Windsong: The Journey Leg 2: Gulfport to Ft. Myers

The idea for the this leg was to go from Gulfport to Ft. Myers, then all the way to Stuart on the East coast via the Okeechobee waterway. My dad would help out for the offshore journey from Gulfport to Ft. Myers, and then it would just be Jenny and I for the week while she was on spring break. Unfortunately some bad weather made us have to stop our trip in Ft. Myers. This all took place March 6-7. I came back this previous weekend (March 20-22) to finish the trip across the Okeechobee waterway, and will post about that journey soon. Here are the photos to go along with the sail from Gulfport to Ft. Myers.

Leaving Gulfport. It was a chilly day.

Out of the inlet, sails finally up. We had to beat upwind to clear the inlet, which was a very uncomfortable way to start the day. Sizable short period wind swell pounding the hull. Once we cleared the inlet and turned Southwest things were comfortable.

Jenny and my dad cruisin

We headed out Southwest to clear the shoaling around Egmont Key. This made us have to cross the primary shipping channel coming into the bay. I was worried about what kind of traffic we would face, but only had to deal with this one cargo ship. Luckily it was going fast enough to pass a few miles away.

Ended up dead downwind once we cleared the shoals as we pointed South-southeast, our track for the remainder of the night. I poled out the jib for a wing to wing sail formation.

It was another great sunset, but I didn’t take too many pictures of it this time.

I trolled three fishing lines the entire night: a light tackle spinning reel, a 100 lb hand line, and a nice Penn conventional reel that came with the boat. Didn’t catch anything all night and in the morning I reeled them in only to discover a bunch of seaweed. The water was quite cold anyways, reports say not much was biting.

The night was mostly uneventful. I steered most of it with a bit of relief from my dad for a few hours. I was having a lot of fun on the wheel so I let them rest. The wind continued to decrease the entire night down to about 5 knots at the lowest. Overall we averaged about 5.5 knts the whole night dipping down to about 3.5 knots for a half hour. I feared we may need to crank the engine up if it didn’t pick up. Fortunately it did right when the sun came up and continued to pick up out of the Northeast to about 10-15knts. I made sure to reef before sundown this time, so we may have been a bit underpowered but at least the motion was better. Unfortunately my hack job at rigging the reef tore a patch on one of the reef points.


Everyone was awake around sunrise and we enjoyed the fresh breeze as it picked up a bit. I started to realize that when we rounded Sanibel Island that we would have to beat upwind to get to the channel for Ft. Myers beach. I’ve never sailed Windsong upwind so it got me a bit anxious. Once we turned I tightened up the sheets and we seemed to ride pretty easily about 45 degrees off, around 5.5 knots. As the sun continued to rise I was getting more and more tired, not looking forward to taking down sails and the nervy task of docking in a new place. We only had to reach Ft. Myers beach, which was right next to the inlet, but we weren’t looking to arrive until noonish.

As we were about two miles from the inlet, I got tired of thinking about it and just decided to deal with the sails. Unfortunately, I was never able to figure out what was wrong with my jib, it would not furl by pulling the furling line. At least I was able to roll it up by turning the drum by hand, and this time wasn’t nearly as much of a rodeo ride as the last trip. With all of the sails down we motored towards the inlet, straight upwind.

I had been worried about the quality of the fuel in the tank for sometime. The last sail down the coast surely churned up a ton of gunk in the tank, and the Rancor primary fuel filter was black and clogged afterwards. I changed the filter in Gulfport, but began to feel like it was going to become a continuous problem soon enough. Without fail, after motoring for a half hour or so the engine started to choke and loose RPMs. I knew for sure that it was the fuel filter, so I got to work changing it. Luckily we had two more spare filters and a portable diesel tank to fill the filter with. After changing the filter the motor cranked up and brought us in the inlet just fine.

Pulling into Ft. Myers Beach was not much of a problem. We had dropped off my dads car at Moss Marine the previous day, so I was able to scope out the approach beforehand. I came in a little fast when we docked and almost plowed into it, but reversed just in time. My dad had to drive all the way back to St. Augustine so he headed off after a bit. Jenny and I cleaned up the boat and ourselves and then went on a hunt for some food.

