Sat : OK start in light breeze, a little behind the other SPs because I had to wait for a catamaran that squeezed in next to me on the beach. Savannah Dan and Paddlemaker (SP21) pulled ahead at first by row-sailing in the light SE breeze. Put up the mizzen staysail and passed all the SPs in just a few minutes, also passed Crazy Russian in his inflatable catamaran. Had to round up to correct a rigging mistake, and then again to take the staysail down as we turned down the coast once in the Gulf, thereby losing much of the 500 yd lead I had built up. When the wind died I row-sailed to keep up speed, but Coconutman and Mikey111k (SP21) slowly passed me by tandem row-sailing effectively. Roo in his EC22 started heading further out, evidently to find wind. Coconutman did the same, and before long they were barely visible.

I row-sailed from about 10 am to 2 pm, which put me pretty much out of sight of the two SPs behind me. Several Hobie AI-type craft peddle-sailed past me with seeming ease. After sailing for an hour or so, I rowed and row-sailed again for hours. Frayed Knot (Hobie AI) passed me again after dark somewhere around Venice.

Sun: Reached Stump Pass just after midnight and took 2 hrs to get through to the ICW in Lemon Bay against the strong outgoing tide, succeeding after three tries by dragging the boat along the S shore. This was exhausting, but two could have done it pretty easily. Rowed virtually all the 6 miles of ICW from Lemon Bay to CP 1 in very light and shifting breezes. Altogether at that point I figured I had rowed 16 hours since the start of the challenge. I was surprised at the checkpoint to see that Roo and Coconutman had not reported in yet, as I was sure the Stump Pass agony had put me near or in last place. I rowed back under the bridges and put the masts back up, and spotted Coconutman and Mikey coming in. They said Roo got held up in Gasparilla Pass by the tide, and maybe a sandbar.

From Placida I sailed S down generally along the ICW, using the staysail well for about 30 min before wind clocking to the SE became too close. Progress was fine until somewhere around Useppa I began to have to tack. The rest of the day was (to me) miserable sailing in light to moderate headwinds with scorching sun and continual powerboat traffic chopping up the water, causing me to alter headings. The relatively poor pointing ability of the Pearl and my own maddening tendency to pinch or sail too high was driving me nutty. One of the circles in Hell may be devoted to this kind of sailing.

Looking at the chart I decided Pt Ybel at the E end of Sanibel Is would be a good place to sleep before heading back into the Gulf. Big mistake: there is a park there, and people were all over the beach until well after dark. Worse still, powerboats run by there constantly, and their wakes tossed me around for the several hours I tried to sleep. I was there from about 6 pm to 9 pm and never slept a wink. My thought had been that it would be irresponsible to enter the Gulf with no sleep since the start of the race, because the nearest pass (Caxambas) that I had actually been into was nearly 40 nm away. This may have been excessive prudence on my part, because no serious weather had been forecast. As I headed into the Gulf around 9 pm the wind became very light, causing me to row and row-sail for about an hour and a half before giving up in a dead calm. I told Ron on the phone, I know I cannot row to Key Largo, so I've about had it with rowing. I tossed the anchor over in maybe 25 feet of water and tried to sleep without putting up the camper. I'm sure I nodded off some, but I was cold and jumped up every time the booms rattled to see if there was wind. There wasn't. The water was smooth as glass, beautiful in the moonlight, but there were very shallow swells that rocked the boat now and then.

Mon: At 2 am I heard the booms rattleand sat up in a very nice E breeze of probably 6 kts and building. For a glorious hour I sailed with the staysail up making at least 5 kts. When the wind clocked to the SE the staysail came down and I had to tack some, but it was wonderful sailing compared to the trash I endured the day before. By early afternoon I was at Caxambas Pass. Winds were bad in there and I had to tack and row-sail again to get through in four hours, about the same time it took Ron and me last year.

All afternoon I sailed E toward Indian Key in a SSE breeze. At one point I tried the staysail, screwing up every way possible, starting with rigging it incorrectly, falling in the boat, jibing accidently, getting hit with the boom, and running aground. As it turned out, the wind was too close to use the staysail, so I had to haul it down.

