Bay side of US 1.

Keep track of your approximate mile marker to easily compute distances and directions to nearby locations. Simply remember lower numbers are toward Key West . If you are at MM 49.5 and want to visit Boater’s World at MM 50, you need to walk 0.5 miles along US 1 away from Key West . Conversely, if you have an address on Overseas Highway, you can infer the mile marker location from the street number. For example, the Kmart on Key Largo is at 101499 Overseas Highway, meaning it is at MM 101.5. The post office on Summerland Key is at 24700 Overseas Highway , or MM 24.7. To read the mile marker from the US 1 address, move the decimal point three places to the left.

Unfortunately, Marathon is too densely populated to maintain this numbering convention. The city of Marathon , spanning from about MM 47 to MM 54, has numbered cross streets. In this region, Overseas Highway addresses are keyed to the cross street. For example, Fisherman’s Hospital at 3301 Overseas Highway is at the intersection with 33rd Street . West Marine at 2055 Overseas Highway is at 20th Street.

The Florida Department of Transportation didn’t invent the idea of mile markers along the backbone road of the Florida Keys , the railroad originally placed these mile markers. But Native Americans marked out this route long before Flagler’s time. Hundreds of years ago, stone mounds marked every 30 miles—the distance a Native American could travel by canoe and overland in a day.

John Pennekamp

What an honor: to be the namesake of an underwater park created to save hundreds of miles of coral reefs.

John Pennekamp was a transplant from Cincinnati and an associate editor at the Miami Herald. Among his newspaper colleagues, he was admired for his belief in the First Amendment. When he refused to back down over several controversial editorials about a local judge, the case went to the U.S. Supreme Court. Pennekamp won, scoring a victory for freedom of the press.

Outside the newspaper business, his passion was conservation. In the 1940s he led the Everglades National Park Commission’s fight to save the Everglades . Afterward, he turned his attention and expertise to Monroe County ’s coral reefs. During the 1950s the reefs were being destroyed at an alarming rate. Barges harvested large quantities of coral, shells, and marine life which was sold to tourists as exotic souvenirs.

Governor Collins could preserve the ocean bottom out to Florida ’s three-mile jurisdiction, but any seabed beyond three miles was under federal jurisdiction. In early 1960 President Eisenhower agreed to Florida’s request for a land transfer, proclaiming the adjacent federally-controlled land as Key Largo Coral Reef Preserve.

Meanwhile, Pennekamp negotiated a deal with local landowners such as Radford Crane. He successfully acquired 74 acres at the southwest part of Largo Sound, providing a land base to access the coral reef. On December 10, 1960, then-Governor Collins officially dedicated the park as the John Pennekamp Coral Reef State Park, in recognition of Pennekamp’s conservation efforts in South Florida.

Florida Keys National Marine Sanctuary, Courtesy of FKNMS
John Pennekamp Coral Reef State Park

TIP: Do the shuffle! When walking in water—even close to a sandy beach—wear swim socks and shuffle your feet to spook rays camouflaged in the sand. If you lift your feet and step down, you could step on a stingray tail, which will flip up to catch you with its sharp barb.

Geodetic Marker

Wellwood Geodetic Marker, Photo by Bob Care, Courtesy of FKNMS
The nation’s first underwater geodetic marker is located at Molasses Reef, at North 25 00’ 38” and West 80 22’ 22”. Installed in 2004, the Wellwood GPS Monument marks where the Wellwood, a 400-foot freighter, went aground in 1984.

The marker does not commemorate the Wellwood, which did $6.3 million of damage to the coral reef. Instead, it is intended for scientists to plot the reef recovery plan and for boaters to check the accuracy of their GPS units, preventing further groundings.

The marker is identified with an orange-and-white spar buoy, located within a few feet of the seabed brass marker 20 feet below. The buoy lists the brass marker’s latitude and longitude so you can check the precise accuracy of your GPS instruments.


Step out of your dinghy into white silt and you may have a momentary quicksand panic attack. It’s only the surface marl, the silky white silt that sucks you in but has a hard bottom.

Marl is a unique type of deposit formed from a fine powder of shells and coral mixed with clay. When compacted it forms something akin to concrete. Its sediment gets roiled up in the shallows, giving the water of the Keys a milky look, called “whitewater” by locals.

The concrete-like base of packed marl is reassuring as you step out of the dinghy, but completely confounds a traditional burying anchor. Picture a Bruce or CQR anchor trying to set on concrete and you have the appropriate image.

TIP: When anchoring in marl country, it’s best to dive in and check your anchor set and, perhaps, improve it by hand. Try to wedge the anchor into a fracture or crevice and use plenty of chain and scope.

Indian Key

Indian Key’s plants tell its history. Tall sisal plants rise above the Buttonwoods, Prickly Pear cacti grow on the sandy soil, and feathery-leafed tamarind trees cluster in a wild grove.

