Brian Takes His “Home Office” on the High Seas! – Day 11

Brian Takes His “Home Office” on the High Seas! – Day 11

“Four Miles Out”

On Monday, March 27th, I arose before sun-up. I took advantage of the last opportunity I was going to get to take a landside shower for awhile, and then dis-connected the Floggin’ Molly from all the luxuries and conveniences (free-flowing electricity and water) of dockside life, and motored over the short distance to the fuel dock at the Crow’s Nest Marina to get my holding tank pumped out. (For those who don’t know what a “holding tank” is – it’s where everything you flush down a marine toilet goes.) Asking the dockmaster about my chances of getting a slip on my return trip home, he warned me that this was their busy season, and that I would want to make a reservation. Apparently I had gotten really lucky when I blew into town four days earlier, and they actually had this dock space available upon my arrival. So, I booked a slip for the 12th of April to ensure I have a safe place to stay after a full day of sailing. I then departed and was motoring through the inlet at 7 a.m.

Farewell, Venice!

Shortly after clearing the jetties, I turned the Molly’s nose into the wind and started getting the mainsail up. Today’s sailboats have electric winches and mainsails that roll up into their masts, making the act of getting your sails “up” simply a matter of pushing a button. I have yet to be able to justify such expenses. So, I still raise my mainsail the old-fashioned way – with the halyard (a rope that pulls up the sail) wrapped several times around a winch and manually cranking a winch handle to raise the sail, inch by inch, up all 54 feet of my mast. So, for me, raising the mainsail is still sort of a special moment – even a ritual. It’s five minutes of grueling physical work that is a prelude to the moment you can shut off the noisy diesel engine, and adjust into the new sensation of being aboard a boat that is silently gliding through the water – the only sound being water rushing under the hull.

Once I had the engine off, and had pointed in my desired direction, I unfurled the jib (the sail at the front of the boat) with a good tug at her line. My jib is on a roller furler, kind of like a spool, so as soon as the wind catches that sail, it unwinds itself, and pops open as it catches the air. Then, I just haul the line in to trim the sail.

Sails Up!!

Once the sails were set, I settled in for my slow, casual journey. I continued due west into the horizon for a little bit until I knew I’d have enough water under my keel, then turned slightly south. Due to the forecasted wind directions and the curvature of the land mass prior to my approach to Boca Grande, my final destination, I needed to be about four miles offshore to avoid having to make more pronounced steering corrections later on in my trip. I wanted to avoid any unnecessary tacking, as this was a 35 mile trip and I already knew it would take me most of the day.

Entering Boca Grande requires going 4 miles out

The key to it all was that I needed to be anchored before sundown. Here’s why:
The anchorage I wanted to stay in, called Pelican Bay, is just on the East side of the Cayo Costa State Sark. It’s an island, unreachable by car and very scenic. The entrance to Pelican bay is bordered by shallow areas. All nautical charts will show that to get to the seven and eight foot deep anchorage, one has to cross over a zone that is only four feet deep. Now, four feet is no problem for pontoon boats, flats boats, small recreational cruisers, and even some of the larger recreational trawlers. However, for larger sailboats, this presents a problem. A lot of sailboats larger than 30 feet have a keel that extends their draft to 5, 6, and 7 feet – all depending on design. Trying to cross a four foot area would pretty much guarantee a grounding.

However, Pelican Bay is one of those areas where you have to throw away the charts and go by local knowledge. There is actually a five to seven foot deep “channel” that runs across that four foot area, along a beach, and allows you to then get into the deeper anchorage. The only problem is that this “channel” is not marked. This is not a part of the Intracoastal Waterway, which is maintained by the US Army Corps of Engineers. And, the state of Florida apparently has determined there is no benefit to mark this path, nor note it in nautical charts. Therefore, you have to listen to those who have gone through the channel before. For illustration purposes, I took a screen shot from my Navionics chart to show this course.

The unmarked “channel” at Pelican Bay.

The instructions go something like this:
From ICW marker “74”, you turn West toward the beach on Pelican Point and locate a sign that is posted in the water. (This is a sign warning boaters that the area is an idle speed zone.) Motor toward that sign until you almost hit the beach, then veer to the left about 15 yards off the beach. Then travel the length of the beach until just about where the sandbar ends, then turn left into the deep anchorage.

Suffice to say, this was not something I wanted to try for the first time at night.

It was a nice, cool day and the wind was with me only it wasn’t as strong as the forecasts promised. However, I relaxed and enjoyed watching the sun rising higher and higher over the shoreline. At four miles, you can still see the shore and the buildings. But, people are non-existent without binoculars. Everything seems so peaceful at that distance. There were still no other boats out that far that early so just about everywhere I looked was wide open water. I relished the seclusion.
As the day unfolded, I alternated between sailing and motor-sailing to ensure I was making acceptable time. The steering was mostly being done by my autopilot. And, this would have made the whole day far more relaxing if not for one thing – crab traps.

