Sailing the Florida Keys Is a Can’t-Miss Adventure
Sailing the Florida Keys—cruising on the blue waters of Florida’s island chain—is a sailor’s tropical paradise. The only tropical paradise stateside. Have you ever caught a glimpse of that impossibly blue water from atop Seven Mile Bridge? Then you know what sort of paradise I speak of.
Tourists can reel in a glimpse of that delicious blue from the window of their car, if they can do it without crashing their car. Or they can stop at a waterfront restaurant, if there is an available table, and see the water from there. But on a sailboat, that perfect shade of blue fills the panorama. It becomes your front yard, your backyard, and every path ahead of you for miles and miles.
Once you sail into that palette of teals and turquoises, you can stop chasing the view. You are the view.
What’s So Great About Sailing the Florida Keys?
Sitting on the bow of my sailboat in Boot Key Harbor, I watch the clouds cover the harbor in foreboding shades of blue and grey. A storm rolls over the anchorage and lightning threatens to strike at a forest of conductive spires in the harbor full of hulls. Everyone huddles belowdecks, rocking and rolling for an interlude of chaos and unrest. On VHF channel 68, sailors exchange reassuring words and look out for one another as anchors drag and boats bump amidst the rolling thunder.
The entire scene changes from ominous to glorious in a matter of seconds. The winds pass and the rain slows, each drop of water transforming into a prism of golden light as the sun emerges. A rainbow covers the anchorage in a pastel platter for the sun to set on. Dolphin fins emerge and manatees make their telltale pancakes on the water.
Just like that, everything returns to normal in the Florida Keys. As I ask myself, What is so great about the Florida Keys, I look back on moments like these.
A Sailor’s Playground
The string of islands that makes up the Florida Keys is a perfect playground for sailing. A tropical necklace of coral and limestone formations creates a chain, a natural corridor of protection.
On the lee side of the western edge, the easterly trade winds and prevailing seas are buffered by the chain. Sailing along this shore offers relatively calm waters and safe anchorages amid some of the most beautiful views America can boast.
What Are the Highlights of Sailing the Florida Keys?
What aren’t the highlights, really? But we have a couple we always look forward to and talk about after we are gone.
Caribbean Illusion
The water in the Florida Keys is terrific in its shades of turquoise and blue. It’s the only place in the U.S. to experience water this blue. This is where the U.S. brushes shoulders with the Caribbean, creating a seamless illusion of the Caribbean Sea. Delicious tropical water and aquatic wildlife give us an unmistakably tropical experience.
The next closest place to find this would be Cuba or the Bahamas. But sailing to anywhere in the Caribbean from the U.S. involves a laundry list of logistical and financial planning.
The Aquatic Landscape
If your sailing goals include interactions with the aquatic world, the Florida Keys offer a unique opportunity. The marine ecosystem and geography are richly interconnected. Overall, the marine species are larger compared to most other coastal areas.
I remember sailing out of Bahia Honda on one of our excursions. I looked down beside the boat and saw a dark shape. An 8-foot-long hammerhead shark was cruising alongside us. It even tapped our hull with his bizarrely shaped head. Hammerheads aren’t quite as common as the nurse sharks or reef sharks you will see all over the Florida Keys.
And it doesn’t stop there. You will see manatees the size of small cars. Large eagle rays hover over the sea floor. And dolphins are simply everywhere in this area. On the way back from a restaurant in our dinghy, a pod of dolphins came so close I was able to reach down and touch them.
What Are the Challenges?
Hands down, the number one challenge of the Florida keys is finding a protected anchorage or harbor. Depending on your boat size, it could be even more difficult to find a slip at a marina. Like any popular sailing destination, the watery coves are peppered with other boats squeezing into tight anchorages. Many islands offer protection from only one wind direction. If the wind switches from the prevailing east, you might find it difficult to secure a protected and available spot to anchor.
Tip
Bahia Honda State Park has a few spots in its small but very protected harbor. If you are in the area and unable to find a protected anchorage, give them a call and see if you can tie to their wall. Another option is to anchor between the bridges, but expect to rock and roll all night because the current does funny things there.
What Are the Must-See Locations While Sailing the Florida Keys?
For some of the best snorkeling and diving in the area, you must visit Looe Key Sanctuary. Disclaimer: You will likely see a shark. And you might see a big one. That’s either a “heck yes” or a “heck no,” depending where you are on the shark meter.
If you have always wanted to try diving but are nervous about going too deep, this is a great place to start. The water is shallow, and the Looe Key Dive Center can introduce you to the sport. Just make sure you go when the water is clear.
The old Seven Mile Bridge is a must-see attraction. And if you are staying at Boot Key Harbor, it’s just a bike ride away. Stare down from the top of the bridge into the clear emerald water and you will see nurse sharks and rays patrolling the sea floor. At the end of the 2-mile path, the bridge leads you down to the historic Pigeon Key. Here, you can talk a little walk in history, and see the work camp of the men who built the Key West Extension of the Florida East Coast.
If you sailed the island chain of the Florida Keys and want some more adventure, your next stop is the Dry Tortugas. Crossing to the Dry Tortugas is a great way to prepare yourself for longer crossings with an easy overnight sail. The easterly trade winds make it conducive for a broad reach or beam reach from Key West.
Getting back might be another matter, unless you are planning to go all the way to Mexico. I made this sail a few years ago and found the snorkeling to be exceptional. The park is home to some of the most pristine reefs I have encountered.
Events and Boating Communities
Where are the best events and boating communities? I’ll answer that question with three words: Boot Key Harbor.
Nestled in Marathon Key, this large harbor offers 360-degree protection, which makes it a very popular destination for liveaboards and sailors waiting for a window to cross to the Bahamas. Boot Key Harbor offers a colorful swath of Floridian culture enmeshed with one of the biggest boating communities in the U.S. With over 250 moorings, Boot Key Harbor is one of the top municipal mooring fields in the country. It is unrivaled in protection and management. Learn more about the history and colorful attributes of the community here.
For liveaboard families homeschooling their children, this is a great place to drop the hook for a while. Homeschool sailing meetup groups are regularly announced on VHF channel 68. The library across the street has invaluable resources and an entire level devoted to children. You can use the address at the Boot Key Harbor Marina to apply for a temporary library card. A large building and workshop in the marina features large tables and is available for boat projects. Or use it as a place to sit and conduct some homeschooling in the shade.
The palapa, or tiki hut, is the place for parties and potlucks. Yoga classes and church groups meet there, too. Wherever your interests lie, you can find other like-minded individuals to share time with. The generosity and kindness of the sailing community is warm and exemplary at Boot Key Harbor.
What Keeps Us Coming Back
Of all of the attributes that the Florida Keys has to offer, I would say Boot Key Harbor is what keeps sailors coming back. Many sailors can exist in a transient capacity indefinitely. But for those who want to kick their feet up for a while, get some mail delivered, and make some friends, Boot Key Harbor can offer sustainability and comfort to the sport.
Olivia de Soria
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