Notes from the crossing: Anclote to Captiva


When we left the mouth of the Anclote River there was a stiff north wind blowing 15-20 knots. It was 1100. Emily steered us through the narrow channel that leads through the grass flats on the east side of the bay as I hoisted the jib and mainsail. Once the sails were made I came back to take the tiller.

Emily and I made a deal on this crossing. She wasn’t feeling well, and I didn’t want to sit at our anchorage another day, so I decided to do all the work. I would sail the entire passage from Anclote to Marathon or Marco Island — or wherever I got too tired and needed to duck into a harbor to rest.

I fervently watched the Anclote Key lighthouse rush by us as we sailed out the pass. I have an emotional response to lighthouses now that I’ve stood watch, waiting and hoping to spot a light on the approaching, unseen shore. Searching for some indication that we were close to safety. And here we were once again, saying goodbye to the safety of land.

The waves picked up to 2-3 feet once we got out of the lee of the island, and we felt the full force of the north breeze. We were cruising at 6.5 knots with our full genoa up and a single reef in the main. The waves started rolling us on our broad reach. Emily held the tiller for a moment while I set up a sheet-to-tiller steering system.

The broad reach is really finicky when it comes to sheet-to-tiller self steering systems, but I’m getting a pretty good feel for what our boat wants. I got it rigged and the boat immediately turned downwind. As intended, she immediately corrected herself — the mainsail started to block the genoa, the sheet tied to the clew of the genoa went slack, and the bungee on the opposing side of the tiller tugged on the boat — and in just moments, she softly rounded back up, bringing us back on track. She scooped out gentle slow S-curves, nosing fully downwind and coming up, nosing downwind and coming up. I set it right on the first try. Nice.

Emily went to sleep under the shade of our new dodger, nestled into one of our new beanbags. I sat on the other beanbag, up on the stern behind the mainsheet. I watched our little boat sail itself on a broad reach for two hours as we cruised southwest along the coast, slowly leaving Clearwater and St. Petersburg behind us. It was mesmerizing to watch her turn and surf down the waves. Just as she would threaten to broach, the self-steering system would tug her at the crest, setting us up perfectly to surf the next wave. More than ever before, I felt like her caretaker. As long as I did my job right, setting her up and maintaining her correctly, she would do all the work: sailing us wherever the wind could take us.

We lost sight of land six hours into our passage. As the last pink buildings on the beach disappeared over the horizon and the water started turning a deep blue, I saw two flying fish pop out of a wave and soar through the air. The way they moved was unnatural. Any fish I have ever seen would have dropped into the back of the next wave, but this one flapped its fins and and hovered itself off over the horizon.

Thirty minutes later I spotted a sea turtle about fifty yards away. It must have been six feet long. It poked its head up then dove back down. I woke up Emily. “Sea turtle!” “Where?” She asked sleepily. “Over there! It’s gone now though.” “Oh…” she said. She said her head was pounding and went below to rest. I started to regret taking us out when she was feeling under the weather, but she seemed happy just to be on the boat as long as I didn’t need much from her.

I was happy taking care of the boat myself. Since we started this trip, I had wondered what it would feel like to single-hand the boat on a passage. I’d heard about people sailing Cape Dory 25s around the world by themselves. This was my chance to see what it feels like, at least for a little while. Just before sunset I enlisted Emily’s help swapping the genoa for the working jib and setting the second reef point. Then she went back to sleep. From that point on I let Emily rest as much as she wanted. I was on my own with the boat and I felt good.

We jibed around and started to head back towards land. The wind was forecast to shift to the east later that evening and we wanted to be a couple of miles offshore when it shifted. Then we’d be able to run on a beam reach through the night. I heated up some chicken noodle soup and watched the sunset. It’s amazing how much more pleasant it is to sail when the air is 60 degrees — it was 40 on our last passage. I was also pleased that I was comfortable enough on the boat to operate the stove and hang out below deck while it was rolling without getting too sick.

As night set and we grew closer to the Tampa shipping channel, I started to get nervous. I was on high alert looking for ships that might cross in front of us when we got into the channel. Far off on the horizon was a ship that seemed too far away to worry about, but I monitored its motion carefully. As we crossed the channel safely, I saw a massive container ship leaving Tampa. I watched it heading out into the Gulf as we sailed on our merry way. Well, there’s no missing that ship out there, I thought to myself. It looked like a house decked out with Christmas lights. I could see it miles and miles away over the next couple of hours until we each sailed over our respective horizons.

When we were 3 miles offshore, just south of Egmont Key, the wind shifted to east and picked up to 20 knots. I set up the sheet-to-tiller steering system for our beam reach and marveled at our speed. We were clipping along at 5.5 knots. I had to let the mainsail luff considerably in order to get the self steering system to cooperate, and it seemed unhappy at times, banging away in the hard wind. I hope to God I’m not hurting this sail, I thought. I allowed myself to relax on the beanbag, watching the stars, as the pounding of the sails and the waves crashing over the bow receded into the background of my consciousness. At midnight I had been on watch for 14 hours and I was getting tired. The beating of the sails and waves crashing over the side of the boat was starting to take its toll on my psyche. I trimmed the sails properly and hand steered for a little while. We picked up speed, cruising at 6.5 knots, but the waves started to really crash over the bow.

At 0100 Emily emerged from below deck. She seemed refreshed. “Whoa, we’re really getting pounded, aren’t we,” she said. She went back below and turned on the cabin light. She lifted the bilge cover and hollered, “we’ve taken on a lot of water!” The bilge was 3/4 full. A lot more than we’d like. She started the bilge pump and we started wondering why we were taking on so much water. We decided to heave to and check out the seals we had installed on the lazarette hatches. We’d taken on water that way before, and we suspected them again. Sure enough, the lazarette seals had come unglued. Waves had been pouring into the cockpit, draining through the seat hatches into the lazarettes, and dumping into our small bilge. I made the command decision to stay hove-to for a couple of hours so that I could rest without Emily having to take a watch in such difficult conditions.

I sat for a moment and watched the boat, hove-to in 20 knots of wind, with our main reefed at the second point and our full working jib up, waiting to see any sign that she might come about and send us on a wild ride. But she seemed happy, hove-to, drifting sideways at 1.5 knots. Emily took one of the bunks and I took the vee-birth. The boat was heeling about 20 degrees, so we were both nestled hard against the inside of the downwind hull.

The sounds of our boat moving through the water while being hove-to were bizarre. From time to time, we would hear a massive plowing sound from the bow, as though the boat were pitch polling into a wave and water were rushing up over the bow. When I first heard it, I hopped out of the bunk and went on deck to see what was going on — and the boat seemed fine, just as I’d left it, gently letting the two- to three-foot seas roll beneath. I decided that I would just have to let the boat make noises as she pleased until I heard the sails start to luff. Then I would know we were no longer hove-to. I lay in bed and tried to sleep, imagining that every toss and shift of the boat was her bearing off the wind and starting to run on her own. It was a strange feeling. I was able to get a little rest.

At 0500, I got up and decided to get the boat running again. It hurt to let too much of that good wind go to waste. Just as easy as we’d hove to we were back at it, plowing through the waves at 5.5 knots. Besides the little sideways jag on our GPS track, it was as if the Gulf had waited while I slept, right where we’d left off.

Emily got up at 0700 and watched the sunrise with me, then offered to take watch so that I could get some sleep. I went below and slept for two hours. When I got up, we hand bailed the bilge, which luckily hadn’t taken on too much more water. The seas started to settle a little and the wind started to let up. It felt like such a gift to have the stiff wind relax enough for us to sit in the cockpit without getting a wave in the face. But no sooner had morale begun to lift than the wind died out from under us. Damn! We had only fifteen minutes in perfect conditions — seas 1-2 feet and an easy 10 knots of wind. But it just couldn’t last. I’ve given up on hoping that the conditions will improve. Usually you end up getting what you asked for and it’s not what you wanted. I’d rather have 20 knots and be uncomfortable than be sitting in near glassy conditions with no wind.