Sailing into Indian Key Pass in the late afternoon, near the G "7" marker where it gets narrow, I happened to glance behind me&emdash;Roo and Tinker were 200 yards away in Southern Skimmer running me down, with a spinnaker yet! I was stunned, because I had glanced back a time or two and had never seen them. They passed me, as I always knew they would, and we headed up the pass against the outgoing tidal current but with the S wind. Moments later Salty Frog, an excellent kayaker who eventually was the first EC09 solo finisher, passed me with an easy, beautiful tempo using a Greenland-type paddle.

Getting up the last three miles of the channel was a desperate battle for me. I needed both the oars and the sails to overcome the strong current, but I had great difficulty keeping the boat straight. Just moving to the rowing position caused me to veer off course, and I had to choose between rowing frantically to try to straighten out, or leaning forward to hold the oars in place with my chest on my legs and trying to yank the tiller with the steering lines rigged on my port and starboard. Of course when you slow to a stop and drift backwards the rudder is useless anyway. I ran aground numerous times, falling behind Roo and Tinker each time, who were skillfully using the sails and oars to make turns and steady progress. I guess this went on for nearly two hours, but just before dark I was about 500 yards behind Roo when they started sailing across Chokoloskee Bay to CP 2 three miles away.

I may have been dragging my rudder row-sailing across the very shallow Chokoloskee Bay, or perhaps it was just the tidal current that made it so hard to attain any speed. In any case, Roo and Tinker were gone when I arrived at CP 2, and Salty Frog was setting up his tent on the bank to get some sleep. Roo's speed at clearing checkpoints is well known, and in this instance he had the incentive to hurry and try to catch the last of the outgoing tide to get through the five miles of mangrove channels that would take him back to the Gulf. I found out later he and Tinker did manage to escape on that tide, and caught a nice fair wind to take them S along the coast all night.

Despite my difficulties, I know now that at CP 2 I was in a pretty good position in the Challenge. The amazing Lumpy and Bumpy had already won the Challenge, and the eventual second and third place finishers were well ahead of me, but the closest sailboat behind me was 7 hours back, and I was 28 hours ahead of the only remaining SeaPearl (Running Mouth had to drop out before CP 1, and Coconutman and Mikey111k dropped out late Sunday or early Monday). Here, though, my race plan and aggressiveness cost me dearly.

Unless safety considerations called for a different approach, as they would later, I was determined to push myself to my limits. Thus, even though I knew well that the conventional wisdom called for resting through the imminent incoming tide, I believed I could make it to the Gulf against the tide, and set out to do so. I progressed satisfactorily at first, but as I entered the mangrove channels across Chokoloskee Bay I began to struggle. The tide and S wind were against me, and I again had trouble keeping the boat straight. As I inched along rowing strenuously, the boat would turn and almost spin on each side of the current. One unanticipated result was that my GPS would not give me a reliable heading. Sitting backwards I had difficult knowing where to go after spinning a few times. At one point the boat was swept into mangroves and I received a shower of leaves and sticks (as well as some snails, I would discover in the morning&emdash;symbols of my slow progress at this point). I couldn't see my boat compass from the rowing position, and I had to read the barely visible kayak compass between my feet upside down. The moon was bright enough, but the grayness of the light and fatigue made all the channels look the same. I began to wonder if I was lost. After rowing from 9 pm to 2 am I tossed the anchor, pretty much exhausted and extremely frustrated. The current was now too strong to overcome. I knew I might be trapped in one of the hundreds of mangrove cul-de-sacs in the area, and had blown a major portion of whatever lead I had earlier enjoyed on any competitors behind me.

Tue: I awakened at 5 am with a strong tide running in my favor toward the Gulf. After about 20 minutes of pulling I managed to free the stuck anchor, having almost decided to cut the rode. This incident made me glad I had overcome the temptation to leave my spare anchor behind to save weight. Rounding one bend I could see that I had actually made it to Rabbit Key Pass, which led to the Gulf. I rowed in still air until finally reaching the wide bottom of the pass, where I caught a light E breeze. By 7 am I was sailing clear of Rabbit Key, having taken ten hours to travel the 5 nm to clear the CP 2 area. By early afternoon the wind had become SE (a headwind for me), and eventually died. Because of the ordeal of the previous night and early morning, I was reluctant to row. After spotting the light near the entrance to Lostmans River, I tacked slowly and drifted for two hours before reaching it. I was only 16 miles S of Rabbit Key, and barely advancing. Around 2 pm, though, the wind picked up again. It was still a headwind, but it grew steadily in strength to perhaps 12 kts, and I was able to tack down the coast to Little Shark River by about 7 pm. The anchorage at the mouth of Little Shark River the is the last until Flamingo for larger boats heading S , so I sailed in to have a look. There was a trawler anchored there, and two larger sailboats further inside in the river. I decided to turn back out and use the last hour of light to sail a few miles further S to the mouth of Big Sable Creek. Ron and I checked it out a few years ago, certifying it for just the use I was about to make of it. It's shallow to enter, but no problem for a SeaPearl's 6 inch draft. I sailed in at dark around 8 pm, joining two outboard fishing boats. I had a beer and an MRE, and fell asleep at 9pm.

