One of the truly great cruising destinations on the planet is just a daysail away from South Florida: The Bahamas. Much has been written, blogged, and vlogged about this boater’s paradise, and for good reason. However it can be tricky to get to with the Gulf Stream to cross and weather windows to wait for. If you find yourself waiting for weather near Miami or perhaps coming down the West Coast of the Florida, I’d encourage you to take a detour down to another great archipelago: The Florida Keys.
About a year ago my family and I set off in our sailboat from Clearwater, FL. After a few weeks we found ourselves smack in the middle of the Keys, in the very cruiser friendly haven of Boot Key Harbor in Marathon. This was a homecoming of sorts, as my wife and I had lived in Key Largo for six wonderful years where I first got started in the yacht brokerage business and earned my Captain’s license. So it was with excitement and a healthy dose of nostalgia, that we were able to revisit some of our favorite cruising and shore-based destinations and show our daughter this special place.
The Keys stretch North to South from just off Miami down to Key West (and further). They are bordered on the Atlantic side by the third largest barrier reef system in the world, and on the Gulf side by Florida Bay with thousands of small mangrove islands. You can get back and forth from one side of the islands to the other via several 65’ bridges, and one draw bridge at Snake Creek. Catamarans are uniquely suited to explore this area as the Bay side can be quite shallow.
When heading South from the Miami area, you’ll first have to decide if you want to go on the Atlantic side down the Hawk Channel, or stick to the ICW through Biscayne Bay and bays further South. This choice will largely come down to your mast clearance, as there is a 65’ bridge near Key Largo, over Jewfish Creek. Coming down the Hawk Channel, your first stop will likely be around Key Largo, doable in a long day from Miami. There are several marinas, a mooring field overseen by Pennekamp State Park, and anchorages near Rodriguez and Tavernier Keys (though best used in settled weather).
On the Bay side, there are several anchorage options in Blackwater Sound, Tarpon Basin are just two; there are too many to mention here and it is well sheltered from the prevailing Easterly winds.
One of our favorite anchorages on the Bay side is found behind lower Matecumbe Key, just to the South of Islamorada, in Matecumbe Bight. This is a well protected spot with good holding and lots to see on the dinghy; from a small sandbar, to beautiful waterfront homes, and a cool mangrove tunnel that the local fishermen use to access this area from around Robbie’s (where you can feed giant Tarpon at the docks).
There are many restaurants along the way with day docks for dinghies too. The wildlife and fishing are also fantastic on the bay side. Expect to see Osprey, Bald Eagles, Roseate Spoonbills, Herons, Pelicans, Dolphins and more back here. Many of the reef fish start their lives here around small mangrove islands, and it can be a cool opportunity to snorkel some of these roots. I have seen lobster, Tarpon, Snook, snappers, and even tiny tropical fish like Sargeant Majors around the mangroves.
On the ocean side, there are fewer and further between anchorages. A nice spot to visit on the ocean side is the State Park at Indian Key, only accessible by boat. Here you’ll find the ruins of what was a thriving settlement in the early 1800s. The town rivaled Key West as a prosperous port fueled by the industry around salvaging shipwrecks on the reef. History buffs will rejoice at digging into the unique stories found here, and it’s also a beautiful spot with wildlife and several trails crisscrossing the island, that follow the original grid of the settlement.
Continuing down the island chain, most cruisers will spend some time at Boot Key Harbor in Marathon. The city run marina and mooring field is very cruiser friendly with shower facilities, workshop areas, social hours, music nights, dinghy drifts, and pump out vessels.
There are many local attractions that are fun to check out as well: The Sea Turtle Hospital and Pigeon Key tours are both well worth your time. The moorings are affordable, well protected, and numerous! In peak season there can be a waitlist, but often you can get a ball quickly and stay as long as you like. If this is as far South as you plan to go by boat, you can rent a car or hop a bus down to Key West and spend a day visiting there.
Boot Key is a great turnaround spot as well, because by now you’ve probably spotted a weather window to allow you to cross the Gulf Stream for The Bahamas. Luckily from here you can leave direct or take a daysail back to Key Largo and stage yourself at Rodriguez Key. By leaving further South, you get the push from the Gulf Stream as you cross to Bimini or points beyond.
I hope that you’ll find some time to visit the Florida Keys by boat and unlock some of the potential of this often overshadowed cruising grounds.
Questions on sailing this area, looking for more catamaran tips on these cruising grounds, please feel free to contact Bill Regan directly:
