Howling South: A No-Turning-Back Sail To The Dry Tortugas


“Yeah, I don’t even look anymore.” Bill says as he sees the look on my face.

He understands my shocked, wide-eyed expression as “Holy crap those are big waves.”

I’m at the top companionway step, looking past my brother-in-law Bill at the helm, shocked at what’s behind our boat. I couldn’t see them when I went off watch two hours earlier. Now the early morning sun highlights the white tops of huge mountains of rolling water, slowly chasing our boat down the Gulf of Mexico. I’m wondering how the hell we got here and how the hell we made it through the night.

Adventure Is Our Nickname

When you decide it’s time for a great adventure, it takes some special friends to agree to come along. Especially when your previous adventures were mostly just new and unique experiences of calamity and mishap. The plan – four guys bareboat charter a 39’ Island Packet from Port Charlotte Florida to The Dry Tortugas for seven days of sailing, drinking, snorkeling, and exploring the remote white sand beaches 70 miles from the nearest land. That’s how it was sold, and that’s how my three brothers-in-law were duped into what they thought would be an easy going, Hawaiian shirt wearing, adventure-cation.  HA!

The 90 mile drive from St. Pete to Port Charlotte is the first time all of us have been together in over a year. Jerry, the only out-of-towner, is still on Phoenix time and tired from his long flight. The rest of us, Rick, Bill and I, are passing the miles talking about the upcoming adventure. We’re discussing provisions, who packed what, how much, and “we’re really going to have a working head?” Rick is most excited about the working head. Up until now, our sailing adventures consisted of a weekend of island camping in bad weather and practicing “repairs at sea” on my old boat. This trip is far outside of our wheelhouses. As I see the sign for Port Charlotte, I’m thinking, I can’t believe we’re doing this, this is going to be incredible!

Our duffel bags of gear are piled to the roof behind the back seat, so we head to the boat first to unload, with plans to go out and hunt for groceries after the charter orientation. The marina isn’t busy and we’re able to park right next to Dock B. It’s the moment of truth. Will it be a nice boat or a scow? It doesn’t take long to find out. Halfway down the dock we stop and stare in awe at our new floating home the Patent Settlement, resting quietly in her berth. The massive 39 foot yacht looks way bigger in person than she did in the website pics. Jerry looks at me, “These people must be nuts to let us drive that – or they got great insurance!” Bill grabs a mooring line and tries to pull the boat closer to the dock. “She’s so heavy I can barely move her!”

I wonder how the sea gods will favor a boat named for a legal agreement rather than something traditionally nautical like Wet Dream. Not a fan of the name, but I love Island Packets. I holler “Let’s go get our crap guys.” as I wave them back to the car. Five dock cart trips later and all gear is aboard, and beers have been opened.

Shuttling the gear in the late October Florida sun is un-vacation like work. The guys are soaked in sweat, so we decide to take a break in the cockpit under the bimini. We’re bouncing around the idea of making Arizona Jerry’s frequent “It’s so humid!” announcements into a drinking game when a spiffy guy with a clipboard walks up to the boat. “Gentlemen, are you ready for your walk through?” “Yes Sir!” I say.  The guys have been trying to stay relatively sober to appear responsible, but we can’t hold it much longer.

His pressed khaki shorts, snappy outback style hat, and dress shirt with charter company logo make me feel under-qualified to work a fender. Captain Khaki climbs aboard and suggests we go below to start the walk through. After a few “after you’s” we’re in the cabin learning about the inner workings of the Patent Settlement. About an hour later, of which a good portion is spent reciting a list of what can and cannot be pumped through the head, Captain Khaki concludes his fecal-focused orientation with, “You know, only about five percent of the people that charter this boat do what you guys are doing. Most spend the week in the harbor, going from anchorage to anchorage.”

My eyes dart back and forth at the guys’ faces. They have a collective wide-eyed look of “How should we take that? Are we unique and adventurous – or are we doing something powerfully stupid?” After that comment, I’m thinking, “Here it comes, this is where Captain Khaki tries to talk us into changing our plans.” Instead, he says with a smile “Well, o.k., have fun and be safe. I’ll see you guys in seven days.” He quickly spins around and hops up the steps.  I suspect he’s rushing back to the office and calling the boat’s owner: “Hi, Mr. Patent Holder? I think we’re going to finally get rid of this boat for you. Is your insurance paid up?”

My favorite part of the trip to the grocery store is watching each man wheel off with his own shopping cart to get his own preferred brand of beer. In the cheese aisle, Bill pushes his cart up alongside Rick’s . “You got quite a bit there.” Bill says nodding towards Rick’s cart load of beer stacked 4 cases taller than his own. “Yeah, well I figure at least 20 beers a day for 5 days – and that’s conservative. I don’t want to run out.” Rick replies.

I’ve never seen more stress and mental calculation as these three guys trying to figure out how much beer they need to take with them. Waiting in line to pay, Bill makes one last dash to the beer aisle for two more cases. You never know, he might get really, REALLY thirsty. Ultimately, we figure it’s close to 300 cans that get stuffed in every available space down below. I’m travelling lighter with only 2 bottles of tequila and one big bottle of Sailor Jerry.

It was supposed to be a twenty-hour sail at 5-6 knots from Port Charlotte to The Dry Tortugas. I’d read it enough times in sailing magazines to remember “never come into an unknown port at night”. To arrive at Fort Jefferson in the morning, we would need to leave around noon tomorrow. Well, of course that means we can drink tonight! The four brothers-in-law together, on the first night after months of planning…my tequila stocks are taking a hit.

As the sun warms the cabin, I can barely open my eyes. This has got to be one of the top three hangovers of my lifetime. Waking up at 9:00 a.m., head pounding, holding back the heaves, this is not the way you want to feel when you’re supposed to set sail in only three hours. “We’re gonna have to cancel the trip. Call a medic. Call my Mom.” I mumbled to Rick who was standing over me. “Get up amateur. Eat some bacon.” Rick replied in a bell-ringing voice. I whined back him, “Why bacon? Why would you do that to me?” Goddam tequila.

A gallon of water and one Bloody Mary later, I’m as ready as I will be. At noon on a cloudless 80-degree late October day, The Patent Settlement eased out of her berth at Burnt Store marina and pointed west.

Godspeed, idiots.

Sailors In The Dark

The red glow of the compass is the only thing I see in the blackness in front of me. The dial suddenly spins to the east. I throw the wheel hard over, fighting the following sea, trying to keep the rudder from getting pinned to the hull. The compass dial refuses to stay where it’s supposed to be. I can’t remember the southerly heading Bill and I agreed to maintain, I can barely keep it on the damn “S”. The huge rolling waves are shoving our stern one way, throwing the boat nearly sideways, then back the other way. The relentless sound of the wind won’t let me forget how serious this is. Bleary eyed, barely able to focus, I just want to take a break. So much has changed since that point of no return moment, when we sailed out through Boca Grande pass into the lazy 3-4 foot seas of The Gulf of Mexico. Since then, this whole trip has gone in the crapper. Captain Khaki would not approve.

Before sundown, the VHF radio reported a Northwester coming through with 20 knot winds. I remembered something I’d heard from a veteran sailor: Island Packets don’t like to sail in anything less than 17 knots. “Wind shouldn’t be a problem guys, but let’s take a vote – should we keep going or go back and stay in Charlotte Harbor for the week.” All vote to press on, though later I learn almost all would rather have turned back but NOBODY wanted to be a go-backer.

Now it’s pitch dark, Rick and Jerry are seasick and out of commission. Rick has lodged himself in the rear berth and is not coming out, the “Bear’s Den” we call it. The last time I saw him was a few hours ago when he offered to go below and make us sandwiches. “Where’s those sandwiches?” Bill asks. “I’ll go check on him.” As I come down the steps, I see spread out on the galley counter: a knife, an open jar of peanut butter, 8 pieces of white bread, one with peanut butter slapped on it. That was as far as Rick got before the nausea got him.

Jerry has gotten sick at least four times and is stuck up in the cockpit. The cabin is certain doom for him. He can’t go below without puking. I holler at him over the wind, “Jerry, you have to keep drinking Gatorade, you can’t get dehydrated!” That is all I can offer. Again, something I’d read. I knew he was hydrated because all the Gatorade was making him pee, which he would go below to do. With the boat thrashing back and forth, it was impossible to stand up. Sitting room only in the head tonight sir.

After another trip to the head, Jerry crawls back up the companionway steps. Standing there in the opening with his cheeks puffed out, I can tell he is trying like hell to hold it in. Suddenly he dives to the port side, grabs the lifelines like he’s doing a chin up, and lets fly. “Jerry, get that harness clipped on – NOW!” I have never yelled at him before. This was my buddy, the guy that I hang out with, drink and laugh with.

