Brian Takes His “Home Office” on the High Seas! – Days 16 -20

Brian Takes His “Home Office” on the High Seas! – Days 16 -20

Where we left off last week:

That night I spent another evening on the deck contemplating the stars, and enjoying the cool, salty night air before turning in. It was so relaxing to finally be at my destination, and be able to slow down and enjoy everything.

But Mother Nature had some surprises in store for me…

The morning after my hiking trip on the island, I awoke to a gorgeous sunrise. The water in the anchorage was calm AND glassy. I’ve always loved early mornings at anchor. It’s the most peaceful time of the day.

I decided to whip up a batch of pancakes, and ate them up on deck with my morning coffee. I checked the day’s weather forecast and it hadn’t changed. My phone’s weather app called for heavy winds throughout the next couple of days. There were small craft advisories already in effect. The winds were supposed to pick up within a few hours, and be blowing at a steady 18 – 20 mph with 30 mph gusts later in the day.

I had to get ready for it.

I didn’t spend much time lolly-gagging with breakfast. As nice of a morning as it was, I knew it wasn’t going to last long. So, I set about prepping my #2 anchor to deploy if things got too squirrelly. I then lashed down my mainsail. The cover was already on but I wanted a line wrapped around it just for extra protection to prevent it from flapping it around too much, and causing any damage.

The next chore was to get the engine running, and do a full check of it. This way, if I needed the engine later, there would be no question that it would start on the first try, and be able to run at high RPMs without any issues. Once I’d run the engine for about 15 minutes, and inspected all the belts, the water intake, the cooling system, shaft coupling and exhaust system, I then shut it down, and did a final check of the oil. Satisfied that my power plant was as fit as it could be, I tidied up the cabin, and settled in for a long stay on-board.

As a last precaution, I turned on my GPS chart-plotter, and started a track, which is basically a line drawn on the screen behind the icon that shows where the boat is. Normally, you would use this feature to save the path you took to get to a destination – a nice line that traces wherever your boat went. However, I was looking to maintain a “zig-zaggy” sort of scribble-blob right around my location icon. That would tell me that my boat was continuously swinging back and forth on its anchor, and not dragging. An elongated line drawn on the screen would be bad news. It would indicate that my boat was moving in a linear manner – blown backwards by the wind – and that the anchor was not holding. Dragging anchor is no fun, because inevitably, per Murphy’s Law, a vessel dragging its anchor will always drag toward water that is shallower than the given draft of the boat – or toward the nearest land mass.

I knew that, in 20 mph winds, my little inflatable dinghy with the electric trolling motor would be useless for getting around. The wind would blow me wherever it wanted and I’d be helpless to fight it. I was stuck on board until the heavy winds were over. So, once I was satisfied with the cabin, and made sure I’d left nothing on the deck to get blown away, I fired up my laptop, and got busy on BookLocker work. The boat was already rocking steadily and I could tell the winds were picking up.

Within just a couple of hours, the glassy waters in the anchorage had turned into 1-2 foot high whitecaps and the wind was starting to howl through my rigging. The ‘Molly was twisting and bucking in the waves as she tugged on the anchor line. I kept making visual checks of the land and the boats around me to make sure I was holding ground. In another couple of hours, it seemed that my visual landmarks were gradually shifting further and further upwind. A check of the GPS confirmed my fears. The zig-zag line that marked my boat’s pendulum motion on its anchor line was starting to lengthen – looking kind of like an EKG. I was dragging my anchor!

