Boot Key Harbor

We have arrived! From the day that we came into possession of our first boat, the Frog, our vision was to get her (or some other lucky girl) south to clear water.

7 years ago we took a trip to the Florida Keys by car, and stayed at a cheap-as-hell air b and b in Boot Key Harbor…. on a sail boat. 

The boat we stayed on during our trip would actually run aground every day at low tide, and bump into the boat closest to us that was on a legitimate mooring ball. Whoever owned this boat had stuck it in the mooring field on an anchor in shallow water, and made themselves a killing at the expense of unsuspecting air b and b tourists looking for a deal. The “taxi” to the boat was a drunk guy with a joint in his hand and Gollum tattooed on his leg. This was a one way taxi to our little motel room on the water. He did not seem intent on coming back to take us to shore if we so desired. And even if he did, I wasn’t going to trust my luggage in his dinghy more than once. I remember seeing the pitiful look on the faces of some unlucky tourists being deposited onto another derelict boat not far. They had a white knuckle grip on their rolling suitcases as they contemplated the future of their vacation on a broken boat at anchor with no way to get to shore.

Lucky for us, we came equipped with a kayak and a sense of adventure. We spent the next few days meandering around sister creek, swimming with manatees, catching bonefish and snappers, and exploring the mangrove tunnels.

As grungy and disgusting as that little boat was, Boot Key Harbor intrigued me.

2 kids and 2 boats later, here we are. 

Needless to say, this little boat haven has undergone quite the makeover. They definitely don’t allow air b and b on boats here anymore, and the mooring field is a lot cleaner. They actually have pump out boats that will come to your boat for free so you don’t litter the harbor with poo.

Bruce Popham is the man to thank for that. He convinced the city to pull something like 200 wrecks from the harbor. The harbor has undergone a lovely transformation from a boat graveyard to the best managed municipal mooring field in Florida, and home to possibly the biggest organized social boating community in the U.S. Bruce deserves a metal, or at least a hug from all the cruisers in the harbor.

There’s a cruisers net daily on channel 80A, with a myriad of organized events/announcements/greetings pretty much every day for cruisers and their kids.

Boot Key Harbor is an incredibly protected body of water making it a popular stop for boats headed to or from Isla Mujeres and the Bahamas and other clear water destinations. It’s perfection if you’re on a mooring ball. And if you’re not, you’re at anchor packed in like a sardine waiting for your turn to get a ball. The waitlist for the 250 some mooring balls starts accumulating pretty much at the start of cruising season. The holding here isn’t great, and the waitlist is enormous, and the space is limited. Those are all the ingredients necessary for some anchor dragging and boat bumping.

I was lucky enough to witness some of the chaos while we were at anchor, waiting for a ball.

Such a quick roundup of rescue dinghies! One boat bumped another boat and in a blink there were at least 5 dinghies on the scene to hold off the intruder. They pushed the boat off and held it off until the owner returned.

 I guess this happens a lot here. 

While today Boot Key Harbor looks like a neatly arranged and tightly packed parking lot for boats, it was most likely one of many protected hideaways for pirates lying in wait.

The Florida keys are adorned in pirate lore from head to toe. The true accounts are a lot harder to track down. The keys did not have a commercial harbor like the Bahamas, which overflow with real documented pirate mischief. But we do know that the protected creeks and coves in the waters here were a haven for pirates who brought their booty back from pillaged ships in the Gulf Stream.

“Black Caesar” is one of the more popular pirate tales bantered about in the Keys. This “larger than life” African chieftain held his pirate lair in Elliot Key. He and his partner would approach merchant vessels posing as shipwrecked sailors in a long boat. Once close enough to the vessel, they would rob their would be rescuers with a pair of pistols. Black Caesar’s story begins on the African Coast, where for years he evaded captivity by slavers with clever cunning. After losing their prize time and time again, the slavers changed their tactic and lured the chieftain with colorful scarves, jewelry, ticking watches, and other things of the ‘treasure’ variety. While he was temporarily blinded by the promise of shiny gold and colorful troves, the slavers slipped off their mooring before the chieftain could look away from the gold. Black Ceasar was chained up in the belly of a boat filled with human cargo headed for the West Indies. After what must have been a grueling and horror filled journey, a hurricane broke the boat apart outside the Florida Keys. Our larger-than-life free man washed ashore on the northern coral beds of Florida. He was not alone, there was one other surviving white sailor who actually helped him escape his chains during the storm. Piracy became their future until a quarrel over a woman… Black Caesar killed the sailor in a duel and eventually took up with Black Beard. His tale ends at the noose, where many pirate stories end. If they weren’t caught, they probably weren’t accounted for.