Having grown up in a coastal town in Florida, I’m used to seeing the little round Styrofoam balls that mark crab traps floating all over the inland waterways. There are thousands scattered all throughout Tampa Bay, my home cruising ground. Connected to each of those balls (only about six inches in diameter) is a length of rope that extends all the way to the bottom and connects to a steel framed, chickenwire box made to catch blue or stone crabs. Having a propeller come in contact with one of those ropes can cause a major delay in one’s day as it requires diving below the boat to cut the line free that will have wound tightly around the prop shaft before stopping the engine. I was amazed to find these so far offshore. But, here they were, one string of bouys after another, each stretching about a half mile or so. Unfortunately for me, this meant that instead of letting the autopilot do its job, and then relaxing in the cockpit to read a good book, or write of my adventures on the high seas with an occasional peek over the deck to avoid any calamities, I wound up instead having to keep constant watch ahead of the bow, and changing the autopilot’s course each time one of these little nuisances came into view. It was like navigating a mine field. I strained my eyes ahead of the boat – nothing, nothing, nothing, then suddenly I’d see another tiny white dot bobbing ahead. Then another, and another, and another. I had to figure out which way the strings were running so that dodging one mine didn’t simply put me on a collision course with the next.

And, so the day went, alternating back and forth from “purist” sailing to motor sailing, keeping a close watch for crab traps, and enjoying the serenity of seclusion. Occasionally, a powerboat would go by but they were always about a mile away from me. I couldn’t even hear their engines. I was alone in the world I’ve been dying to get back to for years.

Times like this give one ample opportunity for reflection. You know – all the “ifs” and “hows” and “whys.” I try to avoid “wouldas,” “couldas,” and “shouldas.” Those rarely do any good. But, I do like to take a personal inventory, and ask myself if I’m happy and, if not, what I am going to do about it. And, honestly, I realized that, indeed, I’m the happiest I’ve been in a long, long time. I had a big dream of living on a boat and now I’m here. I overcame challenge after challenge and I’m still going strong after six years. I work a great job with lots of rewards and I work for awesome people for whom I’m not just a number, or a line item on a personnel roster. How many people in America can say that? I think I have realized the satisfaction that successful freelance writers enjoy. Ten years ago, I had dreams of being in such a place as this – but I really had no idea how I’d get here.

About five hours into the trip, I saw a shrimp boat out on the horizon. These things are massive! It had its outriggers fully extended with nets hanging off of them. It looked more like a large plane flying just over the surface of the water than a boat. Again, I let myself fantasize about what it must be like to work on a large fishing vessel. But, I came to the conclusion that it must be hard, tiring, and smelly – unlike what I was experiencing aboard the Molly out here in the endless blue expanse. True as it may be that there are many, many boat owners in America and the rest of the world – when you look at it as a percentage of the entire population, very few people get to have experiences like this – the contentment, the freedom. It’s taken me awhile but I’ve gotten to a really wonderful place in my life.

Another couple of hours later, I actually came within a few hundred yards from one of these monster vessels. It was actually anchored out there in 30 feet of water. “How odd,” I thought as I studied it through my binoculars. I saw no one on deck, save for about a hundred seagulls all sitting on the rigging. The nets were on the outriggers but no one was working with them. It was almost as if the boat was abandoned. But, as I thought some more about it, I realized that the best shrimping is done at night. I remember as a young boy, friends of mine would take me to a bridge in Sebastian that had a catwalk just a few feet above the surface if the Indian River. We’d lower Coleman lanterns down on chains to just inches above the water, and sit there with nets on long, long poles. Every few seconds we’d see the glowing eyes of shrimp floating just under the surface, and quickly scoop them up in the net. On good nights, we could fill a couple of five-gallon buckets with shrimp in a couple of hours. I assumed that the crewmen were all in their bunks getting the rest they’d need for a long night of running, and hauling up nets.

Shrimp Boat

As I continued to study the rusty old giant, I noticed dolphins constantly surfacing all around the bow and the anchor chain. I absolutely love watching dolphins and I couldn’t help but smile and laugh a little at the sight of the fins gracefully breaking the surface as puffs of wet air shot from their blowholes. So beautiful these creatures are. But, they were still too far away to get a picture! I cursed my luck, realizing that the mischievous creatures had once again foiled my plans to capture some good photos to share with you readers.

I continued to sail on, leaving the mystery hulk vessel behind as the playful dolphins persisted in taunting me with their fins and tails.