I scurried up to the bow, and tried to haul the main anchor in a bit so that the secondary would set not far from the primary’s location. However, all my strength was nothing against the wind and my 12,000 pound boat. It simply wouldn’t budge! So, I went back to the cockpit, got a spare block (pulley), and shackled it about halfway up the starboard toe-rail. Leaving the anchor line cleated in the middle where it was, I untied the end from the stainless steel ring in the anchor-locker that prevented all the line from escaping. I snaked the end back to the block I had set up, and ran it through. After pulling the rest of the hundred or so feet through the block, I then wrapped the line around one of the winches I use for my sail lines. After un-cleating the anchor line at the bow, I was then able to use the winch to slowly pull in the line, drawing the ‘Molly closer and closer to her anchor. Once I saw the swiveled end of the chain portion of the anchor line, I knew I was 30 feet away. I trudged back up to the bow to lower the second anchor.

Once the second anchor had touched ground, I went back to the cockpit to start letting the primary anchor back out. In another 10 minutes, I had two anchors firmly holding the bottom as the ‘Molly continued to jerk at her tethers. It was almost as if she was saying to me “The wind’s up!! Cut me loose and let’s sail!” Inland waters were forecast at 3-4 feet while the gulf waters were 6-7. That is not a pleasure cruise. So, I settled back in the cabin. I went back to work with a marathon of Humphrey Bogart movies I had on DVD playing in the background. The temperature had dropped down to the high 50s so lunch was comfort food – a grilled cheese sandwich and hot tomato soup.

And, so it went for two days. The winds died down considerably in the evening. But, I was still getting bounced around all night in the V-berth. It wasn’t the best sleep I’ve gotten aboard the boat. And, the next morning they picked right back up again. Occasionally, I’d go up on deck to have a look around. My clothing would flap wildly in the gusts like a skydiver’s jumpsuit. I took a few videos, but was consistently disappointed at how they failed to show the true magnitude of the gales.

On the evening of the second night, I studied the weather forecasts. The news wasn’t good. The next day was slated to be a little less windy. But, then the 20-30 mph winds were forecast to return again over the next 5 days. I checked in with Angela because she has a bird’s eye view of Tampa Bay. She told me she was seeing 3-4 foot swells and the bay was covered in whitecaps. In addition, she had gone to see her daughter earlier that day and the gulf was worse! There high-wind warnings on the Skyway bridge and 4-6 foot waves were breaking on the west side, spewing water and foam onto the rocks lining the southbound lanes of the highway. Offshore, conditions were far worse.

I had some thinking to do. Sitting on the boat for the next five days getting thrown around like I was a figurine in a snow-globe wasn’t why I took this trip. I wanted to do some more exploring on Cayo Costa, but trying to row my dinghy or motor across the anchorage with my little electric motor would have been a disaster. Not to mention, with the winds this strong, I wouldn’t be enjoying myself over constant concern over the ‘Molly dragging her anchor, and not being there to do anything about it. I didn’t want to travel any farther south. I simply hadn’t planned or budgeted for that. Sailing out in the gulf was just more risk than I was willing to take. Not with waves like that!

“Adventurous” as it had become, this trip was beginning to lose its “fun factor.” I decided it was about time to move again. I would spend the next day exploring some of the surrounding mangrove islands while the wind was more calm. I could then pack up the boat, and start early the next morning motoring up the Intracoastal Waterway (ICW). Having a fair amount of laundry to clean, and a serious desire to enjoy a good, restaurant-cooked meal, I decided to find a marina to pull into. I did some research, and found a small marina called Uncle Henry’s about fifteen miles to the North in Boca Grande. It would require me to turn off from the main ICW and head down a mile long channel that was extremely narrow. But, I’d have a chance to relax, and take a break from the rough-and-tumble anchor ride I had been on for the last several days. I went to sleep, happy that I had a plan to follow now.

