Sailing the Florida Keys is full of wonders if you take the time to explore. The Keys are a boating paradise with a subtropical climate and SE winds most of the year. There are wonderful fishing, snorkeling, and diving destinations all within a day’s sail.
The Dry Tortugas, a US National Park made mostly of open water and 6 small islands, is 70 miles west of Key West. This destination features pristine water, coral reefs, and the historical Fort Jefferson.
A barrier reef runs 221 miles along Florida’s southeast coast from Key Biscayne to the Dry Tortugas. It is the only living coral barrier reef in the continental U.S. and is the third largest coral barrier reef system in the world. The reef is protected as an underwater state park known as the John Pennekamp Coral Reef State Park, the first underwater sea park of its kind.
Stephen and I along with many friends have cruised the Keys many times as well as driven from Miami to Key West on several occasions. We discover a new gem each time we venture into the Florida Keys. The Florida Rambler is a great guide of all the places of interest in the Florida Keys, mile marker to mile marker, all across the Overseas Highway! Be prepared to see unusual sights like Perky’s Bat Tower on Sugarloaf Key, Jules’ Undersea Lodge in Key Largo, and the Seven Mile Bridge.
On our most recent sailing cruise down the Florida Keys to Key West, we were positioning to sail to Cuba as a part of a rally to build relations between the sailing communities in the States and Cuba. Here are a few highlights from our most recent sail down the Keys:
Biscayne Bay & No Name Harbor
We set off from Fort Lauderdale to Miami and spent several days in No Name Harbor, our favorite anchorage in the area. The harbor is only about 2 NM from the bright
lights of Miami, but it feels like you are a far removed from all the hustle and bustle. It is a natural harbor, is well protected, and it is an easy dinghy ride out to the bay where one can kiteboard, fish, snorkel, and swim in crystal clear water. We frequently see dolphins, turtles, and manatees in the anchorage and sunsets are spectacular.
Biscayne Bay is a beautiful and protected sailing area with several anchorages like Elliott Key Marina or Dinner Key. Marinas include Bay Side Marina (downtown Miami) or Miami Beach Marina. There is a lot to explore in Biscayne Bay National Park including the Cape Florida Lighthouse at the mouth of Biscayne Bay. It was first lit in 1825 and reconstructed in 1846. It is at the end of Key Biscayne in the Cape Florida State Park. A visit to the lighthouse, the nature trails, and the beach is a treat.
Biscayne Bay is also the site of Stiltsville, the famous pastel-colored houses on stilts. Stiltsville is somewhat mysterious with a history that dates back to the 1930s, when “Crawfish Eddie Walker” built the first shack on stilts above the water. Stories of illegal alcohol and gambling abounded during its heyday as it was the playground for the cream of Miami society. Today, only seven of the houses remain after hurricanes, fires, and neglect saw many of the houses demolished.
Miami Beach and Coconut Grove are just a stone’s throw away. Exploring Miami Beach is high-octane fun, especially the famous Ocean Drive where you can rub shoulders with the rich and famous and a tour of the art deco buildings is a must!. Also close by is Little Havana, the vibrant and colorful center of Hispanic culture in Miami and the best-known neighborhood for Cuban exiles in the world. Its festivals, including the Calle Ocho Festival and Viernes Culturales (Cultural Fridays) are world famous.
Coconut Grove is a tropical oasis with a distinct Bohemian flair. Founded in 1873 by an eclectic mix of pioneers, artists, intellectuals and adventurers, it thrives to this day with charming boutiques, sidewalk cafes, and a large, very active sailing community.
No Name Harbor is a stopover for many cruisers before sailing to the Bahamas or the Caribbean.
More on Stiltsville and Diving the USS Spiegel Grove
Some of our favorite liveaboard vloggers shared an awesome video that gives you more details about Stiltsville and a dive on the intriguing wreck, USS Spiegel Grove.Hawk’s Channel and the Middle Keys
The Little Grecian Rock Reef in Hawk’s Channel is good for snorkeling, although not the best on the barrier reef. But this is where you will see the famous 
Christ of the Abyss statue, an 81/2 foot, 4,000 pound bronze sculpture of Jesus Christ that stands in 25 feet of water. It is located about six miles east-northeast of the Key Largo Cut in the John Pennekamp Coral Reef State Park. It is said to be one of the most visited underwater sites on earth!
Hawks Channel provides fantastic sailing. The barrier reef provides great protection from the ocean swells, but you still catch the breeze for some spectacular sailing. Bahia Honda, one of the best anchorages in the Florida Keys, is another one of our favorite anchorages. You can drop your hook near the historic Old Keys Trestle Railroad Bridge and enjoy the calm natural harbor at Bahia Honda State Park.
