The Florida Keys have some of the finest sailing waters on the East Coast. Navigational aids in the Keys are easier to follow than in the Bahamas, where there are only a few major lights and inadequate charts. You have to read the water, which makes it difficult to move around at night or when the water is murky. In the Keys, waters are well-marked, charts are up-todate, and the Coast Guard keeps the channels dredged to the proper depth. Usually, what you see on the chart is what you’ve got under the keel, barring extreme high and low tides. The Keys are a nice alternative to the Bahamas because you don’t have to contend with international protocol, customs inspection, quarantine regulations and vaccinations, or extra insurance on your vessel.

The Keys are America’s Out Islands, with the only coral reef in the continental United States. The warmth of the Gulf Stream and seeds carried by the trade winds give them a tropical climate and vegetation. The local people are friendly. The native-born are called Conchs; others who have lived there more than ten years are called Freshwater Conchs; everybody else is a tourist.

Expert marine repair services are widely available in the Keys. If you need a replacement part, you won’t have to wait while it’s shipped overseas, or pay duty on it when it arrives. In case of emergency, telephones, medical aid and the U.S. Coast Guard are close at hand.

In the Keys you can cruise in any style that suits your taste. If you like seclusion, you can provision “Bahama Style,” with enough canned and dried food to last for several weeks spent swimming, fishing, or exploring uninhabited islands and deserted beaches. If you like fresh meat, milk, water and ice, sometimes hard to find in the Bahamas, you can return to civilization long enough to reprovision. There are plenty of supermarkets in the Keys, many within walking distance of the marinas where you can stop for fuel, water and ice.

If you prefer resort living, you can cruise from one luxury marina to another, enjoying golf courses, tennis courts, swimming pools and gourmet restaurants. Or you can go to the old fishing camps and eat freshly caught fish, shrimp and lobster while you talk to people who have been fishing the same water for thirty years. In bars and coffee houses you’ll hear old sea songs and folk music played by struggling young musicians.

The Keys are full of colorful history, from the days of the Spanish galleons and Keys-based pirates, to the time when salvage from wrecked ships furnished the homes of Key West and made it America’s richest city. The Barrier Reef, which made this one of the most dangerous coasts in the world, is now clearly marked. The U.S. Coast Guard provides weather information and immediate assistance when needed. Nowadays, the only salvagers are divers who still bring up treasure from wrecked galleons.

You’ll get plenty of cruising variety. You can go down on the outside and come back on the inside, where there’s beautiful open water for sailing and where, if the weather is bad, you can pull into shelter. I enjoy sailing in the Bahamas and the Keys. I think the Keys offer the best part of both worlds. While the Keys, like the Bahamas, are most accessible to boats with drafts up to 4 ½ feet, boats with 5 ½ or 6 feet can cruise the Keys. Every year more marinas open deep draft facilities on the Atlantic side, as cruising the Keys becomes more popular.

From Miami into the Atlantic there are several channels, but Government Cut would be the safest choice. Along Hawk Channel there are numerous places where you can stop. Even in the longest stretches, you would never have more than a 60-mile run to make in daytime, and most of the anchorages and marinas are close enough together so that you can take time to visit points of interest on shore or dive on the beautiful coral reefs along the way.

At Channel 5 or Snake Creek you can swing through Yacht Channel and go over to Cape Sable, which has some unbelievably beautiful beaches, then up the west coast of Florida, taking shelter in the Shark River or behind Sands Key for protection from the weather. At Marathon most of the marinas, on the inside as well as the outside, can handle a deep draft boat. From Marathon to Key West is a good day’s run, but you can put in at Newfound Harbor or Stock Island on the way. From Key West you can go on to Fort Jefferson and the Dry Tortugas, which are known as the Gibraltar of the South. It’s a blue-water trip that can challenge the capabilities of the vessel, captain and crew.

Boats with drafts up to 4 ½ feet have a wide variety of routes, with interesting side trips and beautiful anchorages. Most of the marinas can accommodate you. Swing from the outside to the inside to visit places of special interest or run for shelter in bad weather. If you cut through Yacht Channel to the west coast, stop at Lake Inghram on the way to Cape Sable. From Marathon you can go on to Key West in Hawk Channel, with several anchorages available along the way, or take the back route through Big Spanish Channel for a more away-from-it-all experience.

