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Old 02-03-2010, 15:38   #1
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Location: Saint Augustine, FL
Boat: 1975 Downeaster 38' Cutter
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Lightbulb Transporting My Boat - First Offshore, Overnight Passage (Long Read)

I have returned from the sea! This past weekend I took the first step in the long journey transporting Windsong from Inglis, FL to St. Augustine, FL. The trip will take me down the West coast of Florida, through the Okeechobee Waterway, and up the East Coast. The first leg was the long journey from Inglis to Gulfport near St. Pete, a total ride of about 90 nautical miles and well offshore. The entire journey is outlined in this picture:

Let me recap the story thus far. I purchased Windsong in July, 2009 from the previous owner, Paul, in Inglis, FL. Inglis is a small town on the West coast of Florida in a region called the Nature Coast. The Paul was kind enough to allow me to keep the boat at his house up the Withlacoochee River. I would visit the dock about every other weekend cleaning and fixing up the boat.

I am by no means an experienced sailor. I have only done a few day trips in very easy conditions. I've braved one squall, but it was in the Inter-coastal waterway in St. Augustine. The worst threat to me was running aground. Being an inexperienced boat owner and novice sailor, this is an intimidating boat to learn to operate. The first time I took the boat up the river the engine's cooling water impeller busted and caused the engine to overheat. Spew steam out of the expansion cap, which I first thought was a fire brewing down below. It was pretty traumatic for a first ride and my confidence in the boat went down, as did my overall spirits. I spent the next couple of months trying to diagnose and repair the problem, learning as I went along. Eventually we were able to get it fixed and running, things looked up.

I took the boat out a few other times and only on one sail, as it takes a long time to get out to the gulf from where the dock is up river. The tidal range of the river made it so low tide travel was too shallow for Windsong. Day trips had to be isolated to high tide range making going out difficult. Even when I stuck to this rule, I ran aground very hard on one trip and had to pay a good amount of cash to get towed off the rock I landed on. Many lessons were learned each time out. During this time I have done a lot of work on the boat, mainly beginning the interior rebuilding.

However, the boat needed to go somewhere and couldn't stay there forever. The drive up there began to wear on me and it wasn't an ideal area to learn to sail the boat. I plan to do a complete refit and refinish of the boat, which will take part mostly with the boat on land. I need to get it hauled out, but the closest facility to Inglis that Windsong can access (depth and mast height considered) is down in Tarpon Springs. I initially planned on taking it there to haul out and truck up to the St. Augustine area to work on, but I found myself with the time to take the long journey around Florida.

The trip to Tarpon Springs would have been a bit too long to arrive in daylight hours, so soon after I purchased the boat I realized I would have to do my first overnight trip off-shore just to take the boat out of Inglis. The shoreline from Inglis to Tarpon Springs is very shallow up to about 12 miles out to sea. If the boat sank, we could practically walk back to the shore from many miles out. So not only did I have to do my first overnight passage, but it would also be my first time out of sight of land as skipper of the boat. I also was still worrisome about the condition of Windsong and its ability to handle the possible beating of an offshore passage, and if the engine was as good as I hoped it was.

I spent a lot of mental energy preparing for the trip. I studied charts, waterway guides and all information available to me to plan my route and prepare for navigation. I purchased all necessary safety gear and upgraded some existing gear as needed. Eventually I felt prepared and ready to go, so I began to monitor the marine weather forecast each weekend I had potential crew for help.

After all of the preparation, I felt it might be a bit short just to take the one trip down to Tarpon Springs. If all went well, I would want to continue sailing it for a little while before I spent all the time on land. The thought of the doing the whole journey down the West Coast, through the Okeechobee Waterway and up the East was so alluring, I began to consider if it would be possible. The boat is not in very good live-aboard condition, but it good enough so that it is way better than camping at the least. She sails fine, and the motor has been performing well since I did a good bit of maintenance.