All these plants are left from Dr. Henry Perrine, a horticulturist and physician who settled on Indian Key in the early 1800s with his wife, two teenage daughters, and 11-year-old son. He came to study the cultivation of tropical plants. He planted sisal, also called agave, for hemp rope and cotton for fiber. He experimented with logwood, indigo, and Prickly Pear cochineal insects for dyes. He grew mulberry trees to harbor silkworms. He planted the island with fig, mango, olive, and tamarind trees. To Perrine , the Florida Keys had great potential for commercial tropical horticulture.

Perrine lived on Indian Key during the Second Seminole War. Native Americans were enraged over a government decision to relocate them to western reservations and began attacking troops and settlements. As the news reached the Keys, settlers on remote islands fled to the community safety of Key West . Settlers on Indian Key, including Dr. Perrine and his family, remained.

It’s no mystery where this story is going. Native Americans did attack Indian Key, targeting the island for its large stores of supplies. Perrine’s wife and children survived by hiding in the turtle kraal under their waterfront home, crouched all night in salt water under the docks with only a few inches of air. When the house over their heads burst into flames, young son Henry panicked and squeezed through the stakes embedded in the mud. His mother and sisters managed to follow and they fled in a small boat, rowing with one oar to a schooner anchored by Tea Table Key. Sailors on the schooners saw the little vessel and rescued them in a whaleboat.

Dr. Perrine did not survive the raid, but almost 200 years later his plants still grow in his memory. You can visit Indian Key by dinghy from the moorings and walk the tended trails to see his plants and the abandoned village. Ranger-guided tours should resume by 2008, or earlier if the hurricane-damaged dock is repaired.

Indian Key State Historic Site

TIP: Locals simply call them “flying teeth.” But whatever you choose to call them, no-see-ums, sandflies, or gnats can crawl right through the screens! Repel boarders by spraying your screens with Shoo-fly Screen and Surface Insect Spray, available at True Val ue hardware stores such as Specialty True Val ue at MM 49 bayside in Marathon .

Looe Key, Photo by Andy Newman, Courtesy of Monroe County TDC

Looe Key

Looe Key isn’t really a key. It’s an extensive reef with both patch and spur-and-groove formations. The reef’s namesake, the HMS Looe, sank here in 1744.

With 7,000 years of coral growth, including slopes, ledges, and a cave, Looe Key is described as the most beautiful reef in the Keys. It’s home to elkhorn, brain, and star coral; sea fans and whips; lobsters; octopi; and rays.Nearby the Newfound Harbor Marine Institute, or Seacamp, offers marine education including SCUBA certification.

To support the region’s coral reefs, consider joining Reef Relief, a nonprofit group based in Key West. This organization monitors several reefs and works to remove marine garbage. It has education centers in Key West at 328 William Street and on Green Turtle Cay in Abaco, Bahamas.

Looe Key National Marine Sanctuary


Seacamp/Newfound Harbor Marine Institute

Reef Relief

TIP: To pull out a stubborn anchor, first try snubbing the rode up tight and waiting with the engine idling. As you reach a 1-to-1 scope, your anchor will start to work itself out as you strain on the rode. When you start “dragging,” just pull up the anchor and engage gear.
(For more anchoring tips, click here.)

Gibraltar Of The Gulf

Fort Jefferson, Dry Tortugas , Photo by Andy Newman, Courtesy of Monroe County TDC

Fort Jefferson, located on Garden Key in the Dry Tortugas , is an outpost in the Gulf. Construction of the fort began in the 1840s and continued for over 30 years, but this hexagonal citadel was never completed. Eight-foot-thick brick walls rise 50 feet, protecting facilities for a 1,500-man garrison.

According to a story recounted by Keys historian Jerry Wilkinson, the fort’s only encounter during the Civil War was when a Confederate ship entered the harbor and demanded the fort’s surrender. The fort’s commander replied to the Confederate messenger, “Tell your captain I will blow his ship out of the water if he is not gone away from here in ten minutes.” The bluff worked: Fort Jeff never fired a gun in action during the war.

By 1861 it became a prison for Union Army deserters and Confederate war prisoners, including Dr. Samuel Mudd, the doctor who set the broken leg of John Wilkes Booth, Abraham Lincoln’s assassin. Mudd spent two years in a dark cell, which you can visit. He was pardoned in 1869 for his help during a yellow fever epidemic that overtook the fort.

If you walk around the moat, you may notice some of the walls have weakened and are peeling and dropping. This is due to the iron built into the walls around each cannon port or embrasure. The iron expands as it rusts and pushes the outer bricks from the walls. Some sections are closed to visitors, as a scheduled $16 million masonry restoration proceeds.

Dry Tortugas National Park


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