For Capt. “Skipper” Bud, whose friendship I am eternally grateful for. 

Sailing Singlehanded…With Crew

A Tale of Two Captains, Two Very Different Boats & Going Around the Bend

By Kristoffer L. Stewart


A First Time
for Everything

In the fall of 2013, I finally had an opportunity to do what I’d dreamed of doing all my life: taking a voyage somewhere on a sailboat.

Sure, it was the promise of adventure on the ocean that initially attracted me to the idea. But more recently, I had been wanting to do it for a few other, more purposeful, reasons: 

I wanted to compare a traditional, monohull sailboat’s passage-making characteristics with those of a catamaran, to help me decide which would make the better boat to buy for my growing family.

And, I wanted to do it to help me accumulate the 360 days at sea required to obtain a charter boat captain’s license. For the purpose of owning and operating my own charter boat business some day in the near future.

In retrospect, I think a few lines from Charles Dickens’ classic novel,  A Tale of Two Cities, sums up my first voyage perfectly:

“It was the best of times, it was the worst of times.”

And paraphrasing the rest,

“It was wisdom…it was foolishness.

It was belief…it was incredulity.

It was light…it was darkness.

It was hope…it was despair.”

The Back Story 

This dream started 30 years earlier when my dad had bought a used 1985 San Juan 24 when I was about 10. Our family spent a few years learning to sail it (while trying to keep from running aground and out of the way of the weekend regatta boats) on Lake Ray Hubbard, near our hometown of Arlington, Texas.

In between trips to the lake, there was always a copy of Sail magazine and Cruising World laying around the house and I’d thumb through them sometimes, wondering what it would be like to cross an ocean on a sailboat.

And as often is the case, dad’s love of the sea, which was passed on to him by his Navy father, soon became my love, and his dreams slowly took root in me. Now, they are my obsession.

But my dad sold the San Juan when I was 12 and loaded us all in the family station wagon. We were leaving our dearly beloved relatives and everything I had ever known behind, for a new life in the Sunshine State.

I’m sure my dad fully intended to realize those dreams (or delusions?) by buying a 40-foot cruiser once in Florida and one day sailing it to the Keys; or better yet, maybe a catamaran like the ones we would see in glossy print ads for charter companies in the magazines. But it never happened.

Life just got in the way, as it so often does for the dreamer.

My parents’ combined income went toward keeping food on the table and a roof over our heads. Money wasn’t saved. A big, well-equipped cruiser was never budgeted for. Eventually the magazine subscriptions weren’t renewed. Dad’s dreams took a back seat to the tough reality of raising four young children.

But we kept the dream alive by attending the big in-water boat shows in Miami and St. Petersburg. And we were blown away by the cats we saw.

Bigger, better and more thoughtuflly-designed they seemed to become every year.

I’d see the catamaran charter company ads in those magazines and would succumb to endless daydreaming of what it would be like to enjoy that lifestyle full-time.

I used to wonder what kind of career path I could choose that would at least allow me to work aboard a catamaran.

Delivery skipper was one idea. Paid crew another.

But after college, I wound up taking a job with the very advertiser whose full-spread print ads always enticed me the most in the sailing magazines: The Catamaran Company.

I moved to Fort Lauderdale in 2010 to take a position as marketing assistant, getting paid now to attend the same boat shows I went to as a kid, and others, like the U.S. Sailboat show in Annapolis, and elsewhere.

During that time, I ate, drank and breathed catamarans (when I wasn’t asleep dreaming about them). Taking pictures of them, writing about them, interviewing their designers and owners, reading everything I could about them. Talking to delivery skippers. Visiting the big Cat Co charter base in Tortola. Test sailing nearly every popular make and model for articles I produced for MULITHULLS Magazine: Lagoon catamarans of all sizes, Leopards, the Seawind 1160, Maine Cat, and the Gemini 105Mc.

The Chance of a Lifetime

And then there I was one fine day, about three years later, now in my mid-thirties, that I found myself embarking on my first offshore passage. I would be crewing aboard a 37-foot monohull cruiser and setting off, as fate would have it, on my old man’s birthday, September 10.

I figured this was my chance to finally put to the test all of the ‘features and benefits’ sales & marketing hype of catamarans vs. monohulls that I had been hearing, reading and writing about for so long.