If I had to do an overnight trip to Tarpon Springs, I could just keep going and make it as far down as St. Petersburg with two days of sailing. So two weeks ago I began extending my already planned route down to that area and decided it would be worth the try. If I started the journey this past weekend, I would have my girlfriend in another week for her Spring Break to do the next long leg down to Ft. Myers. So I eyed the weekend and hoped for the weather. It was iffy for most of the week, with a lot of rain forcasted along with strong winds. I researched marinas and found a great one at Gulfport Municipal Marina. They had a decent rate to keep Windsong for the week and was easy to access from the Gulf. Here is the route offshore that we took (in purple). You can get an idea of the scale by using the size of Tampa Bay for reference.

I only had one crew member available, my friend Jeff who I had sailed with a few times previously. We met up on Friday to discuss the forecast and make the final call on if the sail would happen. The forecast was like this:


Northeast winds around 10 knots in the morning becoming southeast 10 to 15 knots in the afternoon. Seas 2 to 3 feet building to 3 to 5 feet in the afternoon. Bay and inland waters a light chop becoming a moderate chop. A chance of showers in the morning...then showers likely in the afternoon.

Saturday Night

Northwest winds around 15 knots. Seas building to 4 to 6 feet. Bay and inland waters choppy.

Northwest winds around 20 knots. Seas 4 to 6 feet. Bay and inland waters choppy.

It would be a bit wet on Saturday, but high tide was at 1:00 p.m., so we had time to wait to see if the weather would hold off. But as of then, the trip was on. If it got any worse we would call it off. I spent all of Friday mentally preparing and getting gear ready. I got last minute items from Wal Mart: a new fire extinguisher, a 3-million candle spotlight, a weatherproof lantern, a cushioned chair for the helm, a spare fuel tank as well as food and snacks. My mind was buzzing the whole day, but I felt ready.

Unfortunately I did not sleep a wink Friday night thanks to the anticipation and constant scenario analysis. I really needed that sleep but had to deal with what I could get. We left Orlando in the morning at around 9:00 a.m. and arrived in Inglis at 11:00. Both of us over-packed with a ton of items. We figured out every possible scenario we could think of, and brought the gear to be prepared for them. We had the room, so it didn't matter. After loading we spent time getting things in place and in order, cleaning up a bit, checking the engine, and making final preparations. We spent a moment absorbing our final moments in Inglis and then at 1:00 p.m. we were off.

The ride up the river was uneventful, and that is a good thing. After the inlet to the Gulf, there is a narrow channel to take out to deeper water, some 3-4 miles out. At 2:30 we arrived at marker # 1 at the end of the channel were then able hoist the sails. The air was around 50 degrees, winds out of the Northeast around 10-15 knots. Here are the pictures from the start to marker #1.

Up the river:

Approaching the inlet:

Narrow channel leading out to deeper waters:

Marker #1:

Here we hoisted the sails and had a downwind run to the Southwest. We cracked open a beer to celebrate getting out of the channel, and made sure to share one with Poseidon for good luck.

Jeff and I traded hands at the wheel for the next hour or two while we both got situated with some food. We called our respective loved ones to let them know our location since we were unsure if we would have cell phone reception much further than this.

As the wind began to turn more from the North, we reached our second waypoint at 3.7 nautical miles from Withlacoochee marker #1. There we turned South-Southwest towards the next buoy, some 10 nautical miles away. We were now on a dead downwind track, so I decided to try using the whisker pole to hold the jib out allowing a wing to wing sail set up with the main and jib. I had read about the way to rig it but that was a while ago, so I gave it my best shot. Once I got it set up (although I think I was missing a line or two) it seemed to work fine and we were being pushed along at a smooth 4.5 knots.

Around this time Jeff's stomach began to disagree with the motion, so he took the time to get some rest. We took some ginger tablets made for seasickness before we left. I'm not sure if the helped me or not but I felt fine. It was sometime on this leg that we ran out of sight of land. We could see the power plant at Crystal River for a long time, however.

Once we neared the next waypoint the sun was coming lower on the horizon, and the moon was poking up from the East. Jeff was feeling a bit better after some rest, and now we turned South-southeast on a broad reach, a bit more comfortable than the rolly straight downwind sail. I had been eying this rain system in the West that was covering up the sun. I worried that it was coming to soak us after dark, but the rain ceased just in time for a perfect sunset.

