In Herb Payson’s Blown Away, one of the best sailboat cruising books ever written, he recounts how a friend hired him and his family to sail a boat from Tahiti back to California. Payson looked forward to it since unlike his fat cruising boat, this sleek craft would sail well to windward!

He wrote, “‘Sure she sails to weather,’ was a friend’s wry comment, ‘but how do you go to weather? That’s the question.’”

Gary's Oaracle at the finish line of the 2008 Everglades Challenge.

That was a question that got answered for most participants in this year’s Everglades Challenge. No, we weren’t crossing oceans. But most of the fleet faced half or more of the course hard on the wind, in shallow waters that encouraged steep waves. Tough on the sailors, it could be brutal on the kayaks and canoes venturing down the course.

On Oaracle, the answer to that question is: we did middling, and certainly better as the race went along. More about that in due time.

By way of background, the Everglades Challenge is a 300-mile expedition race open to small craft – canoes, kayaks, sailboats, etc. It begins at Ft. DeSoto Park on Tampa Bay and proceeds around the tip of Florida, ending at Key Largo. Competitors must stop at three checkpoints during the race. The requirement that all boats be beach launched from above the high tide mark and the difficulties of getting in and out of the checkpoints are “filters” that limit the size and capabilities of the boats. At one checkpoint you have to go under a low fixed bridge (mast down on the sailboats) with the pilings about 12 feet apart (too narrow for rowing), while at another the entrance is a multi-mile twisting path through mangrove islands where strong tidal currents rule. (Go to www.watertribe.com for a more complete description of the course, rules, and race classes.) We all also have tribal nicknames.

If you have Google Earth installed, click the image at right for an overview of the course.

Noel Davis, of Furledsails.com, was again crewing on Oaracle, as he had in 2007. He had contracted a nasty virus the week before that had settled in his lungs, but was feeling better and after a visit to the doctor decided he was well enough for the the EC. Oaracle is a 20-foot Jim Michalak-design Frolic2, a balanced lugger with small mizzen and which weighs no more than 350 pounds empty and probably around 1,000 with both of us and our gear and supplies. This was my fourth campaign in Oaracle; in 2004 with wife Helen (we DNF’d with new boat problems), in 2006 with Chuck Leinweber of Duckworks and in 2007 with Noel. Both of the latter two races produced finishes, winning the coveted shark tooth necklace and mini paddle awarded to those to make the 300 miles. Helen (Wingnut is her tribal name, but known to the crew of Oaracle as the Admiral) had again issued orders that we were to go 24/7 and take turns sleeping.

Along with the usual suspects of kayaks and monohulls, the starting beach had a different look this year. In 2007, a couple of proas (both of which, alas, sustained damage and did not finish) and a Hobie Cat 16 were the technological standouts of the fleet, along with winner Graham Byrnes EC 22 monohull (an enlargement of his successful Core Sound 17 and Core Sound 20 designs).

This year was different. There were a couple of Raptor outriggers entered, slender designs that featured a swing-down hydrofoil to promote stability when sailing with the ama on the windward size. World-famous multi-hull sailor Randy Smyth (FrontalLobotomy) brought a trimaran he had assembled out of “bits and pieces” in his yard. With the main hull around 20 feet long and about a foot wide and amas of a few feet long and a few inches wide, it had tear-drop shaped netting on each side for Smyth to perch when sailing. Its tall mast featured roller furling double headsails, and it looked fast just sitting on the beach. Besides that, Steve Lohmayer and Jamie Livingston (Lumpy and Bumpy) brought a Tornado, an Olympic class catamaran with the reputation of being the fastest beach catamaran in the world. Its mast, something like 31 feet tall, soared into the sky as some of us speculated how they would lower it to get under the bridge to Checkpoint 1 (they got it down just fine, thank you).

The Tornado catamaran, the winner in record time, and Matt Layden’s Sand Flea; a study in contrasts.

FLobotomy: An impressive boat which unfortunately had a breakage off Naples, which forced it out of the race.

Not quite as technologically awe inspiring but still fast looking was WaterTriber founder Steve Isaac’s Tridarka Raider trimaran. Heavier and bigger than the other high tech craft, it still looked (and would prove) a fast boat.

There were of course, an impressive array of monohulls, led by Graham Brynes’ (Roo) EC 22, the winner in 2007, and two of his Core Sound 20 designs, one featuring the father and son team of Paul and Alan Stewart (Dances with Sandy Bottom and SOS) and the other with EC veterans (and past winners in a Kruger canoe) Doug Cameron (Ridgegrunner) and Michael Collins (Greybeard). Matt Layden (Wizard) was back with is impressive 7 foot 11 inch Sand Flea, and there were a pair of Hobie Adventure Islands.