Even more interesting to me is the ‘wrecking’ history of the Florida Keys. Any non-farming settler in the Florida Keys took up the wrecking trade. Not at all like the raping and pillaging sort of our pirate friends above, the wreckers of the keys were out to salvage the goods that came off the countless ships who met their end on the treacherous Florida reefs. They were like an early coast guard, rushing to find survivors before salvaging the ships stores. In 1828, a legislation passed requiring salvage from wrecks in U.S. waters to be brought to an American port of entry. That congressional move made Key West the wealthiest city per capita.


Does that mean Key West was built on the backs of treasure hunters? it shows! Nothing glitters quite like Key West in the moonlight. So much sparkle. There was also some lime farming, and pineapple trading, and cuban cigar factories in the mix there. And shark hunting for leather! 

Getting here was the best part of our journey. The water opened up to clarity and lovely shades of blue and green. 

We went through a flight of cormorants that never ended.

From Miami we entered the Biscayne bay. Big blue water with open ocean to the east. Miami’s horizon gave us a long farewell as it lingered in the distance for miles and miles. We sailed (actually sailed) to No Name Harbor. (Did you forget this is a sailing blog? I almost did!)

It was just a few miles from marine stadium, but we wanted to save the bay for good weather so we waited out some wind in the harbor, in the tightest anchorage we had seen yet. We were so excited to get the last spot in the anchorage, until, unbelievably, at least 20 other boats managed to come in and anchor after us. No name harbour is a tiny little cove full of sailors waiting to go to the Bahamas, and motorboats partying like it’s a weekend in Miami.

We are finally in the keys! Jeeze it only took a month. 

The next day we sailed to Boca Chita. Which it turns out is technically the key right before the first Florida key.

Okay now we finally made it. And the scenery was like a welcome sign. A tiny key with beaches full of the prettiest little sea shells I’ve ever seen.

Manatees hung out in the harbor all day. The water was pristine and blue and just gorgeous. The key was so small it felt almost intimidating in a mysterious and adventurous sort of way. The island feng shui was just right for a light house murder mystery or something.

Emilia was playing with ‘mermaid foam’ on the beach when I noticed something purple on the shore. This little purple balloon was a man-o-war. And he had a friend! 

The Nomeus gronovii (also known as man-of-war-fish or bluebottle fish) lives unharmed amidst the stinging tentacles of the famed jellyfish.

We left the lovely confines of Boca Chita and headed to Tarpon Basin off Key Largo. Very protected with good holding but brown muddy water. No dinghy docks here, as the park which usually has open access from the water, is closed. We called every shop on the water in the Basin asking for dinghy dock access, even throwing “but we just want to get our kids to shore” in the mix there, with no luck. We lost all hope and called the Hampton inn right in front of our anchorage, and to our amazement they let us use their beach! So we kicked it there a few days. We went to a restaurant called “Restaurant and Bar” which cracked me up. Best Caribbean food I think I’ve ever had. Makes my mouth water just thinking about it. They put some coconut magic on their fish and a little carribean spice and had a party in my mouth.

On the way back from the best dinner ever we saw an ROUS (rodent of unusual size) running to the dumpster behind the Hampton inn. 

Im hoping it was a cat. But hey, we are in the keys now.

We headed to Pidgeon Key a few miles south where the sunset made a debut.

The water near pigeon key on the windward side was like an aquarium. Adam paddled back and forth just taking in the aquatic life. And unsuccessfully hunting for lobsters. We are a little late in the season I guess. But someday we hope to put this ‘lobster tickler’ to good use.

We tried to fuel up at a marina in Cowpens Anchorage. Bad idea. It was a quarter mile of skinny maneuvering to the fuel dock at the very end of the stretch. There was already a huge boat fueling up so we had to ‘hold still’ and wait since there was no where to go from there. When the boat at the fuel dock finally took off, an oncoming drunken motor-boater tried to push past him, forcing him to back up right into our bow, pushing us into the mangroves behind us. Road rage is one thing, water-rage is a whole nother beast that can surface in moments like these. I fumed and yelled and pointed and… well, when it comes down to it, there just isn’t anything you can do. A big boat that maxes out at 7 knots is like a slug crossing the sidewalk in the sun. You just hope you can make it.

