The Sailing Vessel Pomaika'i
Fort Myers Beach Anchorage
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Port Charlotte to Fort Myers

Sitting here at the Fort Myers airport waiting for the flight back to Jacksonville (but via North Carolina for some absurd reason, Jacksonville is the redheaded step child of travel destinations) going over my simple “one day move” of the new sailboat from Port Charlotte to Fort Myers. This write up was supposed to be about sailing from Port Charlotte to Fort Myers but the weather made sailing a mistake for this trip.


The worst thing you can do with a sailboat is to make a schedule. One of the most challenging things about buying a project boat on a budget is that you’re on a schedule. The good deals are rarely where you’re living, so once you purchase the boat you need to move it to your location in the safest, most cost-effective means while working around employment obligations. With the boat located in Port Charlotte, I was left with two options to relocate it to Jacksonville.

The first was to work my way through the river system to Lake Okeechobee and then back out to the Atlantic ocean again via rivers and then up the coast to Jacksonville. This would me the fastest method but with the drought the water levels are low and there is one bridge the Pomaika’i can’t fit under. Plan B

The second is to sail down to Key West, then turn up the Straights of Florida and follow the coast up to Jacksonville to Miami. I was going to take a week to do this but give myself 9 days for unexpected weather  (sailing straight through it would be about 4  – 4 1/2 days). As part of the prep for this, I would go down to Port Charlotte and move the boat down to Fort Myers. My reasoning was: 1) The boat is located in a residential area in the back of Charlotte Bay so this would give me a full day to move the boat to a marina at Fort Myers that had a nearby outlet to the Gulf. 2) I could spend more time on the boat learning about the systems and checking everything out.

On this trip, I had hoped to sail on the outside from Port Charlotte to Fort Myers.


I arrived in Port Charlotte mid-Saturday morning. After a quick stop to pick up some simple provisions at the local Publix, I was soon on the boat. I had picked 12:30 pm as a departure time. The boat was located on a canal behind a private residence so leaving at 12:30 would put me on a rising tide in case I did run aground. It would take me about 40 minutes to make the trip from the house to the open bay. 

Other than a minor hiccup at the beginning, the trip out of the canal system was nice and uneventful. My current boat has the throttle and shifter on separate controls. Pomaikai has the those controls incorporated on one lever with a button to pull to lock it in neutral. This means your lever has 3 positions, pushing the lever forward makes it go forward and the further you push it the faster it goes. Same with reverse, with a neutral position in the middle. If you need to increase revs on the engine but not engage the transmission you pull a button out. 

Unfortunately, I forgot to disengage the neutral button as I left the dock. The wind started pushing me across the canal into the neighbor’s boat. No movement on the control lever had any effect on the propulsion of the boat (obviously). Luckily, I was able to figure out the issue and right everything before having to make a claim on my insurance. But with 2 strangers watching is was awkward.

Port Charlotte is a shallow bay. The shallowness makes for tight wave groups (short distance between) which makes the waves sharper. With the swell and winds pushing that swell directly into the bay it was a rough ride across. Motoring Pomaika’i directly into the wind and 2′ – 3′ waves was a wet ride. There is no dodger on the sailboat and it seemed like each wave sent water flying over the hole deck.

Moving into the main area of the bay, the swell and winds increased. Soon Polmaika’i was slamming down and through every third wave. At first, I did slow down to limit the action of the boat, but impatience with getting through the rough part I soon went back to charging hard. As I started to make my turn towards the inlet the swell picked up once again. And this is when the problems started.

All of sudden we were losing all headway against the current. At first, I thought that maybe we had run into a line or crab trap, but the engine still ran so that was eliminated (ask how I know about wrapping a line around your prop lol). Next, my thoughts were that I had lost the propeller. 

No problem. It’s a sailboat, we’ll just sail out to the ICW and get behind the shelter islands and deal with it. Between the current against me and the trying to sail directly upwind I could gain no ground towards the outlet or the ICW. You’ll see this on the track as circles in the middle of the bay.

At first, I thought maybe the current and wind were overpowering the engine and there might not be an issue. But, soon two sailboats passed me going out of the bay.

I decided to dive off the back of the boat and inspect the prop to see if I could find the issue. The current was so strong I had to hold onto the dive later, pull myself under by the rudder to inspect the propeller. The propeller was attached, was tight on the shaft and nothing was wrapped around the keel or propeller. I climbed back aboard, started the engine and then dove back down for a second inspection. The propeller was only turning with the current.

So now I realized I had broken something between the propeller shaft and the engine.


There is a great insurance program called BoatTowUS. For just under $200 they will tow you to port at no charge. Between buying project boats and my limited experience, this was a no-brainer purchase for me and I recommend it for anyone getting into boating.

Getting Towed

I decided at this point to call for a tow. I was tired from the trip down the night before and starting to make small errors in judgment. With the winds the way they were I couldn’t enter a marina under sail at my skill level.

Without the insurance, I would have sailed back into the the anchorages closer to Punta Gorda and anchored out for the night.

But the insurance would allow me to complete the mission (moving the boat to Fort Myers) and give me more options for repairs. Fort Myers has a number of haul-out yards and what seemed from my long-distance research more options for mechanics.

BoatTowUS showed up at my boat around 6:40 pm. We were soon attached by a tow bridle and started on our way to the ICW. Around 8: 30 that night the larger tow boat from Fort Myers showed up to take over. In the fading light and bouncing waves, we switched bridles and Pomaika’i continued on her journey.

The 5 hour trip down the ICW was a study in exposure and stamina. I had now been up for 41 hours (since I woke up for work on Friday at 4 am) with only a 2-hour nap in the Orlando bus station. Luckily the rain squalls that visited us all night (with me in the exposed cockpit) made it easy to stay awake.

We finally arrived at the Fort Myers marina at 3:00 am in the morning. The skillful tow guy, Ed, maneuvered the sailboat into the slip with minor assistance from myself. As we had switched to a side-by-side tie, this was outside my previous experiences.

My shower after another 2-hour nap was just about the best I’ve ever experienced.


I’ll start Monday off calling some local mechanics and yards to start diagnosing the problems and making action plans for repairs.

Hopefully, I’ll still be able to get on the water and start back to Jacksonville by next weekend. Otherwise, it will have to wait until the end of June.

If it was easy it wouldn’t be an adventure, and probably I wouldn’t be as interested in doing it. I learned a lot over the weekend, so still building that book of experience.


The time is off on this track for some reason. The total time was 12:30 pm until 3 am the next day, 14.5 hours.



Not many pictures as I was spending my time dealing with things. But I did a quick walk around the marina this morning and took some shots of Fort Myers Beach area.


Photos On Flikr

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