If you go on to the Dry Tortugas, 4 feet can make it inside the Marquesas for protected anchorage. Fort Jefferson is on Garden Key, where the diving is spectacular. There is a well-marked underwater nature trail, fishing is so easy it almost isn’t sport, and a chance to observe the nesting season of thousands of migrating sooty terns.

In the Keys, most marinas that accept transient boaters do so on a first come, first serve basis. However, there are no set rules and it’s safest to call ahead for reservations if you can. At the same time, you can ask the dockmaster whether there are any changes in the entrance or approaches to the marina. Privately maintained markers are subject to change without notice or often without indication on the charts.

(Editor’s note: The Keys are a 125-mile long archipelago comprising about 1,700 islands, many uninhabited and accessible only by boat. We’re focusing on areas with the most amenities for cruising sailors, or the best recreational opportunities.)

Key Largo

To reach the Atlantic side of Key Largo, you can come down from Miami through Government Cut or Biscayne Channel into Hawk Channel; or, if your draft is amenable, take the Inland Waterway and come out at Angelfish Creek. South of Angelfish Creek you pass the world famous Ocean Reef Yacht Club and the Garden Cove Marina just inside Rattlesnake Key. Their entrance is kind of shallow, but they stand by on VHF 68.

From Broad Creek to Molasses Reef, all the ocean floor under Hawk Channel is the John Pennekamp Coral Reef State Park and Key Largo Coral Reef Marine Sanctuary. Park headquarters are on Largo Sound, which is entered through South Sound Creek, south of El Radabob Key. John Pennekamp State Park is a living coral reef. You’re welcome to snorkel, dive or fish off the reef, but you must observe park regulations, which are enforced strictly. Mosquito Bank, where you’ll find coral gardens and coral heads, has a big marker. At Molasses Reef, the most fascinating thing to me is the giant coral heads. They stand in 25 feet of water, but some of them come up within 10 feet of the surface. Some of the fish you’ll see on the reef are white grunts, porkfish, sergeant majors, parrotfish, and queen, black and French angelfish. You’ll see sea fans, pink tubular sponges, spotted eagle rays and leopard rays. It makes you realize that the Keys are unique: “out islands” and coral reefs, but still part of the continental United States. At Key Largo dry rocks is the “Christ of the Deep,” a 13-foot bronze statue on 30 feet of water. It’s a beautiful and awesome sight.

At low water you can carry 4.9 feet into Best Western, Key Largo. Holiday Inn Marina is at the end of the canal, as is Marina Del Mar. From these marinas you can walk over to a large shopping center where you can pick up supplies. Many people on my charter take advantage of the numerous commercial facilities at Key Largo: Guided diving of fishing trips, sailboat rentals and rides on the glass bottomed boat Key Largo Princess. For some bargains, you can call West Marine or Boater’s World – they each have a spot in North Key Largo.

Islamorada

There are plenty of recreational facilities on either side of Whale Harbor, which separates Windley Key from Islamorada on Upper Matecumbe. The area is famous for bonefishing, and you can hire a guide, rent a boat or buy tackle. The reefs are worth seeing; you can view them from a glass bottom boat or rent diving equipment for an underwater look. On Windley Key is the Theater of the Sea, which has porpoise and sea lion shows, plus tanks of fish, including sharks.

Islamorada is the third largest city in the Keys, and a good place to reprovision or take a shore break to visit art galleries, shop for resort wear or dine in one of the many excellent restaurants. The Lorelei Restaurant Basin offers facilities for yachts and small boats, while Max’s provides marine repair and haul out service.

If you are traveling on the outside, in Hawk Channel, Windley Key is a good place to put in. A very strong current runs through Whale Harbor Channel. Be sure to allow for the set when entering Holiday Isle Marina on the north side of Whale Harbor. The marina has a 5-foot channel and 8 feet of water alongside. Facilities include beach, pool, several restaurants and an open air Tiki bar that serves the best Rum Runner Punch on the eastern shore. You can also fuel up you vessel with gas or diesel. Charter fishing boats tie up on the northwest side of the dock, where they sell the day’s catch. If you’ve been trolling Hawk’s Channel with no luck, walk over and pick up some fresh fish for supper.

Marathon

Marathon is the city; Vaca Key is the place, with a population of about 8,000. Marathon has a library, hospital, an airport and rental car facilities, as well as numerous good restaurants, shops and markets. It’s an important center for both sport and commercial fishing, and a good place to purchase fresh seafood, reasonably priced, right from the boats.