I’d be able to answer for myself the question: which makes a more comfortable, safer, better sailing boat offshore, in all kinds of conditions? The catamaran? Or the traditional monohull?

And, better still, I would be earning some time at sea to count toward the 360 days I needed for my captain’s license.

It was going to be perfect.

Or so I thought.

 Captain “Skipper” Bud

Skipper Bud knew about my love of sailing (and my obsession with catamarans) since I started joining him for daysails aboard his boat a few months earlier.

A few months before the voyage, my wife wanted to take me sailing for a birthday present. I told her we should look for a catamaran because she might enjoy it more since there would be no heeling over, less rocking in the waves and more space to stretch out.

We searched Google for: sailing Fort Myers catamaran

And found SAIL SWFL, and Skipper Bud.

Skipper takes up to six paying passengers out for coastal cruises and harbor sightseeing tours aboard his 35-foot Jeanneau/Lagoon “CCC” catamaran, Old Glory.

Learn More About SAIL SWFL

Skipper holds a U.S. Coast Guard issued license, the OUPV (operator of uninspected passenger vessel), commonly called the “6-pack captain’s license,” and runs a charter operation from Salty Sam’s Marina in Fort Myers beach, SAIL SWFL.

I give my dad the credit for introducing me to sailing on the lake in Texas, but it was Skipper Bud who taught me to sail. When I was just a little kid on my dad’s boat, I learned some, but mainly I just watched and tried to keep out of the way.

I never really understood why the sail at the front of the boat went from one side to the other whenever we turned to the left or right. And why the tall sail attached to the two big poles did not.

Before I could learn to truly appreciate any of it, dad sold the boat and moved to Florida.

Never to own a boat again.

From the Skipper I learned how to read the wind and how to orientate both the boat and the sails properly with respect to the apparent wind angle, along with how to steer the boat in rough seas, the art of sail trim, local knowledge of the water off Fort Myers Beach, and many other useful things for handling a big cat.

But perhaps most importantly of all that I learned from him, was an appreciation for true seamanship, which as writer John Rousmaniere defines in The Annapolis Book of Sailing and Seamanship is “both a technical discipline that one never stops mastering and a caring, alert state of mind we must never stop developing and improving.”

I have since learned that seamanship isn’t just about being a great sailor and knowing exactly how to set and trim your sails in any condition, or how to plot a course or find your current position on a chart; much more of it regards simply trying to be as safe at sea as possible by using sound judgement and proper planning, and having ample situational awareness at all times.

Skipper Bud was a commercial airline pilot for more than 30 years. To him, the safe operation of the aircraft or vessel is first and foremost. He takes this ethos with him every time he ventures offshore, even in the familiar near-coastal waters he calls home.  

Other boat captains, I would learn, are more concerned with maximizing performance

When I first met Skipper Bud, I was between full-time jobs, so I found myself with plenty of free time available to join him every chance I got.

I had been out with the Skipper on his catamaran about two dozen times when he mentioned someone he knew was looking for crew, and that it might be a good opportunity to get some additional sea time and experience.

I practically jumped at the chance.

Enter Skipper Bob “Cappy” Schwiner

Bob “Cappy” Schwiner on an open-water passage to the Keys, circa 1990.

When I first met Bob “Cappy” Schwiner and his wife Ann, I liked him immediately.

He was soft spoken, easy going, and showed that he at least had a good sense of humor.

His wife seemed like a great gal. They treated my wife Liz and I to lunch at a little diner near their home in Cape Coral, FL, so that everybody could get acquainted. We had a great time and I came away feeling very comfortable with them both.

So much for first impressions.

Initially, I had no concerns about joining a stranger on his boat for a few weeks. And I learned at lunch that it would only be me and him.

Cappy was planning to sail his 1980 37-foot Endeavor sloop, Time, from his home dock in Cape Coral, Florida, to Orange Beach, Alabama. There, he would meet up with his wife who’d be making the trip by car, to attend a big family wedding party taking place at a fancy seaside resort.

Skipper Bob is an accomplished, very experienced, even expert, sailor. Cappy told me that he had learned to sail from a very young age on the rivers and lakes of Kentucky. He had been a sailboat racer for decades, and also cruised some, too. 

Cappy had made more than a few passages of varying distances singlehanded (much to his wife’s consternation) and never suffered a serious, catastrophic incident of any kind in all those years. At least, none that he alluded to with me.