Turns out Ft. Myers Beach is a crowded spring break destination so people were everywhere. We wanted to nap on the beach after lunch, but the crowds made that close to impossible. I figured we would need more fuel filters if the tank kept acting up, so we looked up the public trolley schedule and found that it goes right to a West Marine. We got to the pick-up spot in time for the trolley, but as it rolled up it never slowed down and went right on by. Pissed as hell, it quickly dawned on us that we were on the wrong side of the road, but we figured the driver would have seen us as we were waving and yelling. I tried to call a cab, but I got the same story from all of them: too much traffic from beach goers to get anywhere within the hour, and West Marine closed soon. We gave up that search and I hoped that one last spare would last us at least until we stopped the next day.

The rest of the night was spent planning the next day’s route, fixing some soup on the boat and crashing early. We needed to leave early as someone reserved our slip the next day, so I figured we could have a short day and go roughly 17 nautical miles to downtown Ft. Myers, or if we are making good time all the way to LaBelle up the Okeechobee waterway.

The next day looked to be some great weather for my first full day of motoring Windsong. Here she is at the dock before we left:

Leaving Ft. Myers Beach

Right off the bat we had to go through a stretch known as the Miserable Mile. This is where the inlet channel markers turn into the Intercoastal waterway. When this happens, the red markers switch from being on the right to the left, vice versa for green thus confusing a lot of unprepared boaters. It also happens to be very narrow with less than a foot of water either side of the channel, makes a sharp turn and is crowded as hell. Luckily I had read about this and received some advice from a guy at the marina before we left. The worst part about it was the crowds, but all in all not too bad. Here is the Miserable Mile:

The next few hours were uneventful, but quite fun. It was a lot less stressful for a newbie boater to motor slowly surrounded by land than go offshore overnight.

We past downtown Ft. Myers around 1:00 pm and decided that we were good to go to further, possibly to anchor out at Franklin Lock up the river.

Here is the Ft. Myers Yacht Basin…this wont be our last time here.

Ft. Myers was lunchtime

About 3-4 miles out of Ft. Myers the engine started to choke up once again. Making the exact same sounds as it did the previous day. Great, I thought, right as we went past the last stop where I could have gotten fuel filters, I have to use our last one. I found a spot to anchor where the channel widened a bit further and I changed the filter to our last spare. After cranking the motor for a bit it seemed ok. I decided that we should turn back and stay the night at Ft. Myers so we could get some filters. But once we hauled the anchor and put it in gear, it choked once again. From the sound of it, I thought the fuel line from the tank was clogged with gunk. The engine just wasn’t getting fuel. I asked Jenny to let the anchor out once again, but while releasing the windlass her fingers got caught between the chain and the gypsy and cut them up pretty good. It was a scare, but once we were sure that nothing was broken we cleaned them up and she quickly felt better, though a little shaken.

While at anchor I decided it was a good time to take advantage of my $150/year towing insurance and called up TowboatU.S. for a lift back to Ft. Myers. While we waited a few hours for the captain to finish his current tow, we relaxed around the boat watching manatees pass. I even caught my first fish off the boat, though only a small catfish.

Anchored out:

Our tow guy:

We were towed into the Ft. Myers Yacht Basin where we would dock for the night. I got a reference for someone to come clean my fuel tank the next day, and set the appointment for first thing in the morning. Once we were settled in and showered, we wandered around town finding dinner and some groceries.

The next morning these guys came out to polish our fuel, pumping it through a few large filters and back into the tank. It was neat to see all of the gunk they were able to get out of the tank, repeatedly clogging their large filters until it ran clear.

The fuel polish machine:

We planned on trying to make it to Labelle that day, but as we monitored the weather it looked like we would only have another day of decent weather for the rest of the week. We would need at least three days to cross, and there was nowhere on the waterway cheaper to just leave the boat than the mooring field managed by the Ft. Myers Yacht Basin ($5.5o/day). I made the call to end the trip there and come back as soon as we could to cross the state.

Windsong at dock:

We stayed one more night in Ft. Myers then moored Windsong the next morning before we headed out and back up to Orlando.

Attached to the ball, triple lined:

The view as we paddled away:

Windsong from Hwy 41 leaving Ft. Myers:

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1 comment to Windsong: The Journey Leg 2: Gulfport to Ft. Myers

  • avatar


    I must be a couple of days ahead of you. We brought Saffanah from Ft Pierce (Harbortown Marina) to the Ortega river in Jacksonville this past week. We were forced to go the distance on the ICW – left Ft Pierce on Sat April 3 and put into Jacksonville on Wed afternoon

    Give me a cal if you want to discuss the trip – especially the Matanzas inlet sholing

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