Our anchorage outside the marina at Cowpens was crystal clear to a grassy bottom

That night, we had fun with some more anchor dragging.

That feeling! When you wake up and look at your navionics ‘route’ and instead of a tight little crisanthimum bundle of yellow lines, you see the dreaded straight line shooting out of the fold, leading to god knows where in the middle of the night. 

It feels like a screaming new born with insatiable needs when all you want to do is sleep like the dead. 

The wind howled while Adam and I bickered about how to solve this problem, and who was to blame for not preventing it. Anchor drama dammit! Gets us every time. In the end we just let out a bunch more chain and didn’t really sleep at all till morning.

Im wondering if a Mantis might be a solution to all this. We have a Manson Supreme, which is good in that its a next generation anchor.. But everything I’ve heard about a Mantis seems to equivocate a good nights sleep. 

The next day we headed out snakes creek bridge for some snorkel magic at Hen and Chickens. Just a few miles in the ocean and it was a bumpy ride.

The month and a half of windy weather here in Florida has really been kicking up some sand. Hoping for some clear days of snorkeling soon, but not holding my breath. Some say this is normal, but most say this has been a cold and windy ass winter, much worse than average.

Next stop: 

Boot Key Harbor! 

Our anchorage was probably 1/2 mile from the dinghy dock, and each ride through the harbor was worth every second of the trip down here.

And the 7 years really that it has taken us to get here.

When you drive through an RV park, the rvs don’t really add to the view. But when you dinghy through the million dollar boat show here, the towering masts in front of a watery sunset really do put their own stamp on the scenery. 

I guess for some its probably a drag being here, packed in like sardines with boats literally everywhere you look. Even as we speak I can hear a couple bickering on a boat nearby. You definitely can’t hide any dirty laundry out here! All your colors (lights and darks) will fly free as the wind. 

After witnessing the boat dragging drama, we were very happy to get the call that we came up on the waitlist. 

Arriving a little late in the season as we did, it only took us a week to get a mooring ball. We just hooked up to it yesterday! It wasn’t until after we got on the ball that I realized after each gust of wind would hit, I would wait and feel if the anchor would catch before letting out a breath. Last night, I slept beautifully.

Next stop? I don’t know. Might just kick it here for a while and enjoy the view, and be the view.

13 responses to “Boot Key Harbor”

  1. Such a good read! I love your posts, it’s been so fun following along. You are a very talented writer; I really look forward to these great stories about your adventures. Your words create so much color and vividness to the minds eye.

    (Remember we met over tacos in Hot Springs)

    1. Hi Elicia! You and your family were very inspiring to us that day we met. The time is coming for us to decide about whether or not to homeschool. Such a big decision! All the info you shared with me is very helpful in making that choice! It was a serendipitous day when we met you!
      Thanks for reading our adventures

  2. CONGRATULATIONS Y’ALL!!!! Sounds very busy place compared to Oriental, NC?

    1. Yes it is quite a bit different than oriental. Although I already miss the shrimp boats at the public docks and the greasy food at m and ms.
      I hope you’re enjoying some lovely sailing in the Netherlands!
      Thanks for taking the time to read

  3. Another fine boatnote from life aboard. Love it. Thank you!

    1. Thanks Barney! See you at the lake!

  4. I always enjoy your saga. So glad I had a part in it. If my B&B guests provided me a means of traveling the world through their tales, you and Adam have satisfied my yearn to travel by sail. Thanks. Love you all

    1. We miss seeing you Chris! So glad we had a chance to spend that time with you at your B and B. I hope you are doing well!
      ❤️still hoping to stop by Richmond on our way to DC area and visit you

      1. Just reading this, almost one year later. Please visit when you can. My new lady friend and I have 2 condos with spare rooms to possibly accommodate you. We live our dreams thru you!!!
        Love Chris and Ann

  5. I’m so happy for y’all. Love all the pretty water. And really liked the videos of the dinghies acting like tugboats and Adam trying to pick up the mooring ball. I also think those very dangerous men of war are an absolutely perfect color.

    Looks like you’ve found your spot!


    1. Thank you Lee!! I’m so glad you are following along! I hope you had a good time in Florida, it’s been crazy weather.
      Can’t wait to see you guys this spring/summer!

  6. You are an amazing writer and I just Love reading your travel stories! Continued well wishes to your sweet family from the little boutique, Wildflower & Whiskey, in Georgetown, SC!!

    1. Thanks Jill! I love that you are following along! We finally ditched the sweaters and I get to wear that lovely dress from your shop.

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