Starting day is always hectic. But unlike 2007 where small craft advisories were posted, this year we had only a moderate northeasterly wind. Nonetheless, there’s always a rush to get the food and gear loaded on the boat (because of marauding raccoons, you don’t leave such stuff onboard overnight, even though the boats are guarded. Since we didn’t have support crew with us this year, Noel drove the pickup and trailer to another, long term parking lot and then had to hoof it a mile back to the start, the promised shuttle not having arrived. Fifteen minutes before the 7 a.m. start, we were ready and went to the informal roll call. Then it was back to the boat and raising the sails.

Paddlers and sailors waiting for the 7 a.m. start at Ft. Desoto.

We didn’t actually hear the “Go” at the start, but figured it was time when the kayaks hit the water. We hung back a minute to let the kayaks start, and to make sure we didn’t interfere with Ridgerunner and Greybeard launching next to us. Our launch went smoothly, using a couple of eight-inch diameter fenders as rollers under Oaracle. Indeed, we almost had too much momentum when we hit the water!

Then it was off for the mouth of Tampa Bay. Last year, with strong northerly winds, Noel and I took the inside route down the ICW, and the winds funneled through the narrow parts of the waterway, keeping us moving. This year, with the moderate northeast winds and forecast (erroneously, it turned out) to shift to the east, we elected to go into the Gulf of Mexico and down the coast. That would avoid having the cross wind blocked by trees and buildings in the narrow parts of the ICW and also avoid the powerboat traffic. (Last year, the weather was nasty enough to keep most of them off the water for most of the day; not so this year).
Low tide had been around 1:30 a.m. and high tide wouldn’t be until around 7 p.m., so we had a light incoming tidal current opposing us and the moderate northeasterly wind. That set up a slight but not too unpleasant chop. We made steady, if somewhat slow, progress out of the bay, and I remember an impatience to get out, turn south and get a proper start to the race.

That turned out to take about an hour and a half as the winds became lighter. Once we made the turn to the SSE to head down Anna Maria Island, our speed was about 3 knots - and gradually declining.. Around 10 a.m., with the north end of the island clearly visible, Chief caught us in the Tridarka Raider. We had trouble maintaining two knots, but the powerful trimaran slide by us effortlessly, looking like it was making double our speed. We memorialized the passing by shooting mutual video clips.

Then we put up the jib, about 50 square feet, to try to squeeze a bit more from the win. But by the time Chief got about a half mile ahead, the slight wind died completely, and our sails hung limp. Not even Chief’s more able tri was moving.

I broke out our “oardles,” the rowing oars made from a castoff aluminum shaft double paddle, and began a relaxed pace.

Before long, we had caught and passed Chief, making around two knots. I remember around noon looking at the GPS, and its trip log was a bit over 10 nautical miles – in five hours. And most of that was in the first two hours. After about an hour and a half, the wind came back, not from northeast or east as forecast, but the northwest. Chief came sailing right by us again. Deja vu. We poled out the jib and ran wing and wing, to take the best advantage of the wind and then as the breeze built, took it down.

After the wind filled in from the northwest, Chief came zipping by us again in the Tridarka Raider.

Oracle’s rarely used jib came out in the light winds of Saturday morning and early afternoon. An extendable paddle serves at the whisker pole.

By the time we were off Sarasota – around 2 p.m. – we were making a good pace. The wind continued to build, probably to around 15, and the waves picked up to three feet or a bit more, enough that we began surfing. I was able to go in the cabin to get some rest (alas, no sleep) while Noel at the helm was doing a masterful job with Oaracle running as though she were on rails. The GPS had recorded a maximum surge at 9.3 knots. When I came back up, I shot a quick video clip of the conditions as Noel steered through a wave and hit 9.8 knots. A few minutes later (with the camera off), he hit 10.

We had a decision to make. Although progress was good now, the calm winds early meant we would not make Stump Pass before dark – and not before high tide had passed, which would mean facing an adverse current. Noel suggested going in at Venice Inlet, which we would reach with plenty of daylight left and before high tide. It was an eminently sensible suggestion which quickly became the plan. The only problem was as we neared shore, the seas would get a bit choppier and we would need to gybe to get into the east-west running inlet with the northwest wind. We got the gybe executed with only getting the tail of the mainsheet loosely wrapped around Noel’s neck – he didn’t even know it was there. How we did that, I still don’t know. Then as we approached the breakwaters, one slightly roguish wave tried to broach us. But I eased the sheet as Noel instantly corrected the course and Oaracle plunged on. I watched as the last two waves, now diminishing in size, shoved us between the inlet breakwaters and we casually waved at people watching us from both sides of the inlet. Noel glanced at the GPS as we entered and noted it read 8.9 knots; perhaps Oaracle’s most impressive harbor entrance to date. I took over the helm, giving Noel a well deserved break and he grabbed the camera to shoot a video as I narrated our exciting entrance. Notable is my broad grin, and Noel’s off camera narration of his novel way of hanging on for our wild entrance.

We quickly passed Snake Island, just inside the inlet, where several WaterTribers in kayaks were taking breaks. As we passed, Steven Bailey (Kneading Water) set out behind us, but for the moment couldn’t catch up as we passed under two bridges and headed down the high-banked canal south of the Venice Inlet. At first, we made excellent progress, but about halfway down the 6 mile or so stretch the wind began to lighten (and back to the northeast) and our speed slowed. Kneading Water caught up and chatted for a moment before he passed, imparting that Sandy Bottom and KiwiBird – companions from our Venice Canal passage the previous year – were slightly ahead of us, but we were unable to catch up in the slacking winds.

A pretty sight Saturday evening in the Venice Canal.

A spectacular sunset marked the end of daylight, followed by our most unpleasant incident of the trip.

It was an nasty reminder that not all of the challenges in an EC are found in nature. It was shortly after the sun when down when a 25 to 30 foot power boat, with flying bridge, approached from the opposite direction just before the end of the canal. Going a good clip, the boat slowed down as it approached, and then gunned its motor to full speed, throwing the largest wake possible at us. A bit actually slopped over Oaracle’s two-foot freeboard and into the cockpit as we heard the hoots and laughter of the teenagers running the boat receded in the opposite direction. A check later with other WaterTribers showed that this same boat deliberately “waked” other competitors in the channel behind us including at least one kayak that could have been swamped. Devise your own chosen revenge. Regrettably, that wasn’t the only such idiotic incident. KiwiBird, in her blog, related coming up to a powerboat waiting at a drawbridge and it’s helmsman locking eyes with her, and then backing into her before she could move, while claiming that since she was more maneuverable, she had to get out of the way. Fortunately, no damage was done.

The rest of the trip to Checkpoint 1 was uneventful. I rowed when the wind went light, but mostly it was a leisurely run down Lemon Bay and the canals and dodging the ferry that crosses the narrow channel just before Placida Harbor, at the northern end of Gasparilla Sound. We saw the swing bridge over the sound opening while we were still almost a mile away, and since it only opens every 15 minutes, decided to take down the main and mast and row in from the bridge. By the time we actually got to the bridge and had the mast down, 15 minutes had passed and it was opening for Jonathan Coble (RunningMouth) who was singlehanding a Sea Pearl and came in, I think, Gasparilla Pass (which I’ve never had the nerve to do). We passed under the swing bridge and then by the abandoned railroad bridge beyond, and then turned up the channel to head up the creek to CP1. RunningMouth had to anchor to get his masts down, while we continued to row, around a corner, under the fixed bridge, past the partially demolished RR bridge (featuring partly submerged, oyster encrusted pilings on one side of the creek!) and then to the checkpoint. We arrived around 1:30 a.m.

Turnaround took us an hour, during which we refilled the two one-gallon bottles of water we had consumed, visited the restroom, signed in and chatted briefly with other competitors at the checkpoint 1. To our surprise, we learned that Chief had experienced rudder problems and hadn’t made it in yet. I didn’t count, but the sign-in sheet showed we were well down the standings, which wasn’t surprising considering the calm and the light winds. I was somewhat surprised that more paddlers hadn’t made it to the checkpoint.

Around 2:30 a.m., we were off.

In about 45 minutes, we had rowed out into the sound, gotten the mast and mainsail up, and were proceeding down sound. The wind, which had been light to moderate, began to pick up, and also move more easterly. After about an hour, we paused to put a reef in the main, and then continued into Charlotte Harbor. In 2007, we had encountered some impressive waves that surfed us across. This year, the waves were smaller but it was still choppy as we bounced toward Pine Island Sound. It was also a bit eerie on a no-moon night to be sailing toward Cayo Costo island, past the impressive Boca Grande Inlet, and not be able to see anything of the inlet, which can be subject to strong tidal currents.