I would come to learn firsthand why his wife didn’t enjoy joining him. And why he mostly preferred to sail alone.

It’s a dangerous, risk-filled adventure sailing singlehanded.

Especially when you’re far enough offshore that help won’t or can’t arrive quickly if needed.

Although that certainly doesn’t stop people from doing it. Rather, much to the contrary, among the sailing culture it’s considered a true test of one’s skills and seamanship.

Indeed, more than a few sailors have circumnavigated the globe all by their lonesome. Men, women and even young teenagers have done it.

Even before it was widely accepted that to sail around the world alone could be done, people like the late Joshua Slocum were true trailblazers that threw the “what-ifs” to the wind and just did it. Forever immortalized in the long and legendary lore of sailing they became.

Cappy Aboard Sailboat with Family

Cappy and his young family, preparing to set sail, in 1984. 

Listening to him describe his sailing experience to me, gave him, in my mind, a sort of hero status that in reality he probably wasn’t fully deserving of.

Nevertheless, the perception that Cappy was the living, breathing embodiment of my childhood dream was there. And his skill as a sailor, to a landlubber like me, was therefore unquestionable.

I realized only after our voyage, that the blind faith I put in him and his experience, was probably a big mistake.

After lunch, Cappy and his wife invited us to their home where we would get a look at the boat and be able to discuss the voyage a little more while getting better acquainted.

Once we got there and went around back to the dock along the canal that ran behind their house, I was immediately impressed with the vessel I saw tied up there.

Time was an absolutely beautiful boat. To the untrained eye (in this case, mine), she seemed the quintessential Bristol-condition vessel. With her brightwork shining in the sun, every line neatly coiled and without even a spot of neglect or wear, she looked for all the world like a magical unicorn of ancient mythology with her mighty bowsprit jutting from her prow.

She lied there dockside so peacefully, so docile, and yet poised to take flight in an instant, her white sails like the wings of the mythical creature ready to carry me on her back to anywhere.

At 37 feet in length, she appeared perfectly capable of reaching virtually any navigable body of water on the planet.

Onboard were a VHF radio, solar panels, a rigid inflatable boat with an outboard motor hanging off the stern-mounted stainless steel davits, a diesel engine, a steering wheel, autopilot, radar, chartplotter/GPS, speed/depth/wind indicators, and a fully stocked galley of canned food and dry goods.

She was the boat of my dreams when I was that little boy on the lake in Texas; but the older I got, the more familiar and comfortable I became with catamarans. Somehow, having two hulls, two engines and more space to lounge around on deck and in the cockpit just makes sense to me.

I would have loved to have made this passage aboard Old Glory, Skipper Bud’s catamaran. Perhaps one day I yet will.

But even though Time wasn’t a catamaran, and I knew things could get mighty uncomfortable aboard a “leaner” (a derogatory term that catamaran owners apply to boats like Time with only one hull which lean over or “heel” sharply to one side when the wind comes up), I wasn’t about to pass up the chance to make this trip.

Cappy’s boat, Time, and Skipper Bud’s Old Glory are roughly the same length…but there’s no comparison to the beam (width) of both vessels. With Time being 11’7″ wide at her widest point amidships, Old Glory is an unbelievable 34% wider at 15.75 feet. 

More width = greater (initial) stability at sea, generally speaking, and so much more space to lounge around with. 

Illustration depicting exterior of the 35 foot Lagoon CCC catamaran (left) and the 37 foot Endeavor (right)

Cappy’s fishing rods adorning Time‘s stern arch

The Big Bend Passage

As I sat below deck in the salon, listening to Cappy describe the passage, I could hardly believe my luck. I decided that I wasn’t going to let life get in the way of seeing my dream become reality like my father had.

I was going to do it — my first voyage to a far-away land…albeit, Alabama, but it was perfect.

Our float plan — which I never saw in actual hardcopy document form (nor did I request it…which was probably another mistake of mine) — had us departing the dock behind Cappy’s house in Cape Coral, entering the Gulf of Mexico at Boca Grande Pass, heading NNW along the Southwest Florida coast, then more northerly toward the St. Petersburg/Tampa Bay area.

Just north of there, off of Tarpon Springs, we would be turning our bow to the northwest and heading offshore near Anclote Keys.

