I am not a natural-born sailor. The sea doesn’t call to me and I don’t crave the salty air.
What I love is land; I love seeing long stretches of road from my window, mountains outside my doorstep and tall trees silhouetted against the sky.
But that isn’t to say that I don’t love the sea, the burnt orange sunsets, the surprise visits from dolphins or the primal satisfaction I get from covering long distances by harnessing the power of the wind like a modern-day explorer with an espresso machine.
It’s just that I’d rather explore land.
And it’s not because I get seasick (if iron guts were the mark of someone destined for a life at sea, then I fit the bill) or because I long to have the stability of earth under my feet. It’s because I love to run long and far, bike up and down hills, clamber up mountain sides, ski down them, play soccer and go roller-skating; all things that I need vast swaths of solid ground for.
I thrive in places where I can lace up my sneakers, step out my front door and run as far as my legs will take me; where I can sweat out the day’s frustrations and run away with just my thoughts whenever I want to without having to bother with lowering the dinghy into the water, fixing the cumbersome outboard on the stern, refilling the gas tank and waiting impatiently for the crew of Cheeky Monkey to get ready to go to shore, too.
Our friend’s dog, Sophie, demonstrating the dinghy-waiting game
So when my feet finally touched land in Antigua, after 20 days of sailing across the Atlantic Ocean, I kissed the ground and grabbed my sneakers. I felt sure in that moment that nothing would make me happier than spending a good long chunk of time — a year, perhaps — in the Caribbean, where a mere day sail would drop me in another stunning anchorage off an island covered with trees and hills and roads where I could run and explore to my heart’s content. I was keen to spend less time at sea and more time running back and forth across the lush, green Virgin Islands, which I’d only become briefly acquainted with a year earlier, when we sailed through on our old boat, Hideaway.
The Caribbean is well-known as an aquamarine Mecca for long-term cruisers and vacationing boaters. The USVIs and the BVIs, especially, are famed for their consistent winds and the fact that all you need for “charts” is a hand-drawn map showing roughly where the land masses are. There’s no need for a depth sounder, though sailing in the Virgin Isles requires you to keep a vigilant lookout, not for the shallows you might hit, but for the novice “credit card captains” who may confidently cut you off or, worse, smack into you on an otherwise beautiful day in the busy cut of Sir Francis Drake’s Passage.
Once, we made the mistake of sailing Cheeky Monkey through the famous passage while flying “The Big Banana,” our spinnaker. We watched nervously as a chartered catamaran headed straight for our starboard hull with no one on deck or at the helm. As the boat approached quickly, Ryan hailed him on channel 16 with increasing anxiety in his voice.
“Tropical Island, Tropical Island, Tropical Island, this is sailing vessel Cheeky Monkey.”
“Tropical Island, Tropical Island, TROPICAL ISLAND!”
Still no response.
“TROPICAL ISLAND, THE CATAMARAN ON A COLLISION COURSE WITH THE BOAT FLYING THE HARD-TO-MISS BIG YELLOW SPINNAKER, PLEASE PICK UP YOUR DAMNED RADIO!”
Plowing ahead on our fastest point of sail at a brisk 9 knots, we debated dropping the spinnaker and putting the engines on to steer away from a costly mishap, but in the time it took us to debate a course of action, we’d run out of time. So we blew our foghorn and Ryan and I began screaming in an attempt to wake up any sleeping or inebriated crew on the skipper-less boat.
A man and a woman with a baby on her hip eventually emerged on deck, at which point our screams grew louder with no effect on the charter boat’s course, which was now so close to us that I could have slapped the skipper upside the head from where I was standing on the bow.
Ryan was red in the face, bellowing about right-of-way and gesturing with his VHF radio as the man on the charter boat slowly walked to the helm without any show of alarm whatsoever. When he picked up the radio, the man simply said, “It is the rule that the boat on port tack must give way to the boat on starboard tack.” To which Ryan replied, “Yes, that is correct! And YOU are on a PORT tack! I am on a starboard tack! To clarify, as you seem to be confused, a port tack is when the wind is coming over the port side of the boat!” To which the man calmly replied, “That is not my understanding. I think you should consult your rule book again.” At which point Ryan wrapped the VHF radio cord around his neck and threw himself overboard. Well, not really. But that is what he looked like he might do.
But I digress. The risk of colliding with over-confident and under-skilled vacationing sailors in the Virgin Islands aside, there is a very good reason why so many boaters flock to the Caribbean in the winter to get a slice of the cruising life — the islands are stunning and not at all over-developed because most islands, with the exception of St. Thomas and other cruise ship ports like Sint Maarten, can’t be reached unless by boat. That, and the fact that you can sleep off the numerous coconut Painkillers you drank the night before, lazily raise your anchor sometime before noon, and reach yet another white-sand paradise in time to drop anchor and enjoy the sunset with a cocktail in hand, makes the Virgin Islands the go-to option for snowed-in sailors escaping the USA and Canada.
View of Maho Bay anchorage, St. John, from the top of a very steep hill
Plus, direct flights to St. Thomas and St. Maarten from New York meant if we stayed in the Caribbean for a year, friends could easily visit us from the States and, as an added bonus, we could spend more time with all our cruising friends who were semi-permanently based in the Caribbean, like Brittany and Scott (Windtraveler), Rebecca and Brian (Summertime Rolls), Genevieve and Eben (It’s a Necessity) and Peter and Jody (Where the Coconuts Grow). I say “semi-permanent” because cruisers are always on the move, but many of our boating friends have made the Caribbean their home for the foreseeable future.
But somehow, the next time I blinked, three months had flown by and we had spent most of our time anchored off some part of St. John or another. It seemed obscene to have spent so much time on just one island after we zipped so quickly from France to Spain to Ibiza, then across the Mediterranean twice (while also attempting to row a boat across the Med…twice), to a skimming stopover in Gibraltar, then on to Morocco, the Canary Islands and then across the Atlantic to Antigua, which meant we covered over 5,000 miles in the space of just five months. So how did we find ourselves spending 3 months on and around one Caribbean island?
The only way I can explain this is to describe what seems to happen to me after long bouts of moving fast and furiously. I suddenly get the urge to sit still for a while, develop a routine, wake up to a consistent view and get off the boat every day to exercise and explore. And, to me, St. John is the Goldilocks of the Caribbean islands — it’s not too remote (it has grocery stores, bars and restaurants) but it’s not too touristy either, since nearby St. Thomas is the sacrificial cruise ship port — plus, it is covered in well-maintained hiking trails that lead to the most beautiful and secluded beaches as well as untouched snorkeling spots.
Basically, after five months of constantly being on the move and always feeling like we were in a rush, it felt like a luxury to spend three months moving slowly from one anchorage on St. John to another, essentially oscillating between Maho Bay on the north side and Hansen Bay on the south side, depending on the direction of the swell.
You have to run uphill for quite a while to get this view of Hansen Bay
It’s the topography of St. John that drew me in and made me want to stay a while — the rolling hills, bleached white sand, palm trees and the stunning, idyllic bays that I could imagine being the backdrop for those widely shared zen-inspired quotes about life. But, more importantly, I’d heard about St. John’s 8 Tuff Miles, a race that runs every year from Cruz Bay to Coral Bay, along a road that soars up and down hills so brutal that cars struggle to make it to the top. It sounded exactly like what I needed after 20 days at sea with nowhere to run. And what better place to train for a run on St. John than the killer hills of St. John themselves?
So Ryan and I registered for the 8 Tuff Miles and began our training on the sharp hills winding up and down and around Hansen Bay, on the south side of St. John. We got into a routine of heart-attack-inducing hill sprints in the midday sun, starting “easy” with 4 miles of quad-burning uphill panting and, after a few weeks, worked our way up to 8 miles on the toughest inclines we could find, cursing every inch of the road and the masochist who thought this island was the perfect venue for a running race.
And then I met a die-hard local runner who told me about an inaugural 13.6-mile trail run on St. John just two days after the 8 Tuff Miles, which sounded strangely appealing after all the running I’d been deprived of on the Atlantic crossing. So I signed up for that, too. I offered to sign Ryan up, but the look he gave me after he finished the 8 Tuff Miles said he’d had enough near-heart-attacks for one week. Which left me and 33 other running fanatics to line up for an uphill half-marathon just two days after the brutal 8 Tuff Miles Race.
It turns out running every single trail on St. John from one end to the other is not only a great way to see the beauty and diverse geography of the entire island, but it’s the best way to gain an appreciation for just how many well-maintained trails the island has to offer. It’s a runner/hiker’s paradise, which makes it a paradise for Ryan as well, since he can just throw my running shoes at me when I’m getting irritable and send me off the boat to unleash some of my energy on 13.6 miles of trail options. Well, 13.6 if you have a good sense of direction. For the directionally challenged, like myself, it may or may not have taken 15.5 miles of running (off-trail, at times, as I followed creek beds I thought were trails) to get from one end of St. John to the other. Needless to say, I was in heaven.
1200 people turned up to run the 8 Tuff Miles on St. John
But this is where Ryan and I diverge in our traveling urges. I find a beautiful spot I can run around for a while and it makes me want to sit still and get to know the place. Ryan finds a beautiful spot (that he doesn’t mind running around for a while) and it makes him wonder what else is out there, either in the next harbor or across the next ocean.
Soon, after a few months of wearing down the trails of St. John and imbibing cocktails with friends at all our usual spots in the BVIs, I could see Ryan was getting the itch to move on again. So I took this as my cue to look up fitness options and hiking trails in the islands further south of us, as it seemed likely that we would work our way down to Grenada and spend a glorious hurricane season hanging out close to land. Perhaps I’d join the Hash House Harriers or the Crossfit gym in Grenada.
Except Ryan’s itchy feet seemed to be pulling him in a different direction altogether. He started mentioning with increased frequency the sailboats who were headed for the South Pacific as if he were summarizing newspaper headlines with a few not-so-subtle additions.
“Have you seen Starry Horizons is getting ready to go through the Panama Canal? Man, the Panama Canal…that’s going to be a blast, don’t you think?”
“Have you seen Vagabonde’s Facebook update today? They’re heading for the Galápagos. How incredible would it be to sail to the Galápagos?” (See what I mean about not-so-subtle?)
As time passed over me at a pleasantly slow pace in the Caribbean, for Ryan, the passing of time seemed to be driving him into an urgent frenzy. And the more Ryan excitedly mentioned what other boats were doing and where they were going, the more it became clear that Ryan’s itch would only be cured by following in their footsteps.
“We can sail the Caribbean any time in our lives,” Ryan argued. “But I don’t know if we’ll always be able to cross the Pacific. I think we should go for it.”
“But we just crossed an ocean,” I whined. “I like it here. I like running. I like getting off the boat.”
What’s not to like about this? (Maho Bay)
“You can do that in the South Pacific!” Ryan said. “I promise. You can go surfing. And wind-surfing. And kite-boarding. By all accounts, the islands in the South Pacific are just to-die-for.”
And so he persisted, despite my protests against being marooned on a boat for weeks on end with nowhere to run. As a tactic, I reminded Ryan of the torture that is being stuck on a boat with me going out of my mind from inactivity. Had he forgotten all those times I threatened to get my own boat or, at the very least, a hotel room on land? In a place far, far away from the boat? No, he hadn’t forgotten. But he would not be deterred. It only increased Ryan’s motivation to research the quickest route from the Galápagos to the South Pacific and then talk to me about it as if there were no concern whatsoever that I might kill him and throw him overboard two weeks out to sea.
But, given time to mourn my loss of endless running options, I started to come around to the idea of sailing across the Pacific. Involuntarily, I started to get excited about the idea of sailing up to sea lions and sea turtles and blue-footed boobies in the Galápagos and I started to dream of the postcard-perfect waters of the South Pacific and wonder what we might find there.
Because that’s how this boat life works for me. To me, a boat is an adventure-ship that allows me to pull my mobile home up to the most extraordinary places in the world, places I might never get to if I only traveled by plane or car, places that offer opportunities for exploration and learning that make the long, inescapable journeys at sea completely worth it. And, of course, there are the extraordinary experiences of the journeys across oceans themselves, which I wouldn’t trade for any stretch of land. Those experiences at sea, when we are forced to be completely self-sufficient, have become the Jenga blocks, stacked one on top of the other, that have formed my character and informed my self-confidence. Because there’s nothing like solving a problem, big or small, in the middle of the ocean or in the heart of a raging storm to test your inner strength and mental fortitude.
This is also how the push and pull of my and Ryan’s independent enthusiasms work to create the tumult that is our co-planning for the future. Ryan has a tendency to dream up insane plans, latch onto them, and introduce them like there really is no better option. To illustrate, here are a few quotes from past conversations:
“There’s a gala for the Tennis Open going on over there. Hey, look, there’s Jennifer Capriatti and Monica Seles! C’mon, let’s crash it.”
“I think I might take a job in Sudan for a few months so I can pay off my debts.”
“My school just shut down their teacher training center. I was thinking, what if we started a teacher training center?”
“I was thinking, we should buy a sailboat. Yes, I know we don’t know how to sail. But from what I’ve read, that’s not important. We can learn.”
“I’m tired of New York. We have a boat. I say we just sail out of here and see what happens. We can hire someone to run our businesses. How hard can it be?”
“I’ve just signed up to do the Clipper Round the World Yacht Race.”
“I have an idea. Let’s buy an old, beat-up car in England and drive it to South Africa. Oh, it takes eleven months? Scrap that. Let’s hire a car in Johannesburg and drive it to Cape Town.”
“I have an idea. Let’s rent a camper van and drive across Australia.”
“Eben and I have signed up for this race in Tanzania where we take a beat-up fishing boat with makeshift outriggers, a plywood rudder, a bamboo mast and a handkerchief for a sail and we sail it to Zanzibar.”
“Let’s sell the businesses and buy a bigger boat.”
“Let’s scrap the Caribbean and go straight for the South Pacific.”
Each of these conversation starters were met with my immediate skepticism (because someone has to think these things through, right?). But once the seed of Ryan’s idea was planted, it often started to take root and I found myself imagining the next place we might end up. And I felt a gurgle of excitement in my gut when I thought about what this next potential phase of adventure might offer in the way of new land to explore.
Sometimes I even found myself adding my own mad-cap schemes to the mix. Take, for example, these choice quotes:
“There’s a marathon coming up in two months. I’ve never run one, but I think we should do it.”
“I’m applying for a summer internship in Azerbaijan, Armenia and Georgia. It’s just for a month or two.”
“Let’s go to New York. I’ll get my Master’s degree and we’ll be out of there in two years, tops.”
“Property in New York City is outrageously expensive! Let’s buy a log cabin in a ski town instead.”
“I found this adult ski racing program I want to join.”
“Have you seen that movie Whip It? Well, there’s this roller derby team recruiting players…”
“I want to start a blog. Can you build me a website?”
“There’s an all-female rowing crew looking for someone to row across the Atlantic with them. It would take about 45 days. At least. No? Not a good idea?”
“There’s an all-female rowing crew looking for someone to row around the Isle of Wight with them. I volunteered.”
“There’s this rowing race across the Mediterranean…300 miles…”
Upon further reflection, perhaps it’s not just Ryan who pulls our plans in all kinds of crazy directions.
But I stand by my statement: I’m not a natural-born sailor.
I am a lifelong traveler and adventurer; someone who craves change — new experiences, new smells, new foods and new thrills — always. So sailing fits nicely alongside my own desires for travel and adventure. And once my momentary skepticism has passed and Ryan’s enthusiasm has won, I am always thrilled by the prospect of discovering yet another strange, new place in the world.
This process of navigating towards the future with Ryan has a kind of ebb and flow, like the sea — sometimes I find myself fighting the current to get where I want to go. But, sometimes, it occurs to me that maybe it’s better to just relax, go with the flow and see where the next wave takes me.
And it looks like this next wave is carrying me off to the South Pacific.