Noel went before for a rest. The GPS showed to the way as the channel wound its way around Cayo Costo, between some other islands, and then down Pine Island Sound. The drill was to use the GPS to get close to the unlit channel markers, and then use the spotlight to pick them out. There were, fortunately, no unpleasant surprises and the markers accurately corresponded with the electronic chart in the Garmin GPS. (It’s not pleasant to reflect in the wee hours of a dark morning that there are chart inaccuracies for Florida Bay.) There was also concern that the more easterly legs on this part of the course would require some tacking, but the wind stayed enough north to avoid that. With the first hints of a lightening sky in the east, Noel came up and I went down to rest. Although I had laid down a few times already, the combination of motion, adrenalin and excitement had precluded sleep. This time, I actually dropped off for an hour, and rested for another hour before coming up to find a sun low in the east sky.

Noel had reached the southern end of Pine Island Sound and pulling out the charts and conferring with the GPS, charted an easterly course skirting shallows and sandbanks to tack toward San Carlos Bay. He had already tacked through most of that tricky area, the wind now having gone ENE. The last fun part was identifying which part of the causeway connecting Captiva to the mainland. We could see where it should be, but couldn’t positively identify the correct span in the early morning light until we were fairly close. It was comforting to check the GPS chart. We squeezed close hauled under the wooden bumpers and headed east for the channel out into the open Gulf. The water at the mouth of the bay was a sloppy chop kicked up by the stiff breeze (we were still reefed), refracted off seawalls and churned by passing power boats.

Noel rests as Oaracle is hard on the wind after leaving San Carlos Bay.

Around 11:30 a.m., we were able to head SSE down the coast, now hard on the wind. The steep chop and uncomfortable motion continue as we departed the land. After a couple hours, I went below for some more rest, but found sleep impossible with Oaracle’s flat bottom pounding and slapping in the chop. The wind would ease and make us think about unreefing, but then pick up again. The direction was also a bit shifty, with Noel noting the hard-on-the-wind course varied from 120 to 180.

But Noel performed some more helming miracles and when I came up after an hour or so, he had managed to edge to within a half mile of the beach, which dampened the chop and actually made sailing pleasant. The wind lightened a bit and we shook out the reef and kept making fair progress. We passed a sailing and then powered cruise ships off Naples, waving lazily at the passengers. I hoped that the big furledsails.com signs we had on Oaracle’s sides were getting some publicity for Noel’s podcast site.

The sun set as we were off Marco Island, and Noel went below for some well-earned rest. As full dark descended, we passed Coxambas Inlet, on Marco’s south side and the abrupt dividing line between (overbuilt?) civilization and the Everglades. I had hoped to go in the inlet and then down Gullivan Bay to approach the Indian Pass entrance to Everglades City from the north. But with no light and an east wind blowing out the inlet, that wasn’t prudent, so Oaracle proceeded down the coast to Cape Romano. Approaching Cape Romano with its numerous and shifting shoals on a dark, moonless night was not my idea of an optimal situation, but we would be arriving at high tide. I debated calling Noel up, but there was nothing to see but the tip of the cape, so I let him sleep. As that passed, I hardened up as much as possible on the wind and on a course of 140 degrees proceeded past the cape, holding my breath. Nothing happened as Oaracle plowed on. After a half mile or so, I gambled on a short tack north, and then went back to 140. Noel came up, surprised we had rounded the cape (although the buildings on Marco were still clearly visible). I tried another tack to the north, but after a few minutes, the tip of the leeboard dragged on the sand bottom, and we tacked back and held course. The chart on the GPS soon indicated we had cleared the shoals, but we didn’t relax for several more minutes and we had traveled another mile or so and could be assured we were in deep water.

We now had been out more than 40 hours and I had had one real hour of sleep. Noel took the helm to begin what turned out to be a tedious beat to Indian Pass. I dropped off to sleep and an hour later was having a vivid dream about two authors and their publishing companies hawking books that continuous cacophonous noise was actually good for you. Then I woke up to a booming crash, followed by another one a few seconds later, and then a third, along with the feeling Oaracle had stopped. There was a gurgle as the boat picked up speed but then a few seconds later, there was another series of three crashing slams into the waves. Still tired, I tried to ignore the mayhem, but couldn’t get back to sleep. Eventually I went up into the cockpit to discover a frustrated Noel. He had set the GPS to read both course and velocity made good. The speed was nothing to brag about with the short waves bringing the boat to a near halt, but the VMG was about a knot or a little more – and that was the good tack. On the northerly tack, Noel observed a negative VMG. The motion and slamming seemed a little better when I was in the cockpit and we tiredly worked out what was happening. The high tide at Cape Romano meant we were undoubtedly bucking an ebb tide in the bay as well as beating in the wind. The short wave length was just the right length to give Oaracle fits. And finally, me being in the cabin changed the balance of the boat enough to aggravate the slamming. We swapped at the helm and Noel went below for some rest while I took a turn slugging it out with the elements. We also had to take extra care on a beat like this with one of us below. A common question from passers by about Oaracle was whether her asymmetry – mast and rudder offset to port and a single leeboard on the starboard side – makes any difference in performance and we always answer that it didn’t. But the mast on the port side meant that anyone lying down below necessarily was on the starboard side of the boat, which could be a problem when on port tack. We were able to get away with it this night because the wind was only moderate. But we made a point of keeping the sheet in hand on port tacks when one of us was below.