This was the famous Big Bend Passage, a well-trodden path that leads roughly to Carabelle, near Apalachicola, a path that many sailors are quite familiar with.

We would be taking the offshore route, staying well seaward of the coast. Our cellphones didn’t work out here, which meant there were days that I was out of touch with Ilse. And I didn’t know to warn her about this ahead of time, so, there were a few sleepless nights for her. 

Added to that, Cappy’s wife I would later learn had also expected to hear from us sooner it seemed. I attribute our delay to an drive shaft issue and a becalming we suffered…to be described later.

Using Google Maps, I calculated a rough measurement of the total distance, dock-to-dock, from Cappy’s home to Perdido Pass…485 statue miles = 421 nautical miles.

The landing point of our first outward bound crossing was to be Dog Island. From there, we’d make our way East to Apalachicola and up the river that shares the city’s name, heading across small Lake Wimico located in Gulf County, FL, then down a man-made canal, before re-entering the Gulf of Mexico at Port St. Joe, FL.

Back in the Gulf, another open-water, offshore passage awaited that would take us to our final destination near Orange Beach, Alabama.

None of the itinerary was discussed during our meeting, however. I just figured Cappy knew where he was going and how to get there. I was so green with inexperience that I just didn’t know to ask about the particulars of our route.

To me, it just sounded like a great adventure and I’ll I’d have to do was enjoy the ride. And maybe I’d be able to learn a thing or two about sailing, piloting and seamanship along the way.

It would be my ‘job’ to make sure nothing happened to Cappy. Although if some unforeseen, tragic fate had befallen our skipper, like a serious injury or medial emergency, or to the boat, such as a catastrophic incident like a collision with another vessel or major mechanical mishap, I wasn’t sure what help (if any) I would actually be.

There inside Time’s comfortable main cabin, Cappy told me he’d made this same passage several times before. Both with crew and without. He also said that he had personally ripped out and worked on every single one of the ship’s systems at some point or another and literally knew her inside and out.

So, I reasoned, he was a good sailor and mechanically inclined to repair virtually anything that might fail along the way. This gave a mental sigh of relief to my wife I’m sure, and a big vote of confidence for him in my mind.

Clearly he knew what he was doing. The boat seemed in great shape. And from what he told me, he didn’t expect much more from his completely green crew member than moral support.

In hindsight, that was probably another mistake that I made, before we even left his dock: failure to adequately and clearly establish expectations.

We talked a little more about the passage aboard Time before making for the pool patio where we enjoyed a couple of cold ones and the conversation turned to Cappy’s love of fishing. He even gave me a prized lure that he swore was irresistible to most of the fish in our area. I came to find out that he often fished the many canals and narrow channels of Cape Coral from his outboard motor-powered dingy.

If my wife had any trepidation about my leaving her for several weeks to join a total stranger aboard a sailboat neither of us had ever personally been aboard and sailing beyond sight of land, she didn’t show it.

I think she knew how much it meant to me. What a extraordinary opportunity it was to learn from a seasoned sailor and to gain a few weeks at sea counting toward the 360 total days I’d need for my captain’s license.

Still, it was the first time of any real length that we’d be apart since we met, so when we said our goodbyes a few days later, I’m sure she secretly worried about what could go wrong out there.

Alone on the Gulf.

In the dark.

And beyond cellphone reception range at times.

Of course she had questions for me later: When exactly did we expect to arrive at our final destination? How long would we be there? How far offshore would we go? Would we be able to contact someone if we need help? When we would leave for home? When exactly did we expect to return to Cappy’s dock?

All questions that I probably should have been asking myself, I realized later.

Because I didn’t know the answers to any of them.

Any sailor will tell you that a prudent seaman will always have a plan in place and an itinerary, the Float Plan…but it’s Mother Nature and the ‘cruising gods’ that actually determine your fate.

And likewise, plenty of well-seasoned sailors will tell you that the ship’s captain himself can have a considerable influence on the outcome of any voyage. A lesson I was soon to learn for myself.

But I was elated to finally be going on an offshore coastal passage aboard a sailboat, and after my wife and I drove home from our meeting, I began considering what I might need to take along with me.

Day 1: Cape Coral to Tampa Bay

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By | 2018-01-09T08:48:41+00:00 November 30th, 2017|Latest Articles|