On the other hand, no wind means that jumping off the boat and swimming in the incredible 60 foot deep water is an option. I jubilantly leapt off the top of our new dodger. With a mask and snorkel, I dove down to inspect the boat in the crystal clear water. The full keel is beautiful from underneath, encapsulated by the blue-green of the Gulf, haloed in the light of the sun shining above. I almost got vertigo looking down into the clear deep blue. My interest in free diving was further piqued. How long would I have to hold my breath to dive to sixty feet without air?

Emily and I have loved working on this boat, and our adventures so far have been fantastic life experiences. We started sailing in the waterways of North Florida — the Florida I love because it’s where I grew up. Where dark tanic waters of the deep water bayous wait under live oaks. Now it feels like we’ve entered a new realm — one of crystal clear waters and coconut trees. I’m researching breathing techniques for free diving while Emily reads up on remote keys that we want to explore around the Dry Tortugas. Spirits are high on the Hard A Lee.

Carrabelle to Clearwater, FL

13 March 2018
06:00 EDT
29.850480, -84.667534
Two hours before sunrise.


For about an hour, the boat had been gradually tilting to port. Haden was comfortably curling deeper into his corner of the vee-berth, but I was increasingly at risk of rolling on top of him. When the tilt grew too acute to be a part of a dream, I roused myself in the dark and asked Haden, “did you leave the jerrycans hanging from the boom?”

The day before, Haden had tackled the leaking bilge output, for which he’d had to heel the boat to port. He swung out jerrycans full of water on the boom to hold the boat askew while the spucky dried. But he had disassembled that before nightfall, and mumbled “no,” so I got dressed to investigate. The moon was rising in a thin crescent and the air was cold and wet. In all my layers, I shivered as I climbed out the companionway to stand on deck and look around. I realized suddenly that the normal rocking of the boat was absent. We had run aground.

We were anchored in the Carrabelle River, where we had spent the past week and a half waiting out the weather, which at this time of year consists of cold fronts sweeping through in week-long rotations. We were aiming southwest, hoping to get as far as Clearwater on our next leg, and we knew that to make that 24-48 hour trip in the middle of a cold front would be not just uncomfortable, but dangerous. We needed to prepare the boat for blue water sailing, so there was a plethora of projects to do while we waited. Really, the best reason to stick around was our friend Greg, who lived and worked at the nearby boatyard. Greg has been blue water sailing with his wife Bonnie since 2006 in a boat he spent three years building himself. We had a lot to learn from Greg, and spent a lot of time making sure we could follow his advice on our outgoing trip. We installed netting for every shelf, constructed a new tiller, sealed the bilge, learned to heave to, built self steering systems, and kept an eye always on the weather. We decided to sail out between cold fronts, a trick the commercial fishermen use. Between late winter fronts, there’s usually a two day window of 15-25 knot winds out of the north and west, which is a little strong for comfort but effectively perfect to get us across the gulf.

This was our planned day of departure, and we wanted to be out by sunrise. But we are but mice and men, and nature enjoys playing mischievous games with our plans. During the night, the strong northwest wind had pushed us away from our two anchors into shallower water. This coincided with the lowest tide we had had all month, and we were hard aground. The water would only continue to drop for the next hour, so we needed to rock the boat off now or be forced to wait for the tide to rise in the late morning. I woke Haden up and we got to work.

First, we tied off the five-gallon water and gasoline jerrycans to the boom and swung it out. Haden filled every bucket on the boat with water or chain and set them on the port side. If we could tilt the boat far enough to port, she might slide off. We rocked back and forth on the boom, pulled on the mast, begged, pleaded, and prayed, but an hour and a half passed and the sun rose on the Hard A Lee pressed deep into the river muck. Exhausted and cold, we found there was nothing to do but to go below and sleep until the tide rose enough to help us off and away.