Moon rising:

Sun setting:

It was a fantastic ending to the day. It never really seemed to get darker than that though, as the clear sky allowed the almost-full moon to shine down. It was like a powerful spotlight illuminating the water, the boat and the sails. The stars were out as well, and I used the ones in front of me to steer towards so I didn't have to light up any electronics or the compass. It was bliss, and what I always dreamed sailing at night could be. We both had a lot of nerves once the night came around, but the bright moonlight lifted our spirits and made it a bit more comfortable. The picture below is a long exposure shot of the moon. There is no sun out anymore, it is completely nighttime. But the moon was so bright, somehow the sky was a daytime blue in the picture. We were stunned and had to double check the timestamp.


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Old 02-03-2010, 15:39   #2
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Boat: 1975 Downeaster 38' Cutter
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My worst fear was that we would be caught in a lot of rain at night with no visibility and wet, cold, miserable conditions. This was far from that, it was perfect. Well, I could have had a bit more of a meal than a pre-made Publix ham sub, but it was decent for the lack of preparation needed.

The winds began to die, however, and we slowed to a crawl at around 2.5 knots. I knew the winds would be picking up out of the Northwest sometime overnight or Sunday morning, but had no clue when. I began to worry that at this pace, we wouldn't make it down to Gulfport in the daylight to pull into the marina and meet our ride out. So I cranked the motor and pushed along for about an hour and a half. I really wished I could have been patient and just sailed slowly and peacefully, but I felt the need to keep on schedule and to the plan. I hoped to stay close to a 5 knot average the whole trip, 4 at the minimum.

We motor-sailed along at about 6.5 knots and brought our average pace up a good bit. After dark we made sure things were neat and tidy around the boat. I considered reefing in the mainsail (making the sail area smaller in case of heavy winds) so I wouldn't have to do it on deck at night if needed, but decided against it since the wind was dead right then. This would come to be a stupid mistake later on.

When I noticed the winds finally had switched and come up about 10-15 knots out of the Northwest, I stopped the motor and we were sailing a good 5 knots. Jeff took the help at this time so that I could prepare for a long night shift. We both agreed that since he usually goes to bed earlier than me, I would take first watch. I rested up a bit and was able to find reception to call my parents and Jenny briefly. This was around 9:30 I believe and we were moving South-southeast back towards land. I brought along my backpacking stove to make some coffee so I brewed a large cup for my watch. I prepared another sandwich to eat later, my ipod and all of my safety gear. For nighttime we made sure to have on our life jackets on, safety harnesses tethered into the jacklines at all times, headlamps, emergency strobe lights and whistles, etc. Our biggest fear was a man overboard as it would be very hard for one person to get back to the person. So we took all precautions.

At 10:00 I took on the watch and Jeff began to settle down for some sleep. If I needed to wake him I would yell, shine the spotlight at him, and maybe even blow the air horn if need be. The wind was slowly picking up and we were churning along at a good 5.5-6 knot average now. The seas were also picking up and the waves were coming from behind us. They weren't too large yet, but they were very close together. They would come up under the boat and the boat would try to lurch to the right, up the wave and into the wind. This was a heavy motion and took me a bit to get used to, but once I did I was able to anticipate the waves and compensate with the wheel to steer straight and keep control. I was a little nervy at first, but once I got it it was incredibly fun. I've never sailed in more than 15 knot winds, and they were now picking up close to 20. Around midnight we came near Anclote Key outside of Tarpon Springs and were were finally close to land. The rest of the trip would be hugging the coast line around 2-3 miles out. There were tons of buildings and towers now, so lights littered the horizon providing even more comfort.

Over the next 4 hours the wind kept coming up and the waves grew with it. I was having an exhilarating time sailing so fast, now surfing down waves big enough to launch us to 8.5 knots at times. That is way above the hull speed of 7.3 knots. This is a big, heavy, tank of a sailboat and to have it go this fast is a big deal for someone not used to handling it. I felt like a bat out of hell and was having the time of my life. I did realize at this time (around 2:00 a.m.), however, that I really should have reefed the main before dark. We were overpowered at this time and things were only getting crazier out there. The waves were getting bigger and bigger, and steering became more intense. I knew if I had to go out to reef the main, it would be a scary event. At around 2:30 a.m. the stay-sail was caught up on the jib lines and was becoming erratic. I decided it was time for some rest after I fixed the sail, so I woke up Jeff to take the helm. While he was getting ready things seemed to get even more intense so I hurried him up, nervous about the beating the stay-sail boom was giving the deck.

Once he was at the helm I strapped up and fixed the problems up front. It was wasn't too bad going up on the deck, but Jeff had just woken up and was tossed into a difficult steering situation. As he was getting used to it I was being lurched around on deck, basically crawling along on hands and knees holding onto the handles as hard as I could. I eventually fixed the problems and went down below to attempt to get rest. I called my dad one last time to confirm we were OK and that we were now near land.

It had occurred to me at some point that we were now flying along so fast, that at this rate we would make it to Pass-a-grille inlet, our destination to come inland, a few hours before dark. This was pretty ironic considering my nerves about the earlier light winds, and motoring through them. How to stall for time was something we needed to plan, especially considering it got very shallow any further south of the inlet towards the mouth of Tampa Bay.

I had no luck getting any sleep with thoughts of how we would stall and the general nerves of not being up top watching over things lurked on me. I could feel and hear things getting more chaotic up top, and knew we weren't too far away from the inlet. At around 4:00 a.m. Jeff told me we had arrived, and we had to quickly decide what to do. We could go south for a few more miles before we would have to turn west. We decided to do that for a bit and I tried to give sleep another attempt before daylight. Before I turned in I went on deck to take down the stay-sail. It was a wild ride on deck, but I got the sail down quickly.

Soon after things became a blur of adrenaline and nerves. The weather got worse and worse and we decided we needed to get out of these crazy waters and turn back towards the inlet. I pulled out my new 3-million candle spotlight in hopes that we could find the channel markers at night. As we tracked back, we found ourselves pointing too close to the wind, unable to sail. Even so, the wind was howling now with 25+ knots. There was no getting around the fact that I needed to take down all of the sails. So we cranked the motor and I got ready to head out on deck again.

We were now pounding into the waves, which were a good 7+ feet with a quick period, sometimes less than a second before the next. It was like going into class 6 rapids on a whitewater river. I crawled up to the mast to take down the mainsail, hugging the mast for dear life anytime I felt a wave lurch under us. I had the sail down quickly, but tying it up took a little time. I didn't have the sail ties with me so I just used a spare line I had for these kind of things.

After the mainsail was down I crawled back to the cockpit to roll in the jib, the last remaining sail. As if the ocean decided we needed to be tested further, I found the roller furling completely jammed. I was unable to roll in the sail, and if I couldn't figure it out I would need to somehow wrap it around itself by hand, up at the bow, plunging into the waves...scary thought. I realized the jib sheets were tangled around the flag hoists, so I ran up to untangle the horrible knots they were in. This had no effect on the roller furling, so I began to get extremely worried what would happen if we couldn't get the sail down and needed to go into a narrow channel. I did the only thing I could and went back up to the deck and onto the bowsprint. I ran up there to fiddle with it, cranked on the roller line and made sure all other lines weren't tangled on anything. This was easily the most terrifying moment of the night, and one of the most of my life. Seeing each wave come at me one after the other and splash over me as the bow plunged into them is something that is burned into my brain. If I fell out Jeff would have had a near impossible time getting back to me. I held on tight, grit my teeth and did what I could though. Unfortunately, the jib still wouldn't roll in. To help things, we angled more Northeast so the jib was holding wind and helping us along, instead of flapping wildly. I made it back to the cockpit and we motored uncomfortably in the washing machine towards the channel entrance.

When we got to the entrance I began to shine the spotlight to find the markers, which were easily spotted with the light. We were both relieved that seeing the channel wouldn't be much of an issue, particularly with my GPS chartplotter never letting us down and pinpointing us accurately. There were breakers on each side of the channel leading in, a clear indicator that we better stay on course no matter what.

As if on queue, we neared the entrance to the Pass-a-grille inlet and light began to show on the horizon. The land began to surround us and the water calmed into near-glass. Our first protected waters began right as the sun came out and things calmed down.