For the yachtsman there are marine supplies and several boat yards for hauling and repairs. Sombrero Reef and Washerwoman Shoal provide interest for divers. The microtowers make good aids for navigation. On the Florida Bay side, after you pass Rachel Bank, you’ll find several marinas that can accommodate boats up to 100 feet in length. All of them contain restaurants, and some offer shore accommodations and resort facilities.

Coming in from Hawk Channel, use the East Washerwoman Shoal light as a reference point, then the western tip of Knight Key, to pick up markers leading into Boot Key Harbor. This harbor is well protected, and if you don’t care to tie up at a marina, you can anchor there; check your depth carefully. Marathon is the beginning of the Seven Mile Bridge, and west of Boot Key, Moser Channel and Bahia Honda Channel (20-foot clearance) are the last cross-over spots in the Keys. If you intend to continue to Key West, you must decide at Marathon whether you want to travel on the Atlantic or Gulf side. Moser Channel has a new fixed span with a mast height clearance of 65 feet.

Bahia Honda Key

If you are taking the Gulf of Mexico route from Marathon to Key West, this is a good place to stop before heading into Big Spanish Channel. The marina at Sunshine Key is the last Gulfside marina from here to Key West. Keep daymarker No. 19 on your port side, and then follow their well-marked channel in. There is a strong setting current through the entrance to Sunshine Channel, with 4 to 4 1/2 feet of water, depending on the tide. You can get propane gas and marine supplies here while your kids take advantage of the children’s playground and teenage recreation room.

Bahia Honda State Park is only accessible to sailboats from the ocean side, through a cut in the old bridge. Powerboaters can go further west, under the fixed bridge to Bahia Honda Park Marina. The state recreational area on Bahia Honda rents out bicycles, skiffs and canoes for sightseeing. This is where the waters of the Keys take on tropical colors and variations. It’s a great help for navigation and provides interesting skin diving and snorkeling. In these clear waters we have seen green turtles, pilot whales and hundreds of porpoises feeding and playing in their natural environment.

Key West

Historic old Key West is one of the high points of any cruise of the Florida Keys. It’s a charming city with a colorful - if rowdy - past, popular with artists, writers and sport fishermen. Boating facilities are excellent and the restaurants of Key West are famous, especially for seafood, Conch and Spanish cooking. Since this is a commercial fishing area, shrimp and seafood purchased directly from the fisherman are delicious and very reasonably priced.

If you come down from Marathon on the outside, the first group of marinas is on Stock Island. Safe Harbor has an easy entrance with plenty of water for vessels up to 10 to 12 feet in draft, as you head into Safe Harbor Channel. To reach Oceanside Marina, dogleg to the east halfway up the channel. They stand by on VHF channel 16. Caution should be taken here; the rest is well-marked. The marinas offer full facilities, including repairs, and welcome transient yachtsmen. There is bus service from Stock Island to the center of the city, but you have to walk about ½ a mile to the bus stop. In the main entrance to Key West Harbor there are several areas where you can anchor in calm weather and be within walking distance of the old city.

If you follow the channel on up behind the rock jetty, you will see the Galleon Marina. They have nice floating docks – call Big John on VHF 16. Then there is the A&B Lobster House docks, Lands End Harbor walk docks, and Conch Harbor. All this is within walking distance to: Key West Bight Marina, West Marine, Pepe’s for breakfast and lunch, bait and tackle shops and The Old Schooner Wharf Bar, the last of the old town. It’s a short distance to grub and grog, shops, and Key West Marine Hardware if you need any stuff for your boat. To the south is Conch Harbor Marina, home of Florida Yacht Charters’ Key West base. If you want to go further around to the eastern side of Flemming Key, you can pick up one of the 88 mooring buoys for about 15 bucks a night.

A ride on the famous Conch Train is a good way to get your first view of the city. The Conch Train Depot is near Mallory Dock, a restored area that’s a focal point for Key Westers. Here you’ll find the Aquarium, the waterfront Playhouse and the ticket office of the old Mallory Steamship Line. The Old Island Restoration Foundation has turned this building into a Hospitality House, where you can get information about Key West’s history, attractions and artisans (handmade fabrics, jewelry, palm hats, leatherwork, musical instruments and cigars). Get a map of the Pelican Path, a self-guided walking tour of the Old Town.

