I pulled an owner’s prerogative when Gary took his turn below and let him sleep on while the coast slipped by on the pleasant but cool night. The sailing was so enjoyable that I shut off the GPS light to avoid that electronic distraction.
I set a modest task to accomplish each hour to help stay alert: use the pee bucket or shoot a selfie with the waterproof camera. Periodic horizon scans showed no other boats near us. It was just wind, sail, sheet, stars, tiller, and moon.
Toward dawn, off Naples, I roused Gary and we enjoyed a spectacular sunrise with the reds and yellow playing off an exploding cloud before I went below for a couple hours sleep. When I came up, the wind has freshened a bit and conditions were lively as we approached Marco Island; Oaracle was averaging 5.5 knots. Around 10 am, we passed Marco Island and Caxambas Pass and came hard on the wind on a course for Cape Romano. Although we were only about a half mile off the coast and the winds were well managed with the double reef and the waves were not high, the seas were extremely choppy and sloppy and apparently exactly the wrong distance apart for Oaracle. Again and again the boat slammed down off the waves and for one of the few times in her career, I was concerned about doing serious damage. I could not imagine taking this kind of pounding for the five miles to Cape Romano. Gary suggested tacking close to the shore to see if we could find calmer water. We closed the beach about 100 yards from the south side of Caxambas and decided to take a break on shore, and I recalled Doug Cameron (Ridgerunner) telling me the south side of the pass was sailable. As if to prove the point, an old Stiletto catamaran came motoring out of the pass and anchored nearby, disgorging a half dozen people who scoured the beach for shells. While I held the boat off the extreme shallows next to the beach, Gary scouted around the point and talked to the skipper of the Stiletto who assured us we would be able to sail up the pass. So we reached north around the point and headed in. Although we sometimes were reduced to half the leeboard, we did indeed manage to sail in Caxambas, which proved to be a lovely route, if somewhat slow as we were bucking an outgoing tide.
Eventually, we rounded Helen Key and entered Gullivan Bay from the north, the first time in an EC I had not taken the route past Cape Romano. A couple of tacks brought us around some shoals and Coon Key Light where we could begin beating to Indian Key Pass.
Conditions were still rough, but much more manageable. We spent the rest of the afternoon beating, with the spray flying, to Indian Key, arriving about an hour after dark and facing an an outgoing tide that discouraged us from trying to beat in that night. Instead, we sailed to the north end of Indian Key and then crossed the channel to a deep bay on the north side between some mangrove islands that gave us protection from the strong easterly winds. If we left at dawn, we would catch the middle of the incoming tide.
We anchored at 9:20, had a meal, tidied the boat as best we could, and went to bed. At 6:30 am on Tuesday, we were up and getting ready to go and by 7:15, Oaracle was underway. The wind was light, but we left a reef in the sail because it was predicted to get stronger (and did). The easterly direction meant that the mangroves lining Indian Key Pass did not block the wind and we efficiently beat up the channel, bumping the leeboard only a couple of times. With the tidal boost, which gave us tacking angles to brag about for the rest of our lives, in a mere 80 minutes (something else to boast about) we were at the north end of shallow Chokoloskee Bay.
Things got interesting here. The wind had indeed picked up and we had to short tack up the channel towards Everglades City before heading southeast, with long and short tacks, to Chokoloskee Island and checkpoint 2. The GPS shows we made steady progress at 4 to 5 knots and occasionally higher. I felt comfortable with the reefed sail, but we were passed by Sirtackalot and Kokopedal on a Sea Pearl carrying full sail. Anyway, about an hour and 45 minutes after reaching the bay, we gratefully made the checkpoint.
At this point, we were 90 percent sure our 2017 Everglades Challenge would end here. The main reason is we had caught a forecast on the marine radio the day before which foretold east to southeast winds of 20 to 25 knots for the next stretch down the Everglades coast. Easterly winds were predicted to be even stronger between Flamingo and Key Largo, with gusts along the last stretch hitting 35 knots. We had been unable to get a more up-to-date forecast. After fearing the boat would be shaken to pieces if we had continued to beat from Marco to Cape Romano, it seemed imprudent to risk getting caught in the wrong kind of waves off the Everglades Coast or going around Florida Bay.
Minor factors were we had equipment/gear failures. Shortly after the start, I had stumbled when installing the foam boot around the mast where it goes through the hatch covering Oaracle’s cabin slot. The collar broke in two and half went overboard, leaving no immediate and effective way to prevent the mostly nonstop spray from getting in the hatch slot around the mast. I stuffed scraps of foam and pool noodles into the opening, but it as a poor substitute. At the stop at Picnic Island, a makeshift mast boot of duct tape was made, which was marginally better.