It seemed an eternity, but we finally passed Stump Pass shortly after dawn and began the slog to Gasparilla Inlet. Not long after Stump, John Bell caught us in his O'Day Daysailor II, something I consider no less than an awesome feat. John had trouble launching and got off the beach almost an hour after us (I think). That meant he missed the good hour of winds we had close hauled going down the coast before it went light. But he persevered all day and into the night. He tried to stop and sleep once in the open water, but found it too rolly and pressed on. He caught the two of us, who had been able to get several naps. We watched as his boat with full sail outpointed Oaracle by about 5 degrees.
We got in one long tack past Stump Pass when we found the wind increasing. Soon we decided to tuck the first reef in. About the same time, John first took in his jib and then reefed his main, which also seemed to erase the O'Day's ability to outpoint us. It wasn't long when we questioned whether the second reef should have gone in. The waves went from around three feet to around eye level - about five feet when sitting on the high side of a heeled Oaracle. Not much later, I was looking up at the waves as the sea and horizon disappeared behind the largest of them - six footers. If they had been breaking, they could have flipped Oaracle, but they were only whitecapping. The wind seemed to be at 20 or better, with some pretty good gusts. Oaracle would surge over a wave, down the backside and instantly rise to the next wave - the space between seemed only a little longer than the boat.
Once it was clear that the waves wouldn't tip Oaracle (as long as one didn't break), I began to enjoy the rugged sailing. Almost every wave flipped some water over the boat and into the cockpit and Scott, picking the relative lulls in the waves, kept the cockpit bailed. It was rugged. Spray was blowing constantly into our faces. There was some minor slapping as the flat bottom pounded over the wave tops. It was full daylight, or as full as it was going to get on a cloudy morning. Scott thought he saw a boat shoreward of us, but I couldn't pick it up. It turned out to be DancesWithMullet in his modified 14-foot Blue Jay, Mullet. He told us later he found the waves less treacherous closer to the beach - the opposite of what I'd expected but living only a few miles away he should know! At some point during this beat, noticing Scott seemed a bit nervous, I lied and said Oaracle had been in worse conditions. It didn't work; Scott told me later he wasn't fooled. (Well actually it was half true. Oaracle has been in higher winds, but never that combination of high, short and steep waves.)
We plunged on down the coast and caught a slight break as the wind shifted a bit westerly and we could almost, but not quite, hold course on a starboard tack. My concern now was successfully navigating Gasparilla Pass. The good news is the tide was with us; the bad was I have never seen the pass, not having used it on any previous challenges. The pass can be tricky, particularly in some types of heavy weather. It's typical for semi- or unimproved inlets along the Southwest Florida coast. The channel runs out the mouth and then turns south, with shoals to the north and west of the entrance. In some combinations of wind and tide, the waves can break completely across the entrance with no clear way in.
Scott manned the GPS and I continued to steer as we plotted our strategy. The charts show the shallowest water on the north side of the inlet but indicated that, with the rising tide, we should have at least four to five feet of depth if we approached from the west. So we planned to stay far enough offshore to avoid the shoals, but close enough so we could judge if it was safe to enter from the west. Scott plotted a careful course and we were able to stay clear until we could see that it looked safe to enter from the west. As we approached the mouth of the inlet, the water got smoother. The only slight hitch was once we hit smooth water, one of those weird waves, the kind that seemingly breaks forever came across the entrance. As it was only 12 to 18 inches high, I wasn't worried, but it gave Oaracle a good toss as it tumbled by. Not dangerous but a reminder never to underestimate the sea.
As we entered the narrow channel inside around 10:40 a. m., the wind was partially blocked, but our speed hit 6 to 7 knots, courtesy of the full flood tidal current. I suddenly understood why competitors in past years have had fits when they tried to contend with this narrow passage and a contrary wind and tide. We beached on a narrow strip of land to catch our breath and wait for John Bell, who was a few minutes behind. First, though, we got Dances with Mullet who had slipped in right behind us, and then John. We rung ourselves out, chatted about the hairy conditions, and then pushed off. The rest of the way to Checkpoint 1 was anticlimactic. We slid down the channel to the swing bridge bisecting the sound and waited a few minutes for it to open, during which PenguinMan and OceanDiva came up the Intracoastal Waterway.
PenguinMan and OceanDiva on thier tandem Hobie Adventure Island and John Bell on Alobar circle, waiting for the swing bridge to open at Gasparilla Sound.
The wind had veered enough that sailing through the bridge was easy and we had a downwind run (sparing us the need to row) through the narrow side channel to the creek that leads to the checkpoint. After a brief pause to strike the rig, we rowed to CP 1. The old bridge, the one with pilings so close that Oaracle had to be paddled through, was gone. The new bridge had enough horizontal clearance that we could row through with ease. A couple minutes past noon we were tying up at Grand Tours, the first checkpoint.
Our intent at this point was to go on, but not immediately. For one thing, despite getting a fair amount of sleep during the first leg, I was exhausted. Secondly, the wind was still blowing very strong, something over 20. I wasn't sure we could sail out the narrow side channel back to the ICW and I didn't think we could row, since it would be dead into the wind. To compress the rest of the day and night, I got a couple multi-hour naps, first in an air conditioned bunkhouse reserved for competitors and the second on Oaracle. Pat Johnson, who was following PlumbCrazy and picked him up when he decided to drop out short of Stump Pass in the worsening seas, made a generous offers. He suggested we might - since we had the time - bring the truck and trailer to CP1, which would shorten our trip from Key Largo to pick it up after the finish He offered to drive one of us back to the start (and also said he would drive us back from Key Largo). It sounded like a good idea and Scott did the honors.
We got up several hours before dawn on Monday and huddled - and discovered we each had some reservations about continuing. Scott was worried about the possibility - given what we had been through getting to CP1 - of more prolonged headwinds. A check of the weather radio gave a prediction (accurate as it turned out) of light to moderate fair winds that should hold to get us to CP2 at Chokoloskee but then headwinds would return and make it a long beat to CP3 at Flamingo, and possibly across Florida Bay to the finish. As for me, despite two multi-hour sleep sessions, I was still exhausted. Maybe it was because the truck and trailer were there and handy but we made the decision to stop at CP1.
Almost as an anti-climax, we had a very pleasant row at sunrise to the nearby boat ramp to take the boat out. The winds had subsided to a zephyr and veered to the north, and Oaracle skimmed along effortlessly under oars. About seven hours later, we were home. Where I slept for much of the next two days.