A Million Miles At Sea: Ups and Downs of Sailing The Florida Keys (Part 1)

A Million Miles At Sea: Ups and Downs of Sailing The Florida Keys (Part 1)

The vision: “The stars at sea are unlike anything you’ve ever experienced.  180 degrees of complete illumination, hundreds of specks of light you never knew existed if you’ve only looked at the sky near cities.  And night sails are the best way to experience it… the winds are steady, the seas are calm, all you need to do is put the boat on autopilot and enjoy the view from the foredeck.”

The reality: “You know what to do if one of us goes overboard, right?  You know where the ropes are?  You know how to press “man overboard” on the GPS?  First, you need to try to save me yourself, then you radio for help.  You know where the whistle is on the life jacket?  You’ll have to whistle like hell because the reality of the situation is, with the boat rocking like this, no light from the moon, the rain, there’s a very slight chance, I’ll even be able to see you out there”, Brandon hollers over the sounds of the gusting winds, clanking of the sails and crashing of the waves.  I grimace in a failed attempt to fake a confident smile and not puke, peering out of a crack in the cabin door where I have been placed to shout GPS directions since the torrential rains made it impossible to keep the tablet outdoors.  Brandon is decked out in the stereotypical sea captain yellow rubber overalls and headlamp, chained to the base of the wheel and has just given up trying to fight the sea.  We both hope that heading 270 degrees west won’t send us into any wrecks or rocks since that’s the only direction the boat will go.  In the cabin, my panicked thoughts race between praying that Brandon doesn’t get thrown overboard, trying to hold down my backpacker-bean-dinner and reprimanding my naivety for getting on a sailboat without realizing it could be the death of me.  Brandon calls me on deck to steer for a bit to relieve himself, realizes we’ve been dragging a crab trap for the past three hours and shouts over the wind, comes up with a  plan to remove it so we can move the wheel again.  He dangles over the edge, waving the gaff hook in the darkness to unhook the contraption.  He lets out a victorious yelp as we leave some of the trap behind, I feel the wheel get a little freer and tried to wiggle more strategically through the wild waves.  Apparently, I had been forgetting to breathe, release a huff of air and surprised myself with a weird sense of peace about the situation because despite all the chaos, he had a plan and I knew we were going to be ok.

He takes over the wheel and I lie on the bench to calm my nausea, convinced that I would be too nervous and gripping on to the side of the boat too tight to sleep.  However,  at some point, I fall asleep on the bench, hanging on to side cabinet for dear life, and am surprised when the sunlight wakes me to significantly calmer seas.  A bit confused to awaken in such relaxed surroundings, I squint and see Brandon whistling to himself, relaxed behind the wheel.  “Good morning, sunshine” he greets me.  If our life belongings weren’t scattered around the floor of the cabin below and deck of the boat still damp, I’d barely believe what just happened.  Still overwhelmed, I give thanks that I was still alive, albeit a bit wary for another day at sea.

Beautiful sunset at sea

Beautiful sunset at sea… similar to the sight I woke up to

“The difference between a fairy tale and a sea tale? A fairy tale starts with ‘Once upon a time’. A sea tale starts with ‘This ain’t no $hit’!” – Edith Widder

If you read my preface sailing post about the events leading up to me spending two weeks on a sailboat with a guy I had never met, you’ll remember that I undertook this adventure wanting to feel alive.  Well, seeing my life flash before my eyes several times certainly accomplished that mission.  You’ll also remember that I stepped aboard knowing nothing about sailing but on a trip like this, I certainly learned a lot… fast!  When Brandon and I embarked on the week long sail from Marathon, Florida to Dry Tortugas National Park and back up to Key West, I had no idea what to expect.  Supposedly, we experienced more disasters in 7 days than he had in four months of owning the S/V Aloha.  Maybe it was bad luck?  Maybe sailing and I aren’t meant to be friends?  Either way, I thought I’d share with all you some of the stories of our sail, some pieces of wisdom I picked up along the way and some quotes from  people who know far more about sailing than myself.

The kayak landing dock at Dry Tortugas National Park

The kayak landing dock at Dry Tortugas National Park… pretty magical place

1) Sailing is More About The Journey Than The Destination

Dry Tortugas National Park: 100 square miles of open water and 7 islands, located in the Gulf of Mexico in the westernmost and most isolated of the Florida Keys, about 70 miles west of Key West.  The park is known for its snorkeling and scuba diving (a positive by-product of being a prime location for ship wrecks), birdwatching, kayaking and has a few primitive campsites.  It also contains Fort Jefferson, a massive masonry structure (the largest in the Western Hemisphere, made with more than 16 million bricks!) which was never finished as a fort but served as a jail during the civil war.  As one of the few United States national parks accessible only by boat or sea plane, it seemed like the perfect destination for our sail.

Spoiler alert: miraculously, we made it there and spent two days snorkeling the Windjammer shipwreck, swimming with barracudas the size of human legs, watching swarms of birds going crazy during mating season and walking around the nooks and crannies of the pink brick fort.

Made it to our final destination: Dry Tortugas National Park, Florida

Made it to our final destination: Dry Tortugas National Park, Florida

Was it worth a couple near-death experiences and three days of open ocean with barely any boats, islands or signs of civilization, at a painstakingly slow pace?  It depends on your perspective.  We could have arrived to Fort Jefferson safely and easily on a two hour ferry ride from Key West.  Would we have had the same appreciation for seeing a pink thing emerging on the horizon after days where we saw nothing but ocean, sun rises, sun sets and the occasional dolphin?  Would we have appreciated its rugged inaccessibility?  Would we have had any interesting stories to tell?  Absolutely not!

When I read one of Brandon’s books about a couple traveling the world on a sailboat, I quickly lost interest because they spent so much time talking about mapping their route, preparing the boat, orienting their sails for the weather and cooking dinner that they barely wrote about what happened when they arrived at their destination.   It took awhile but then I realized, when you’re on a sailboat, it doesn’t matter where you’re going, it doesn’t even matter if arrive because being at the mercy of the waves, sea and wind IS the whole point.  If you have a deadline and ambitious itinerary, don’t board a sailboat but if you want to grow in your appreciation of the places in between, there’s no better way to travel!

“Sailing – The fine art of getting wet and becoming ill while slowly going nowhere at great expense.” – from “Sailing” by Henry Beard and Roy Mckie

The act of moving has always been one of my favorite aspects of traveling, but on land, transporting yourself is trivial and the scenery is interesting.  On a sailboat, the act of transportation is the challenge.  Realizing this required quite a shift in perspective.

“There is nothing — absolutely nothing — half so much worth doing as simply messing about in boats. In or out of ’em, it doesn’t matter. Nothing seems really to matter, that’s the charm of it. Whether you get away, or whether you don’t; whether you arrive at your destination or whether you reach somewhere else, or whether you never get anywhere at all, you’re always busy, and you never do anything in particular; and when you’ve done it there’s always something else to do, and you can do it if you like, but you’d much better not.” – Spoken by Ratty to Mole in Wind in the Willows a children’s book by Kenneth Grahame (1859-1932).

The first glimpse of Fort Jefferson after days of empty ocean.

The first glimpse of Fort Jefferson after days of empty ocean.

2) Sailing Focuses Your Attention on Subtleties of The Sea

When I embarked on this trip, I wasn’t sure I’d like sailing.  There was something about boats that I never really enjoyed.  Brandon encouraged me to elaborate, “I guess I don’t like traveling by water because there’s so much nothingness in between.  When you’re driving, the road changes.  You see people.  You see buildings.  You complain about drivers who don’t know what their doing.  You can stop anytime, hop out and buy coffee.  But when you’re on a boat, all there’s only miles of sea that looks the same.  Don’t you get bored?  Don’t you drive yourself crazy?”  Sure, you certainly can’t stop the boat wherever and expect a cool beer in a frosted glance, a hot shower or a kitchen floor that doesn’t move beneath you. But not having that option forces you to absorb the surrounding atmosphere with a much higher sense of perception that helps you discover amazing things.

But when on land, it’s sometimes tempting to become so focused on the mission of arriving or accomplishing something that you completely miss the beautiful details of your surroundings and the subtleties of your environment.  Sailing slows you down and requires you to be perceptive about things like the wind and the waves and the position of the sun (because that can be linked to weather patterns).

“There is nothing more enticing, disenchanting, and enslaving than the life at sea” – Joseph Conrad

Despite the fact that I wrote about our miniature disasters at sea, because those are often the most entertaining (and easy) to tell, most of our time was spent bobbing along and allowing nature to reveal some spectacular sights.  When I took the time to look, the sea is never the same, even if there’s “nothing” there.  The color of the ocean was constantly changing, from a deep indigo with subtle sparkles as the sun streamed in, to a robin’s egg blue that allowed sight of the seaweed to peak through, to a slight bioluminescence one night that totally blue my mind.  We encountered a surprising amount of wildlife.  More times than not, we just heard a plunk and saw some kind of fin flapping out of the corner of our lives.  But several times, dolphins kept us company, fearlessly guiding the bow of the boat somewhere towards the horizon.  We saw birds hungrily peeking at a flock of flying fish, some awkwardly trying to stay stable in the air above.  One day, Brandon decided to try his luck at fishing, even though he hadn’t been able to catch anything since moving to the keys.  When he let his line out behind the boat, with some kind of generic fake bait, I was skeptical that it would amount to much.  His first catch was a pile of seaweed.  He got bored quickly after his first attempt but then tried again when he neared a rocky shoal.  He thought he caught another planty sea specimen and surprised himself when he reeled in a 19″ yellow tail.  A few shots of vodka and about 20 minutes later, we were dining like kings on super fresh, home caught fish!

Victory at sea: Brandon caught a yellowtail which we immediately consumed!

Brandon’s first catch in Florida, which he immediately morphed into a delicious meal.

While moments at sea usually involve the same combination of sun, wind (hopefully! Our lame breezes caused us to really appreciate a good gust that could get us somewhere!)  and waves, the combination of three provide a myriad of diverse experiences, if you’re paying close enough attention.  No day is ever quite the same and the slower pace of travel really creates the time and space to appreciate magical moments that you might miss surrounded by distracting and overpowering signs of civilization.

3) Sailing is An Exercise in Problem Solving

“When everything goes wrong, that’s where the adventure starts” – Yvon Chounard

When I first told my parents about this sailing trip, their first questions centered around the captain of the ship.  “Does he drink?  Does he smoke?  Those sailor-types often like to lie back and loose their minds to margaritas and marijuana, you know”.  While I reassured them that Brandon was a straight-edge, non-smoker, -drinker, drug-doer, I must confess that I similarly conceived sailors as chilled out people who spent their days working on their tan and maybe pretending to erect a fishing pole, every once in awhile.  I had e-mailed Brandon enough to know that he was always busy building showers, fixing something, helping hoist friends up the mast and learning new skills but I thought he was more the exception than the rule.  I thought once you had the money to buy a boat, the rest was a piece of cake.  Boy, was I wrong.

Brandon fixing something on the mast at Boot Key Harbor in Marathon, Florida

Brandon fixing something on the mast at Boot Key Harbor in Marathon, Florida

Boy, was I ever wrong.  Before setting sail, I spent almost a week with Brandon at the marina, helping prepare for our voyage.  I watched as he rewired the lighting system, revived his motor after a storm submerged his dingy, I heard about his friends trying to resow their sails, fix solar panels, keep the wood from rotting… the list of possible repairs never ended and required extensive knowledge about wiring, motors, construction, making things seaworthy, which typically involved more thinking than designing something for use on land.  Once you lift the anchor, there’s a whole other host of knowledge needed- you need to pay attention to how the waves are moving, how the wind is blowing, what other boats are doing then consider all this in relation to navigating where you want to go- how to avoid obstacles, which direction will get you moving fastest, what is the shortest distance.  These aren’t static situations either- it seemed like as soon as we optimized the sails for the the shortest, fastest route that won’t get us stuck, the winds would change.  Then there’s all the emergency preparation information like what do you do if your water runs out?  Your sail breaks?  You run out of fuel?  You get stuck somewhere?  You need a Plan A, B and C and you need to be alert enough to constantly monitor the situation and act accordingly.  You can’t be lazy or dumb to sail unless you’re rich enough to pay someone else to worry about these things for you, and that’s not a real sailor.