A you walk out on Mallory Dock, you may be puzzled by a sign announcing the precise time of sunset for the day. In Key West, sunset watching is a daily ritual. I don’t know any other place in the world where this phenomenon occurs. If you try walking east on Duval Street at the end of the day, you may be trampled by the crowds heading west. They start gathering on Mallory Street about two hours before sundown, and the celebration really rocks the dock. If you like music in a less frantic atmosphere and have enough coins for a drink of rum, head downtown. Many singers get their start in the bars, restaurants and streets of Key West. You never know who you’ll see at Captain Tony’s or Margaritaville.

Part of Key West’s charm comes from the unique Conch architecture. The city has restoration fever, so you’ll find these old places in every condition from collapsed to brand new. Most of them are clustered in the Old Town; stroll around and admire. A few are open to the public, so you can see them from the inside. While you’re studying the architecture, keep an eye out for Key West’s exotic plants. Some of them have blown in on the trade winds from as far away as Africa, and can’t be found anywhere else in the continental U.S. Numerous gardens and museums point up the climate and character of Key West…a blend of New England, Caribbean and Spanish influences, spiced with seafaring, piracy and rum-running.

Weather in the Keys

The climate in the Keys is tropical, but around October 15 it starts cooling off. For the next two months it’s pleasant. June to September, you must be prepared for hot days, with extra precautions against mosquitoes and possible hurricanes. However, weather warning systems are great, with VHF weather reports and RDF weather which are used by pilots. Frequently, rain will stay over warm areas, such as the Gulf Stream and mainland, leaving Biscayne Bay clear.

Around December 15, fronts start moving down into Florida, which result in cool temperatures and strong north and northeasterly winds for a few days, followed by warm south and southeasterly winds. If watched closely, this can be used to advantage. Winds are strongest in January. Around February 15, the fronts begin to stall in Georgia and Upper Florida, making it hard for the weatherman to predict them. The best weather for cruising is from February 15 to the end of May.

Treasure Hunting in the Keys

In the days of the Spanish gold fleet, galleons and merchant ships set sail from Spain to the New World to gather gold, silver, tobacco, copper and weapons from Spanish colonies in South and Central America. The ships traveled along the northern coast of South America, stopping to pick up gold from Peru and then Mexico. From there the treasure-laden galleons sailed through the Gulf of Mexico to Cuba, 90 miles south of present day Key West. There, at Havana, they formed a convoy for the dangerous trip home to Spain.

The chief dangers to these ships as they traveled north to the Keys and southern Florida were the weather, with the possibility of hurricanes, the unmarked, jagged coral reefs of the Keys, and the presence of the many pirates who were based in Florida and, to the east, in the Bahama Islands.

Many of the galleons never made it past the Keys. Hurricanes sometimes wrecked entire fleets on the reefs, killing hundreds of people and spilling tons of precious cargo to the bottom of the ocean. Almost every Key, from Biscayne Bay to the Dry Tortugas has seen a gold ship wrecked on the reefs. Today, people strolling the beaches of the Florida Keys still find gold coins and small objects or jewelry washed up on shore. In fact, this is often one of the clues that lead to the location of a shipwreck. Some of the Keys’ most famous treasure hunters began exactly this way. When a beach yielded a sizable number of gold or silver coins, they looked for the treasure ship on the offshore reef.

While you may not want to take time to comb the beaches for silver coins or gold rings or swords and muskets, you will probably enjoy a visit to one of the several treasure and pirate museums located in the Keys. These museums display treasures salvaged from the sea and relics of buccaneering days on the Spanish Main.

Captain Frank Papy is the author of several books, including Sailing – Impressions, Ideas, Deeds, Waypoint for Revenge and Teach Your Baby to Swim in the Bathtub. He has written for the Yachtsman’s Guide to the Bahamas since 1981 and is the Contributing Editor to the revised 2008 edition. He’s always on the water aboard his Morgan sailboat Skybird, keeping the guides up to date. He spends summers on Fox Island in South Carolina and winters in Islamorada in the Keys, teaching sailing for Treasure Harbor Charters in both the Keys and Bahamas. Captain Frank has three rules of sailing: “Never be in a hurry,” “Don’t spit into the wind,” and “Don’t sail where the trees grow.” To order any of Captain Frank’s books, visit cruisingguidetothefloridakeys.com. ✦