Explore The Quaint Village Of Key West
Key West has several marinas in the historic seaport or you can anchor out in Man of War Harbor or pick up a mooring in Mooring Field. It is well worth spending a day or two in Key West to take in all that this “end of the road” (end of US 1) destination has to offer. Key West is the southernmost point in the continental United States and a visit to the island almost necessitates recognizing this unique geographical fact. As noted on the southernmost mile marker, a mere 90 miles due south from that point is the island of Cuba.
Key West is rich with history, is quaint and beautiful and known for wild parties. It’s a gathering place for all kinds of humanity, some bordering on the bizarre! A stroll up and down Duval Street, Key West’s popular main party drag, boasts many art galleries, shops, bars, and restaurants and is prime people-watching territory.
Every day, two hours before the sunset, the daily Sunset Celebration on Mallory Square gets going as buskers, street performers, and craft vendors set up for crowds of people. The sunset over the ocean is breathtakingly beautiful and one of Key West’s most photographed sites. Everybody tries to catch a glimpse of the green flash from Mallory Square everyday. Check out the Mallory Square Webcam.
Marquesas Islands, A Tranquil Lagoon
The Marquesas Keys are about 25 NM from Key West and are uninhabited. A meteorite impact formed the chain of islands. It’s impact created the two-mile-wide lagoon perfectly surrounded by land. Numerous vessels have wrecked in the vicinity. Two of the most famous wrecks are the Atocha and the Santa Margarita, discovered by Mel Fisher in 1985. Apparently, it is not uncommon to see abandoned Cuban rafts on the exposed reefs!
The calm waters and nice sandy beaches provide wonderful swimming, diving, and snorkeling. The area is alive with sea life, including giant turtles, sharks, rays, and birds. Fishing is fantastic here! You literally throw the hook in and you immediately feel the nibbles on the bait. Fresh fish for dinner! So exciting! We managed to anchor about a 100 yards off the beautiful white beaches in about 10 ft of water, making it an easy swim to shore. It is also the site of spectacular sunsets. We managed to catch the green flash here on a clear evening!
Explore a 19th Century Fort On The Dry Tortugas
The Dry Tortugas is a cluster of seven islands, about 70 NM west from Key West in the Gulf of Mexico. It is a long day sail from Key West or you can also leave from from Marquesas Keys, about a 40 NM sail. It can only be reached by seaplane or by boat and is the most isolated and least-visited national park in the U.S. There is no fresh water on the island, hence being called the “Dry” Tortugas. The islands have a fascinating history with gorgeous scenery and the coral reefs surrounding the islands are teeming with colorful fish.
We anchored out in crystal clear water and went ashore on Garden Key for a tour of Fort Jefferson National Monument. Originally built in the mid 1800’s as a military fort to be used by Union forces during the Civil War, the fort was converted to a prison. Its msot famous inmate was Dr. Mudd notorious for his involvement in the assassination of Abraham Lincoln. The other islands worth a visit are Loggerhead Key, Hospital Key, and Bush Key.
We had a super time exploring the Florida Keys and we highly recommend this cruising ground to cruisers.
Florida Keys Resources
Florida Keys Information & Places Of Interest
- Florida Keys Treasures: floridakeystreasures.com/blogs/
- Florida Keys Mile Marker Guide: floridarambler.com/florida-keys-getaways/florida-keys-roadtrip-mile-marker-guide/
- Florida Keys Tourism Info: fla-keys.com
- Florida Keys Diving: scubadiving.com/
Florida Keys Sailing Itineraries
- Fun in the Sun: funinthesunyachts.com/sample-itineraries-florida-keys/
- Dream Yacht: dreamyachtcharter.com/destination/fort-lauderdale/
- Tropical Yachts: tropicalyachts.com/tours/miami-keys-ow/vacations.php
- Tula’s Endless Summer: tulasendlesssummer.com/things-to-do-while-cruising-the-florida-keys/
Anchorages and Dinghy Docks in the Florida Keys
- JFaughn Florida Keys Anchorages: jfaughn.com/crew_boat_projects/anchordinghykeys/anchordinghykeys.htm
- Waterway Florida Keys Anchorages: sailmiami.com/Intracoastal_Waterway/florida_keys_anchorages.htm
- Cruisersnet Florida Keys Anchorages: cruisersnet.net/category/all-florida-keys-anchorages/
Looking to buy a yacht? Contact us if you have any questions regarding catamarans for sale, Fractional Yacht Ownership or our Charter Management Programs.