I’m trying tough love, whatever I can do to make him clip to the safety line, but he isn’t listening. He just keeps puking. The top half of his body is hanging over the side of the boat, only his death grip on the lifeline is keeping him with us. I feel the stern rise as the boat begins to surge down the face of another huge wave. Patent Settlement rolls hard on her side as we bottom out into the trough, putting Jerry’s face nearly in the water.  “God dammit Jerry if you fall over there’s no way we’ll ever get you back on board!” I look out in the never-ending blackness imagining what it would be like to out there with only a life-jacket. Finally, he flops backwards into the cockpit with his back leaning against the cabin.

I watch him choke back whatever is left inside him as his shaking hands fumble to clip the carabiner to his harness. I keep my eye on him until he is secure. Jesus Christ, I feel so bad. This is NOT how this trip was supposed to go. Later, Jerry tells me he felt so horrible he didn’t care if he went over the side. “Look Jerry, every time you go below to pee you get sick. Just pee right here in the cockpit, I don’t care. We’ll lift our feet, it’ll run out the scuppers.” He won’t do it. I suppose he feels some sense of duty to at least use the head since he can’t help steer.

The knot meter is starting to hit 40-41, and the GPS down below clocks our boat speed at a steady 7 knots. Does that mean the wind is near 50 knots?!? Do I add the seven or subtract it? I don’t know, Jesus I can’t think anymore. “Maggie, if you can do anything to help us…please.”  Maggie, our 5th crew member, is the Grandmother of Bill and my wife. She passed away last week, and the family insisted she would have wanted us to still go on this trip. She had been very excited for us. I thought about the tiny airplane sized liquor bottle that held some of her ashes, somewhere down below in Bill’s duffel. My mother-in-law had asked that we take a bit of Maggie’s remains with us and commit them to the clear blue-green water of Fort Jefferson. “I think we’re gonna need some help to get ya there Maggie.” The knot meter drops to 36.

Two hours. That’s all we get to sleep. We had planned on four hour shifts of two men to steer through the night. Now, down to just me and Bill, two hours at the helm was all one man could take before exhaustion. Fighting the wheel with every single wave is wearing us out fast. Once below, the sound of the wine glasses crashing back and forth in the shelves behind the fold up salon table keeps us from any real sleep. “I can’t do this, I just want to sleep. Please.” I realize I’ve never been in this situation. I can’t pull over, find a hotel, or call a timeout. We’re 150 miles from shore. We would never find an inlet or harbor, if there was one, in the middle of the night in these seas. There are no options, we must keep going. Two hours gone already, my turn to steer, or more like, just fighting a big silver wheel.

“BAM!” my eyes pop open as the boom jibes over to starboard with a crash that shudders the boat. I clutch the backstay with one hand and spin the wheel like hell trying to get the boat NOT sideways to the waves. “Dammit! Thank God for that preventer!” I had only closed my eyes for a second. I felt guilty,  and bad for Bill, that must have rattled his teeth down there. I doubt he was sleeping anyhow.

Running under a double reefed main is a bitch downwind. I later learned that sailboats like to be “pulled” and running a reefed jib would have been way better. But now, we are stuck with what we have. It would be almost impossible in these waves, nearly exhausted, to change the sail configuration. I had also read a jibe at this wind speed could tear the whole rig out, and a preventer could at least absorb some of the shock. Crawling along the side of the boat in the dark, lying across the cabin head down over the leeward rub rail, tying a half-assed preventer is something I don’t want to do more than once in a lifetime.

“No more jibes, stay focused.” I’m so tired. Slapping myself on the face doesn’t help. The knot meter has calmed down a bit and reads around 32 now. What a difference a few knots can make! The wheel moves easier. Keeping the “S” centered on the compass is less of a struggle.

All the cabin lights are off and I know everyone, even Jerry, is below trying to sleep. Then why, right now, am I staring at a man and a woman, standing, face to face way out on the bow of the boat? The woman is holding a parasol on her shoulder and the man has a top hat on. They both look to be dressed in 1800’s olde timey clothing.

“WTF? Where’s Bill?”

I look down into the cabin, all’s quiet.  “How can they stand up out there on the bow? I had to crawl on my belly just to get to the mast!” I remember Slocum’s description of his Spanish Ghost captain and thinking “what a bunch of hooey”. Now, I believe anything can happen out here. A light comes on below, Bill’s getting up. THANK GOD. No way I going to tell him what I saw, or that I heard voices out in waves for the last half hour. Nope, he’ll think I’m losing it and he doesn’t need another worry right now. He’d think he was the last sane man on a ship of crazy.