The next day I spent the morning doing WritersWeekly work, then performed some boat tidying in preparation for the next day’s departure. Later in the afternoon, the winds had subsided considerably. So I grabbed my camera gear and glopped on the sunscreen, loaded up the dinghy, and headed out to the edges of the anchorage. The little electric motor pushed the inflatable silently and slowly through the water toward the mangrove islands. This is where having the electric outboard really pays off. There is an amazing variety of wildlife that inhabits the mangroves here in Florida. All types of insects and birds cling to the refuge of the thick tangles of branches above the water. In the treetops, ospreys can be found scanning the waters for their next target. Among the roots on dry land, fiddler and mangrove crabs can be found foraging and popping in and out of their burrows. In the shallows surrounding the islands, you can find blue herons,  snowy egrets, minnows, mullet, snook and shiners, stingrays, hermit crabs – the list goes on and on. Moving slowly and quietly is the best way to see as much of these creatures as possible because they tend to be skittish, and disappear at the slightest indication of a threat.

There weren’t many fish or crabs out and about but I got to see plenty of birds. And, to me, the mangrove trees are beautiful in and of themselves. I cruised around, in and out of little pockets of water that penetrated into the clumps of trees. I beached the dinghy, and strolled in the shallow waters for awhile. With my GoPro on the extended pole, I took some “stock footage” of my walking around the trees, and also got some video of my feet shuffling along underwater. I’m hoping to produce a full length video documenting my trip – “someday.” It was good to once again be of the boat, and wandering around in nature. I was happy.

Mangrove thickets are great places to hang out and explore.

Mangroves have vast root systems that contribute to the shallow water habitat and benefit lots of animals, giving them a place to hide as well as hunt.

Sorry the selfie looks like a selfie – but I was winging it. Note the beautiful mangrove with the long, stretching roots in the background.

Wandering the mangrove islands to see what critters I could find.


That evening I prepared a “special” dinner of hot dogs and baked beans. (I even cooked the hot dogs on ‘Molly’s outdoor grill!!) The temperature had dropped into the low 60s so my on deck shower was quick, unceremonious, and chilly – even with heated water. After some final late-night stowing and organizing, I turned in for the night.

The morning came way too early and I dragged myself out of the V-berth just as the sun was peeking over the horizon. The wind was calm and the waters smooth. I hauled up the anchor in fairly short order, and got underway. After a week’s worth of watching other boats come in and out of Pelican Pass, I was much more confident of being able to navigate the narrow band of deep water than I was on my first attempt. However, luckily for me, another sailboat was leaving at the same time as I was. I simply fell in behind them, and followed at a nice, safe distance. Now, if THAT sailboat were to run aground, I would know not to go that way!

Cruising alongside the long strip of beach, I noticed a beautiful bald eagle standing on the shore. My camera was down in the cabin and I struggled with the strong desire to run below and grab it to get a few shots for WritersWeekly readers. However, after calculating the math between what running aground would cost me versus missing a good photograph, I decided to stay at the helm, and finish getting through the pass in one piece. The eagle, not the least bit frightened by the sight of my sailboat gliding past him, just sat, and watched me go by. (As my luck tends to have it, if I’d run below and gotten the camera, he probably would have flown way.)

In another 10 minutes I was safely at Marker 74 and motoring north into the wind toward Uncle Henry’s Marina in Boca Grande.

Next Week – The long trip home : Winds, Currents and Shallows – Oh My!!


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

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

PART III: “Four Miles Out,” Cayo Costa, and DOLPHINS, DOLPHINS, DOLPHINS!!

PART IV: “Depth-Defying” Pelican Pass!



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.




Angela Hoy's popular online class is now available in book format!

Remember Your Past
Write It and Publish It
in as little as 12 weeks!

Angela Hoy's book will get you started!

  • Using Angela's MEMORY TRIGGERS, recall memories that have been dormant for years
  • Record those memories in chronological order in your memory notebook
  • Using the memory notebook as your outline, write your autobiography!
  • Also works for biographies and memoirs!

Read more here:

One Response to "Brian Takes His “Home Office” on the High Seas! – Days 16 -20"

  1. pamelaallegretto  April 29, 2017 at 1:40 pm

    Such an amazing adventure. It’s been fun tagging along for the ride without getting seasick, wet, or wind-blown.