By 10:00 it had, and we were finally able to rock ourselves free. We nearly ran aground again trying to retrieve our second anchor, but the tide was on our side now and we made it at last out the river mouth. We raised the sails in a beautiful 10 knot breeze and exuberantly headed for the pass. Haden set up our sheet-to-tiller steering system, which with only a minimum of attention took us right out the pass between Dog Island and St George Island. The weather was perfect and we were filled with confidence, excitement, and wonder. The wind died for a couple of hours in the afternoon, which is typical around land masses, and picked up harder than before. In 15-20 knots we prepared ourselves for our first night at sea.

The wind was picking up, the waves were growing, and the setting sun felt ominous in the west. We had been out of sight of land for hours now, becoming gradually more nauseated, cold, and wet. There was a religiosity to those feelings, though, and we were filled with a reverence for the elements that we knew to be a rare feeling. I was torn at this time as at many others between the need to shout with joy and the inability to hold back tears. I wore every item of clothing I could fit under my rain coat and bib, and was both miserably cold and damp in my limbs and grateful beyond words for the warmth that cradled my upper body. A fluorescent, divine orange blanketed our rocking world and the temperature dropped quickly, and we knew we had less than an hour of light.

The chaos of the waves was difficult to decipher in the growing darkness, but I became suddenly aware of a foreign movement. Dolphins! They were jumping out of adjacent waves and rocketing toward the boat, running up the other side and playing along the bow. These were unlike the bottlenose dolphins we had grown accustomed to, who love to investigate and swim alongside our boat. These were smaller and darker, with a mottled gray pattern along their sides. Their dorsal fins were as sharp as little knives, and they dove and leapt with intense purpose. These dolphins were tough, quick, and otherworldly. They disappeared into the darkness around us as the sun determinedly set, and their supernatural world sprung up around us.

As dusk became night, the stars grew bright and eerie, filling the sky with a mirror-like blue light. There was no moon to dim them, and they danced in clouds around us. Replacing the sun in the west was Betelgeuse, followed by a parade of smaller, whiter stars. Each made its slow march down into the horizon, drawing with it another minute or hour. I don’t know the names of any constellations, so I used a few bright patterns as reference to check the progress of the boat. In the west were, to my vocabulary, the stingray and the raccoon. Farther south was the chicken foot, which ambled west as the stars rotated around us into the night.

The wind was turning on us, falling from a comfortable west to a more challenging north. The self steering system only steers us in relation to the wind, so as the wind clocked around we followed, turning from south to west over the hours between sunset and midnight. West was not a direction we planned to travel in, and I was faced with my first real challenge of the trip. The self steering would have to be re-tuned if I changed direction, and without Haden’s help I was not confident in my ability to make that adjustment. I would likely end up steering by hand for the rest of my watch, which would require a lot more energy and intention. Not only this, but we had been warned against fighting the wind. To fall off course for a few hours means very little in the long run, and I knew that the wind would return to north in a few hours. If I changed our orientation to the wind, the waves would break differently and the boat might take more of a beating as a result. It was much more important to me in that moment that I let Haden rest. So I let us turn west until it was Haden’s turn to take watch.


I thought about gybing us around and heading East, but decided that switching the self-steering system to the other side of the boat was dangerous at night. Without a mainsail up we couldn’t heave to, so the self-steering system was the only way we could keep the boat on a comfortable course without someone at the helm. I wanted to keep that system in case something happened and we both needed to go below. So I took the tiller for a little while and drove the boat on a broad reach by hand. Our heading eased around to the SW. Our speed was 3.5 knots. We were going in the wrong direction, but it was better than pitching and rolling going dead downwind. We stormed off into the middle of the night. I lay back on the cockpit bench with my head supported by the top of the engine well hatch. I steered the boat on a course by keeping the mast between certain stars. I don’t yet know the constellations so I made up my own. I knew I was heading SE if the constellation that looked like the state of Alabama was just above our starboard spreader. I watched the faint blinking light of the US Air Force tower pass miles away on our port side. Its blinking white light barely showing over the tops of the rolling waves.

I got tired of holding the tiller after two hours and let the self-steering system take us back on the westerly course while I rested. I sucked on a gummy bear to keep me awake. I think it also helped with the seasickness that I was starting to make me feel unsettled. The wind picked up just like the forecast had said. I watched our speed on the chartplotter start to hit 5 knots, still sailing with just the storm jib. That’s fast.

At 04:00 I took another round of seasickness medication. Emily woke up and came on deck to relieve me. We looked at our course and agreed that keeping the boat steady and getting rest was our top priority. We’d figure out our course at dawn. I went below and tried to sleep. I couldn’t. I got up at 06:00 and came back on deck because I was feeling sick in the bunk. I lay down next to Emily while she kept watch.

I looked off to the east and saw a strange orange tower poking up over the horizon due east. “Emily, is that a ship’s tower or what?” I asked. A minute later we could see it started to curve and we knew it was the moon rising. It was reddish orange with dark purple glowing around it. A huge sliver just on the horizon. This was the second awesome moment of the trip. The third awesome moment would come in about 3 hours. I closed my eyes and tried to sleep on the rolling cockpit bench. I couldn’t.

I’d open my eyes every 20 minutes to catch a glimpse of Emily at the helm. The sea was starting to turn a blue grey as the sun started to rise. I’d wanted the sun to rise so badly while I was on watch, but now, knowing that we were still 100 nautical miles from Tampa, and having gotten no sleep, I was feeling a little defeated. The seas had picked up considerably and Emily was steering to try and make our course over the waves a little more comfortable. I closed my eyes again. When the sun finally came up, I sleepily looked at the chartplotter. Our westerly dogleg had taken us way off into the Gulf. “We’re a long way from shore,” I said, “and a long way from Tampa. We should gybe.” Emily agreed and we gybed our single sail over the the other side. Now we were on a port tack and we were finally headed toward land. I sat up and took the tiller. I needed something to focus on as my seasickness seemed to be getting worse. I took a caffeine pill and Emily went below to sleep. The waves started to grow. The wind picked up even more.

The morning of March 14, 2018, I spent 5 hours steering our little Cape Dory away from massive disorganized waves that were cresting and breaking all around us. The third and final awesome moment was sitting by myself steering our little boat in winds gusting from 20-30 knots in waves that seemed to be 8-10 feet. A set would rise up on the horizon and I’d start steering the boat down wind trying to get the stern of the boat facing the wave. We’d drop down in a trough as the first wave rose up over the top of the back railing. I would nervously watch the crest of the wave as it towered over us. Somehow the crest would slip just under the stern and we’d race down the backside of the wave. At one point I clocked us at 8.5 knots racing down the back of a wave during a strong gust. I looked across the waves as the wind blew the tops of them sideways. Spray skipping along like a sideways rain. There wasn’t a cloud in the sky but I was hating the conditions. This is unsafe and I don’t like being here, I thought, but I wouldn’t want to be anywhere else. One huge wave swept us sideways when I couldn’t get the stern turned quickly enough. It broke gently over the rail of the boat and completely filled the cockpit. I stood, knee deep in water, while the cockpit slowly drained, praying that another wave didn’t come. Another one like that right now would go right into the cabin, I thought. Thank God she drained herself of the crystal clear water and we didn’t take another wave like that for the rest of the trip. I poured the water out of my boots and sailed barefoot the rest of the trip.

Around 11:00 Emily came up from below. She looked miserable. “Everything is wet,” she said. “The waves over the deck have come in the vee-birth hatch and drenched the bed. My pants are soaked the inside of my jacket is soaked. We can’t do another night like this.” “I know it sucks,” I said, “but we’re 80 miles from land in all directions. We’ve got to figure out how to make it through another night.” She took a caffeine pill, drank some coca-cola, and hoisted her wet clothes up the main halyard to flap in the wind above the crashing waves. They dried in 30 minutes. We sat in silence for the next 3 hours as we continued to roll through the waves and the wind. The sun beat down and we were thankful for a little warmth against the cold north wind.

At 14:00 Emily took the tiller and I went below and nested in the wet bed for a couple of hours. I tried to sleep but I still couldn’t. Lying in bed I half hallucinated waking dreams as the boat pitched and rolled. I was happy but starting to feel delirious. I got up at 18:00 and sat in the cockpit. The wind was finally down to 15 knots and the seas were settling. Thank God, I thought. “Let’s put up the main and try to set up a self-steering system for a broad reach to carry us through the night,” I suggested. Emily thought we should twist the main around the boom a couple of times to fake another reef point. We tried it and it worked. Fighting the boom and the main in the rolling waves was difficult to say the least. I pinched the pad of my index finger, not noticing until I started to see spots of blood on the sail and lines. It wasn’t bad though. Emily got frustrated trying to keep the boat head to wind with just the jib as I fought with the sail. It was the closest we came to getting upset but we kept our cool and got it rigged up. Once we got the main up I immediately hove-to.

Heaving-to is our favorite thing in the whole world right now. To heave to, you take your full keeled sailboat, with a balanced main and jib, and point her close to the wind with the sails trimmed in fully. Then, the easiest way to do it, is to tack over without switching the jib. Then you push the tiller over to the lee side and lash it. The backed jib pushes the bow off the wind while the tiller and main push the boat up into the wind. The two forces counterbalance and the boat sits, parked at sea. We move at 1 knot, drifting sideways, when we’re hove-to. A slick of cooler water, turned up from the keel, extends upwind calming the waves. The orientation of the boat to the waves causes the boat to gently roll with a high rail, protecting us from breaking waves. Oh my God, that feels good!Emily and I immediately started feeling better. I sat and ate honey oat cereal and watched the waves while Emily organized the cockpit and filled water containers. What a feeling! Finally getting a reprieve from the rolling and pitching. I’m never sailing without at least a little mainsail again, I said. I wish we could have done this this morning. We made a plan to definitely put two more reef points in the main when we got to Tampa. We unlashed the tiller and the Cape Dory slipped downwind and calmly gybed.

We set a course for Tampa and trimmed the sails. We got the sheet-to-tiller system set up for our sixty mile run hoping that the wind would let us hold the broad reach the whole time. I held the first watch. The sun set and stars slowly began to emerge in the grey purple sky. The waves were down to 1-2 feet and the wind was a comfortable 15 knots. I finally felt totally comfortable with the boat, and the trip. Confident and comfortable. We were in for another moonless night and I thoroughly enjoyed rocking beneath a breathtaking array of stars. I still had all of my foul weather gear on because the occasional wave would hit the bow wrong and send a coffee mug amount of water into my lap. About two hours into my shift I had a wave throw water on me that was full of phosphorescence. I watched the glowing droplets drip down my bibs. This was the first time I was really present to how incredible the trip was. The conditions were such that I could start thinking of our voyage beyond the immediate task/situation at hand. Here we are I thought. 50 miles off-shore and 40 hours of open water under our belt. At our current speed we’d reach Clearwater at 09:00. Around 20:30 I started to get really tired and I rested my head on the cushion. 15 minutes later I sat up and saw a fogbank rapidly approaching off our stern. I turned and looked forward and there was another fogbank ahead of us. This is spooky, I thought. The fogbank ahead of us was glowing orange. I stared into it, wondering how the wind could be blowing 15 knots and not blowing away the fog bank. I thought about ghost ships and ghost pirates and decided that we were definitely in for an encounter of some kind. But, as I watched, we kept approaching the bank but we never got to it. I realized it was an optical illusion of the waves and the horizon line.


I’ve never felt so close to the supernatural as we did on this passage. Evil seemed to lurk in the darkness between the stars. Demons were omnipresent in our dreams. A hallucinatory fogbank felt surreal and at the same time exactly correct. It was impossible to tell what was our perception going awry and what was simply bizarre and unknown.

When we finally sighted land after dawn on the 15th, we felt an incredible relief. Even with hours to sail before reaching land, we were finally in comfortable territory, sailing adjacent to a visible land mass. The open Gulf is a creature of its own, and oblivious to our very existence. Land calmed us, and we were able to rest and eat in relative comfort. We entered Clearwater Beach through Clearwater Pass and anchored in a small community of live-aboards and other cruisers. People filled the nearby shores, cars whizzed down the bridge adjacent, and motorboats buzzed through the water around us. An almost overwhelming array of sounds rocked us almost immediately to sleep.

Since then, we have been staying in Tampa with my parents, who have missed our company since we began work on the boat in January. We will stay here, completing projects, for a few more days, before setting off down the coast again.

With love and gratitude, we wish you all calm seas and fair weather —

Haden and Emily

Panama City to Carrabelle, FL

Haden and Emily, aboard the Hard A Lee, reporting on The Adventure thus far:

1:22 PM
6 March 2018
Carrabelle, FL

Ten minutes before sunset on Thursday, February 22nd, 2018, we set out on the Hard A Lee. We left Haden’s family in Panama City under full sail, and spent an hour making our way to the Saint Andrew’s Bay Pass, expecting to set out into the Gulf in the morning.
We had spent a month living on the Hard A Lee already, so we were comfortable sleeping in the small forward bunk, the V Berth. What was unfamiliar was the choppy rocking of the boat in the fifteen foot-deep water, the new gentle sounds, and the near-total darkness. Our little anchor light glowed at the top of the mast and we slept well.
The next morning we awoke to a bright sunrise, made coffee on our alcohol stove, and set out for the pass. Emily took the helm for her second sail in near perfect conditions. The wind was right for our exit south through the pass, and the sails filled beautifully.
Narrowly skirting a fast-moving barge entering the pass as we exited (“We need you out of the pass, captain!”), we found ourselves at last in the Gulf. Two months’ preparation had preceded this moment. We had toiled through projects in carpentry, electrical systems, fiberglass, and completely re-rigged the boat by hand, spending twelve hour days in the boat yard. We had planned the first two weeks, aiming first for Crooked Island, which lies a short distance to the southeast of the pass. The wind on that first day was coming directly out of Crooked Island, which meant we would have to tack back and forth at 30° angles to the wind. Out in the Gulf, in beating sun and four-foot swells, we headed south.
Sailing upwind, the waves are choppy and unpredictable and the boat does not roll comfortably, but tosses and turns, fighting to fall off the wind. We admitted to each other that we felt the beginnings of sea sickness, but that was not enough to make us turn back. We drank water, applied sunscreen, and excitedly held our course. We made our first tack, both watching the horizon to quell the budding nausea. We were now aiming farther north, at a 60° angle to our original course. Unfortunately, a boat so small and heavy doesn’t behave well in these conditions, and the Hard A Lee was being pressed back by the wind almost as quickly as she was able to move forward. The ability of a boat to hold its course against other elements is called pointing, and we were finding that our well-provisioned little boat did not point well. Our second tack was almost parallel to the first, reducing the would-be 60° angle to nearly 180°.
Fighting the urge to press on, but realizing that it would take more hours than are in the day to make it even halfway to Crooked Island in such conditions, we decided at last to turn back. Exhausted, we limped back into St. Andrew’s Bay, sailed to a remote bayou, anchored, and fell immediately asleep.

Since that first foray into the Gulf with our little 25’ Cape Dory, we have sailed and motored nearly 150 miles, traveling from West Bay in Bay County to Apalachicola, to Dog Island, and finally to the Carrabelle River where we are sending out this report. We have learned that cruising sailors spend a lot of time waiting for the weather to be just right for a passage. We have also learned that cruisers generally don’t beat upwind for hundreds of miles. Instead, when faced with a strong headwind, we either wait for the wind to change, or we change our destination.

We have reorganized everything on our tiny boat at least three times in search of the perfect nook and cranny for each of our belongings, re-taped the rigging, tightened screws and tapped in errant hinges, and gradually made the Hard A Lee our home.

We have spent time with old friends and made new ones, with Haden playing music at every stop along the way. Every conversation with an experienced sailor leaves us with more advice to consider and a greater confidence that we are setting off on a grand adventure.

Now we are waiting for a cold front to pass through so we can make a safe passage to Clearwater, FL, 140 nautical miles southeast of our anchorage in Carrabelle, FL. We’ll be crossing our fingers for a comfortable breeze from the west next week.

Thank you all for your love and support at the outset of this grand adventure.

Wishing you calm seas and a following breeze,

Haden and Emily