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Keys Part 3 - Clearwater -> Boca Grande.

Departure Date: April 18, 2025

Arrival Date: April 19, 2025

Distance: 96 Nautical Miles

Time: 28 hours

Departure Time: 13:40

Arrival Time: 17:43

Hours Motored: 6

Fish Caught: 7

Redfish - 1

Speckled Trout - 1

White Trout - 3

Jack Caravel - 1

Bull Shark - 1



Sailing out of Clearwater felt electric. The kind of excitement that lives in your chest and surges with every gust of wind. The forecast promised fair winds and two-foot seas—perfect sailing conditions. Quark launched into the open water, averaging a smooth 4.5 knots with a steady 15-20 mph broad reach. I was able to trim the sails just right, and she rode effortlessly without needing to reef down.



As the sun began to dip below the horizon, the sky lit up in a watercolor wash of orange and pink, and suddenly we weren’t sailing alone. A few curious birds started circling Quark—then more. Before long, I had three tiny stowaways hopping around _inside_ the cabin! One even perched on Belle for a while, and another nestled on my foot like I was just another piece of deck furniture. The fishing line was out, but the ocean wasn’t biting.


Right after sunset, the wind died down, and I decided to experiment with the spinnaker—just for fun. The experiment was short-lived, as the wind shifted and had me pinched off. Rather than fight it, I eased off course and sailed farther offshore. The waves grew, but with long 8-second intervals, it was like riding nature’s own rhythm.




That night was unforgettable. Swells reached four feet, and I spent hours standing in the companionway, grinning like a fool, feeling like I was surfing a giant board through the Gulf. The wind sang through the rigging in a new way, creating ghostly tunes that made me feel like Quark had a voice of her own—or that someone else was whispering on board. Eerie and beautiful.


Just after sunrise, I got a message from Footloose. Not the kind of message you want to receive offshore: he’d broken a section of his standing rigging during the night. He had stabilized the mast using his topping lift and was under motor power, but he was low on fuel—Clearwater hadn’t had any diesel available. He made it into Venice Beach to refuel while I continued south toward Boca Grande, where we planned to reunite.




On the way, I hooked a mahi-mahi—only to lose it right at the boat. Under normal circumstances, I would’ve been bummed. But with everything going on with Footloose, it didn’t even register as a loss.


Approaching Boca Grande Pass turned into an unexpected challenge. The current was flowing out against me, the swell was stacking up, and—like a minefield—fishing boats were parked across the entire pass. It’s a popular fishing spot, sure, but the behavior of some of the captains was downright reckless. One young guy in a $200K boat even started trolling right across my bow, dropping a line directly in front of Quark. His lure passed under my hull on one side while the line dragged on the other. I asked him to reel it in. His response? Cursing and a middle finger.


I carry a knife for a reason. I cut the line before it had a chance to foul my prop. The guy wasn’t happy, but thankfully an older man on board gave him a verbal slap on the back of the head and apologized on his behalf. I carried on, cutting through the rough pass, and eventually dropped anchor near Footloose at Punta Blanca Island.




The next few days at Punta Blanca were peaceful—a welcome change. We researched rigging fixes for Footloose_ did some fishing, explored the area, and let ourselves soak in the stillness. Easter night was one for the books. We grilled fresh redfish and served it with brown rice, mushrooms, tomatoes, sautĆ©ed green beans, and a homemade sauce I whipped up using pepper jelly, soy sauce, and juice from a mandarin orange. It was better than anything we could’ve found in a restaurant.



The following morning, Footloose pulled anchor and motored to Fort Myers’ Pink Shell Marina and Resort. He took an Uber into town and managed to get the parts for a temporary rigging fix. I sailed solo to nearby York Island—a protected manatee area—and dropped the hook there for the night. When the sun rose the next morning, I made my way to Fort Myers to meet back up with _Footloose_.


We both refueled at Moss Marina and set our sights on the Dry Tortugas. Quark was back to sailing, while _Footloose_, still restricted to motoring, kept pace his Volvo Penta engine.


Next stop: adventure in the Dry Tortugas.



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selfie of myself coming through Pensacola's 3 Mile bridge

About The Captain

You'll often find me aboard my sailing vessel, Quark, with my dog, Anabelle, exploring the Gulf Coast. Together, we share our firsthand experiences and the best of what the beautiful Gulf Coast has to offer.

© 2024 by The Gulf Coast Sailor. All Rights Reserved.

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