“The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails”. – William Arthur Ward

Despite #boatlife being far more difficult than I imagined, people keep sailing because for every bucket of pee you have to empty from the Head, every broken appliance you have to skip a snorkeling trip to fix, for every meal that you get sick cooking that you lose your appetite to eat, there are those precious moments when you have the right winds, you’re moving forward and everything just feels right with the universe.  Even though our trip wasn’t smooth sailing the whole time, the exhilaration of cranking up the radio and sing along to Lion King at the top of our lungs with no one around to hear, the glee of racing dolphins, the feeling of victory when we got ourselves to Dry Tortugas when the rest of the tourists lamely arrived on a ferry, that’s what keeps people addicted to this somewhat antiquated mode of transportation.  Sailing isn’t for the faint of heart but it offers a host of treasures for those passionate about it enough to deal with the ups and downs.

Songs of the Moment: Old Pine– Ben Howard & The River– Garth Brooks.

Movie of the Moment: Maidentrip (documentary of a 14 year old Dutch girl who solo sails around the world)

Book of the Moment: Love with a Chance of Drowning by Torre DeRoche

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  1. Brandon Capt; SV Aloha
    Jun 22, 2015

    I feel that while your experience was a disaster you have missed the point of the exercize. The story is a good one through the reality of it is, just that, it is a story. An exaggerated detail(though mostly true just from your perspective) of what occured. The weather is not so fickle as to give you want you want and sailing is best done in your own time not to schedules and the time lines of the the fast traveler.

    The fire was no more than an electrical spark due to the connection being wet. Dried and taped the problem was solved rather quickly. And most things we did was not blindly done in any sense. We worked to create a plan and committed to resolving the issue at hand. Communication and planning we pulled through some storms, blows and weather that most would not have dared to attempt from too much to too little wind it is exactly what you get, not what you want.

    I do not remember blindly swinging the gaff hook to pull up a crab trap but actively and very carefully being tied off to the boat and catching a crab pot to cut a line that was caught on the boat then diving the next morning to free the rest of the lines from the rudder.

    Your experience seem to have solidified your past biases towards sailing. This is and has put a stigma in sailing for your mind. As for the many who deem sailing to be worth it all, maybe we see the world in a different light and view the good with the great right along with the bad to be handled as a whole experience.

    While I do not agree with it all , you are correct in many things. It is your experience and your perception of what occured.

    Anything worth doing, is worth doing right. Anything worth loving, is worth everything.

    • Willow Cherry
      Mar 1, 2016

      What a great adventure experience and publication. One may see sailing as the closest to the earth and its raw elements we can get. There is no more humbling experience than being in a situation that requires life or death decisions. The pleasant reality that surfaces from the full experience of cruising (not just sailing) is one of the most rewarding endeavours realized by our human history. The word paradise comes to mind often, and is regularly exchanged between captain’s on radio traffic as proof of the reality. This is not to say that sailing is not an adventure, but as with most things there are good and bad days. The danger can be so real, yet the absolute euphoric, deeply satisfying paradise and piece of mind found is worth every passing storm, every drop of cherished water, every day I braved the storm in the tender to provision. Its the solitude of a Monks temple if you like, it’s a harbor of free concerts and friendly community events if that’s you cup of tea. Wheather you focus on the good days or bad days is personal preference, but if I think we all agree that the experiences are clarified, deeper, and more memorable than your general 9 to 5 jazz. I salute you both for your walks in life. To grow and experience things most don’t and have the tools those experiences equip us with is a blessing. Cheers

      • Katie
        Mar 1, 2016

        It’s so true @Willow and you articulated it so incredibly! I feel honoured that you read and commented on my blog. Thanks for your wise words!


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