Morning Revelations

“Yeah, I don’t even look anymore.” These are the first words that define the beginning of the day, after the night long struggle. The sun is up and the big, rolling waves look to be about 20-25 feet. Now, I measure waves with my own method, which is from when you’re sitting in the bottom of the trough gawking up at that goddam wall of water next to you – and add five more feet just because it’s scary as hell. At least the knot meter is holding around 29 and the sun is up. The scare factor goes waaaay down in the daylight.

This is nice sailboat (yacht), but an older one. Our navigation equipment consists of an outdated numbers-only GPS unit down by the nav table. No radar, no chartplotter, no SSB. Only the basic windspeed and depth at the helm. I guess cruising around Charlotte Harbor doesn’t require much more than a chart and pair of binoculars. Plotting little pencil marks on our chart from the GPS coordinates is the best I can do to figure out where the hell we are. From what I can tell, we are about 10 miles the hell west of The Dry Tortugas. I yell up to Bill “You gotta put the compass on 120 and hold it there or we’re gonna miss the fort! I’ll fire up the motor so you have more control!” Knowing the new course will put us nearly broadside to the big rolling waves, Bill says to himself, “Allright F**K it, let’s do it!” and puts the wheel over to port.

Thank God we got here after the sun came up. Even going 7 knots, faster than I had planned, it was already 8 a.m. and we have yet to see the fort. Bill is at the helm now and spots one of the outer buoys. By sticking to the dark water, we find our way to the channel leading to Fort Jefferson, a squat brown snickers bar looking shape on the horizon. Less grand than I had imagined. “Calm water dead ahead!” I holler out with much relief.

The crew’s collective sphincter unclenches as soon as we get behind the protection of the reef. The channel heads north; facing into the gale for the first time in 20 hours, my hat is ripped off my head. Bill and I look at each other “Don’t even think about it!” I holler at him over the howling wind as I watch my favorite hat vanish in our wake. It’s a fun policy back on my boat in St. Pete to treat any lost hat as man overboard practice. It gives us something to do when putzing around the calm intracoastal. Today, the hat drowns.

Now that we’re pointing into the wind in calm water, I decide to drop the main. I lash it down the best I can by myself. What an ugly, unsailory mess. Thank goodness we have other propulsion – all hail the diesel motor!

Down in the cockpit, I’m looking at the chart while trying to keep the wind from tearing it from my hands when Bill taps me on the shoulder. With that funny Bill smirk, staring straight ahead, he motions with his thumb for me to look over his shoulder. The empty 12 foot inflatable dinghy we’ve been towing all this time is completely airborne, flapping around at the end of the line cleated to our transom. It takes a couple guys to lift and manage that dinghy, and it’s trailing through the air like a kite without a tail behind us. Unbelievable.

I’m just going to say there’s never, in the history of sailing, been a group of idiots as relieved as us to drop anchor in the green water of Garden Key. Rick emerges from the Bear’s Den, hair matted, eyes wide. Jerry is down in the cabin, rummaging for something to eat, while Bill and I discuss how he also saw apparitions during the night – a figure standing right in front of the helm station. With the boat anchored and secure at 10 a.m., all hands decide it’s time to go below for some much needed sleep.

Five hours of sleep later, we’re still feeling like punch-drunk zombies. We fire up the motor for hot water from the heat exchanger – showers all around! They’re hasty, don’t-use-too-much-water showers, but still the best showers we’ll ever take. Rick and Jerry whip up an amazing steak and broccoli dinner as a thanks for not letting them die on vacation. As we eat, we take turns describing how each of us had planned to get to/swim to the EPIRB when the boat inevitably went down. Generally, all the plans were the same: grab EPIRB, extract Rick from Bear’s Den, deploy life raft. A few plans varied with grabbing wallets, phones, or the rum.

There’s no better reward in the world for four guys that managed to sail 130 nautical miles while riding a near gale down the Gulf of Mexico than kickin’ back safely at anchor. The ordeal that became a hell of an adventure is something we still talk about whenever we get together. Bill says it’s the most fun he’s ever had. Rick calls it “scared sober” because he drank less than half of his beer, and Jerry keeps asking when we’re going to do it again.

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