I made a long tack to the north, but wasn’t having much luck on improving on Noel’s VMG. But we continued to inch toward Indian Key Pass. In a way, the slow progress was tolerable because if we got there too soon, we would face the last of the ebb tide in the channel and likely have to wait for the incoming tide. After a couple hours we switched again and I went below to lie down, but not sleep in the bump and slap of our slow beat. I came up again just before sunrise and Noel proudly pointed to the now nearby green flasher narking the start of Indian Key Pass. It had taken us over eight hours to beat about 14 miles to the pass. But it was almost exactly low tide, which meant we should pick up the current on our way to Checkpoint 2 at Chokoloskee, south of Everglades City. We rounded the marker and headed up the first leg on a NNE course.

A couple miles ahead, where the channel jogs to the east, we saw the unmistakable sails of a cat ketch. The binoculars revealed it to be Ridgerunner and Greybeard on their Core Sound 20. We later learned they had experienced a beat just as hard as ours from Cape Romano (as had other competitors) and finding the tide turning against them, anchored for eight hours at the north end of Indian Key. We managed the first two sections of the channel under sail and with only a couple tacks. But the further we went, the more the mangroves blocked the wind and in the latter part most of the progress was under oars - probably more than an hour rowing in all. We finally emerged into the channel at the north end of Chokoloskee Bay, and saw the Core Sound almost across, ready to turn SE for Chokoloskee Island. We were finding the wind fluky and still needed the oars to make progress. And there was a reason for that flukiness. After blowing from the east as we entered Indian Key Channel, it was now shifting to the southeast. Or as Ridgerunner later put it, after making us beat and row our way into the channel, it was now going to rob us of a free reach to CP2 and instead make us beat again.
They were as the east end of the bay when they cut south into a narrow but fairly deep channel. We elected to cut out of the channel about half way across and angle toward the east side. I knew from past years that it’s inadvisable to beat down the west side of the bay, which is dotted with stakes and oyster bars. About a third of the way down the bay, we settled in behind Ridgerunner and Greybeard for the beat to CP2. To my amazement, we began to catch up, actually getting within a couple hundred yards at one point. But, as Ridgerunner later told us, he began working the centerboard, keeping it down in the shallow water as much as possible instead of leaving it mostly up. They began to pull away again. In a way we were lucky. It was now nearly high tide and there wasn’t enough water in the bay as we approached the checkpoint to have our leeboard fully down or get the centerboard in the Core Sound fully extended. Trying duplicate this beat at low tide didn’t bear thinking about.

Oaracle at CP2 in Chokoloskee; Ridgerunner’s Core Sound 20 is in the background.

Anyway, we landed around 11:30, a few minutes behind Greybeard and Ridgerunner (and about 12 hours behind our time from 2007, when we had strong tail winds). Dances with Sandy Bottom and SOS were just leaving in their Core Sound 20 as we sailed up. Mercifully, at near high tide the infamous Chokoloskee mud was not a problem. We signed in, bought extra water for the next leg at the convenience store. The tide was still an hour or so from high, so PaddleCarver, one of the shore crew drove Ridgerunner, Greybeard, Noel and me to a nearby restaurant for a belated breakfast. After more than two days of quickly gulped meals, it was a welcome break.

Back at the boats, we attended to a couple minor chores and then left as we had arrived, a few minutes behind Greybeard and Ridgerunner. We had planned to leave via Chokoloskee Pass, but saw the Core Sound heading out Rabbit Key Pass. We knew they were familiar with that route and elected to follow. We had a repeat of our entrance to Chokoloskee in that the wind had shifted again, so we were close hauled, except when the mangroves blocked the breeze and the oars were resorted to. There was almost as much rowing getting out as getting in.

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