I don't have any more pictures for the night-time part of the journey. Mostly because my camera is horrible at night pictures and Jeff was passed out. Once he was up he needed to be at the wheel while I rested, and then things got interesting so cameras were the last thing on our mind. But once we entered the channel to the sunrise, we had to snap shots in relief and celebration.

Moon setting:

We were both in awe that we made it, and took the moment to absorb the accomplishment and the beautiful scene. We motored slowly into the channel and up towards the Inter-coastal Waterway. As the light continued to grow and waters calmed, I walked up to the bowsprint and was able to roll up the jib by hand. I still need to figure out whats wrong with it, but at least the sail is rolled. I surveyed the damage up front and noticed both jibsheet lead blocks shattered at some point during the last battle upwind, and the whisker pole topping lift broke while holding the stay-sail boom in place. Things were a mess on deck, but inside everything was chaos. All items we had neatly stored was thrown about, in particular all the tools, spares and hardware up front.

Soon after we arrived we had to cross under a draw bridge to the main waterway. As it closed we felt like we were finally safe, the craziness of the Gulf behind us.

I called up the marina to see if we could come in, but they said the tide was pretty low for my draft to approach. So we decided to anchor out in the bay to clean up, rest and relax before the tide came in. This was about 7:00 a.m., and we had to wait till about 11 for the tide. Jenny wouldn't even be coming until 4:00 so we had a lot of time to kill. Cleaning up was in order along with a small breakfast.

At anchor:

Dolphins around us:

looking at the chaos up front:

The bed:

After some cleaning we both sat around relaxing with a hard earned drink enjoying the breezy anchorage. It was a beautiful day, perfect for reflecting on the amazing night. We discussed the highlights, lowlights, what we could have done better and admired how much confidence we now had in the boat. We were going to paddle the dinghy up to a restaurant near the anchorage, but the wind picked up making a paddle difficult. We decided to wait for real food once we dock.

I sent Jeff out on the dinghy to take some pictures of the boat while I held onto a line:

Dirty dirty boat

At 11:00 we pulled into the marina and docked at the floating transient dock. We had some trouble attempting to turn the boat around in the tight basin, particularly with the wind beating us back towards the dock. Eventually we gave up and decided to try when the winds were better the next week. We tied up tight, attached the shore power cable and I did my paperwork in the marina office. After a bit we walked up to the same restaurant we saw from the anchorage and had a good meal. By this time we were finally feeling a bit delirious as the lack of sleep and nutrition caught up to us. The meal was delicious but we were out of it.

We returned back to the dock and Jenny called to inform us she was able to get out of work early and was on her way. We finished packing and then waited out the remaining time chatting with other boat owners in the marina about Windsong and our journey. She will remain there for the rest of the week and I will visit her once before we leave next Sunday. I need to figure out the jib furler and replace some of the broken hardware. I'd also like to give her a good scrub since she is finally away from the swampy waters.

It was an incredible journey and it never failed to deliver a memorable experience. I feel much more confident in Windsong and myself as a sailor and feel I have accomplished a huge goal. With this experience, the rest of the journey around Florida seems like it will be a piece of cake since I have the ICW to travel in. The worst that could happen is I crash into a boat or land, but at least that is better than something going wrong way offshore in the middle of the night. Definitely looking forward to getting back to the boat and continue this adventure.

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Old 02-03-2010, 16:06   #3
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A friend and I used to shuttle a Downeaster 38 from Florida to New York and back. They are indeed built like tanks. A Downeaster is a perfect example of the maxim that "The boat can take more than the crew can".
Sail Fast Live Slow
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Old 02-03-2010, 18:00   #4
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Great story. I am a new boat owner as well. Although I am a bit luckier in away because my big trial by water will be on Lake Erie.

I look forward to reading more about your adventure.
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Old 02-03-2010, 18:45   #5
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Nice story. The first trip is always the most memorable. You might try running offwind to lighten the pressure on the jib so it furls easier. If ya have to go up on the sprit, running offwind for the task makes it smoother and a lot less hairy up there. Having gone through something similar in 50+ a few times proved that to me.
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