The markers of Boca Grande

At about 3 p.m., the first buoys marking the entrance to the pass at Boca Grande came into view. The end of my journey was nigh! And, I was elated to know that, within a few more hours, I’d be peacefully swinging from my anchor, and could rest my eyes and mind under the stars with some hot food to help me wind down. By 3:30 p.m., I was passing the giant, bobbing steel cans. The wind was blowing into the channel from the West so I started the engine, and turned the Molly away and into the wind to bring the sails in. The channel was wide and deep but, as a rule, I never try to sail into a channel I’m not familiar with. There are just too many things that can go wrong in unfamiliar ground and I want the ability to stop and back up, or change course without the worry of changing sail position. So, with the bow pointed due West, and heading back out into the Gulf, I released the main halyard, and stepped out of the cockpit to help pull down the sail. (My mainsail does not just fall down all on its own. It requires someone on deck to tug it down after it collapses about halfway.) As I was working my way forward, something caught my eye off to port. I looked, and saw nothing, but kept scanning the blue-green depths. I knew that something had been there. Then, suddenly, a form penetrated the darkness and leveled out just under the surface, and shot under my boat….then another.


I scurried back into the cockpit, and grabbed the GoPro camera. As I emerged again – there they were! Three, four, FIVE – an entire pod!! Again, off to port, they angled over, and rocketed back under the boat to starboard. I scampered across the deck, almost clobbered myself ducking under the boom, and ran along the toe-rail to the bow. They were still there! Just under the surface – surfing my wake! With video running, I kept the camera aimed at the gorgeous sight of now SIX dolphins surfing and playing across my bow. I became elated! I’m not sure what caused me more joy – getting to watch these majestic creatures in full view, or the fact that they finally let me film them!


After about 30 seconds of video, I wanted to get some still shots on my phone so that I could immediately send them to friends and family. I ran back to the cockpit, grabbed my phone, and bounded back up to the bow. But, they were gone. No sign at all of my new friends who had come to show off for me. I was a little sad, wondering if my boat hadn’t been fast enough to give them a good thrill ride or if they had actually noticed I had disappeared and decided there was no further reason to stick around. But, for whatever reason, they were gone, and it had only taken a few seconds of my absence for them to lose interest. I went to the mast and finished pulling down the sail – my heart still racing from the incredible experience I’d just had. Without a doubt it had been THE high point of the entire day! The full video can be seen on my new YouTube channel HERE.

The mainsail wound up getting stuck on one of my lazy-jacks and I had to pull it back up to cajole it back into place, clear the lazy-jack, and get the sail all the way down. I turned the Molly back to the East and realized that I’d put another half mile or so between me and the channel markers. I throttled up to head into the channel and began to mentally prepare myself for what was to come in another hour or so … my nerve-racking entry into Pelican Bay…


PART I: An emergency U-turn just in time to avoid running aground!

PART II: Hair raising anchor antics and the journey south!

PART IV: “Depth-Defying” Pelican Bay, Hiking in Cayo, Dolphin Chasing Dinghy…



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Brian Whiddon is the Managing Editor of and the Operations Manager at An Army vet and former police officer, Brian is the author of Blue Lives Matter: The Heart behind the Badge. He's an avid sailor, having lived and worked aboard his 36-foot sailboat, the “Floggin’ Molly” for 9 years after finding her abandoned in a boat yard and re-building her himself. Now, in northern Georgia, when not working on WritersWeekly and BookLocker, he divides his off-time between hiking, hunting, and farming.


Fall 2023 24 Hour Short Story Contest

10 Responses to "Brian Takes His “Home Office” on the High Seas! – Day 11"

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  6. Gene Parola  April 5, 2017 at 4:47 pm

    Always good to get a modern sailing yarn. Don’t know why publishers are stuck on 16th century galleons and their unlucky crews. Check out “The Devil to Pay” (and the source of that nautical title) at

    • brian  April 5, 2017 at 6:02 pm

      I agree, Gene. I enjoy a good read about the early traditional sailing. But I really love what I’ve got here and enjoy sharing it with others.

      The biggest message I like people to get from my stories is that I’m a normal guy getting to experience all this amazing stuff. I used to devour stories told by cruisers who’d sailed off to distant exotic lands and had incredible experiences. But then I’d read “About the Author” and it would say “So and so is a retired electrical engineer / brain surgeon / stock broker / nuclear physicist…etc, etc – and would always get disheartened, because I couldn’t find the story of the everyday guy making an regular middle class wage who got to go do this stuff without breaking out hundreds of thousands of dollars.

      With today’s boats and technology, these dreams are closer to being reality for more people than ever before!
      Glad you enjoyed the read.


  7. pamelaallegretto  April 5, 2017 at 2:40 pm

    I second mctag2015 and add another wow!

  8. mctag2015  April 5, 2017 at 10:41 am

    Wow. Just wow. And now…on to the video.

    • brian  April 5, 2017 at 5:49 pm

      Thanks mctag2015. The video is AWESOME (being there was better 🙂 ) Hope you enjoy it!!