Wed: Just after midnight I got up and quickly got underway. The full moon was beautiful, and the wind was out of the E at perhaps 6-8 mph. This was a reach for me, and it was wonderful to slide quietly down the Cape Sable coast close to the shore without tacking. I passed two anchored sailboats in the next hour or two. The Cape itself sheltered them from the E wind, so they had no need for a more protected anchorage. By 4 am I had rounded East Cape and was sailing toward the red lights of the radio tower there about 10 miles away. I was sailing against a falling tide. In addition, the E wind was now a headwind, and a weakening one at that. It would not begin to strengthen until a little before I reached CP 3 at 11:40 am. Lugnut, the WaterTribe Captain at CP 3, told me that Roo and Tinker had gone "outside" on the southern route. I took this to mean the so-called yacht channel or shipping channel to Long Key, shown on the charts as beginning at marker R "2" S of East Cape. That route would add 30 miles to the standard easterly route taken by virtually all Challenge kayakers, and almost all sailors unless, due to strong E head winds, the longer narrow E-W channels on that route become impassable. [I found out after the race that Roo and several other competitors who passed me used a shorter alternative route through the large banks and shoals ] I determined to take the standard route, which promised to be the fastest. On the way to the first difficulty of the route, the infamous four-mile-long Tin Can Channel, I noticed that a more southerly route beginning W of Tin Can Channel was nothing but mud&emdash;absolutely impassable. The combination of E winds and full moon had made for an extraordinarily low tide. The wind was picking up fast, and I knew I could not get the boat through Tin Can Channel alone. Ron and I had spent 20 hours trying to get through that channel last year under similar conditions, and I think have a good feel for what is required to do it. At this point I made what turned out to be a very costly decision to turn around and head all the way back to East Cape to take the yacht channel. I reasoned that the wind would block following sailboats (but not kayakers) from passing through Tin Can Channel, and that the sooner I started on the long way around, the better off I'd be. I headed to marker R "2" without delay. Along the way the wind continued to increase, with gusts of 18-20 mph. Whitecaps were appearing everywhere, and I began surfing and pounding on four-foot seas. The wind was at my back. I had full sails up, and the boat was getting difficult to control. I managed to round up and heave to in order to reef (five in the main and three in the mizzen) and to fill my water ballast tanks. The boat behaved much better after that, but my problems weren't over.

I did not have the far outside route plotted out; it looked straightforward on the chart, and I never intended to take it anyway. The trouble this day, however, was that it runs SE. I would have to beat with very little sail up, and I would have to take the building seas on the port quarter or beam. If the wind shifted just a few degrees more to the SE, I would have to tack into the chop. I would have 20 nm of open water to cover once I reached marker R "2", so much of the crossing would be in the dark, and I had been sailing since midnight.

It was 4 pm when I turned SE. Right away I took some water over the bow, and every slap of oncoming chop came with at least a good amount of spray in the boat or on me. I saw no markers whatever, only whitecaps in front of me. For all I knew the wind would get stronger. Whether because of good judgment or lack of courage, I was not comfortable, and I turned back toward East Cape 2 nm to the N.

This was a very dark moment for me. The day had been a disaster of light headwinds, extraordinarily low tide, and menacingly strong E winds. I had wasted all afternoon, and now had 10 miles to go just to get back to Flamingo. For the first time the possibility of not finishing the Challenge occurred to me. The boat was still handling well, so I headed NE upwind as close as I could in order to recover lost ground instead of seeking shelter fÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿÿ