Ocean to Ocean
From the place to the person
Bet you didn’t think another one of these would pop up in your inbox did you? This dispatch of Anchoring is Free comes to you from the dry, stable, unmoving land of St. Thomas. After 10 days and 1300ish miles at sea I wasn’t quite ready for how much I’d appreciate finally coming into harbor and dropping anchor. However, even as I say that I am already getting excited for my next passage. But all of that we’ll get to later, for now I just want to say that I’ve been inspired by my girlfriend Phoebe’s unwavering commitment to her blog, The Dish, so I figured I’d give this another crack. This blog started as a chronicle of a great sailing adventure Jan and I embarked on a few years ago and will remain a place for me to capture sailing endeavors, so don’t expect any updates in the near future.
This latest adventure has been my first foray into the illustrious tradition of ocean passages. My offshore experience sailing is very limited so when I was given the opportunity to join for a passage south from Bermuda to what was initially Antigua, but eventually turned into the US Virgin Islands, I quickly jumped on it. The chance for such an experience came about somewhat randomly, as I was put in touch with my high school roommate Becker’s girlfriend (Alecia)’s dad Leo a few months ago, confusing, I know. During this initial call, he pitched me on joining him sailing from Maine down to Florida and beyond. I was unfortunately not able to commit to the longer journey and honestly forgot about it until a few weeks ago, when I got another call from Leo asking if I’d be interested in helping out with this passage. After a few phone calls to the parents and a quick check of the calendar, I bought a plane ticket to Bermuda. Having never met Leo I really had no idea what to expect, our interactions so far had consisted of two phone calls about 5 minutes long each. After arriving in Bermuda I got a cab to the town of St. George’s where Leo was waiting for me to check me into customs and help bring my stuff out to the boat. It was quickly apparent that Leo would be a great travel companion for an adventure of this magnitude. For one, he had the best attribute an adventure buddy can have, making it happen. Namely by providing the means of transportation for said adventure, which in this case is a ruggedly beautiful Garcia Calva 34 named Ida.
After squaring away my stuff onboard we set about enjoying Bermuda while we waited for our weather window a couple of days later. Having been in Bermuda for a few weeks already, Leo had a good lay of the land. Some of the highlights were the Swizzle Inn at which it is imperative to buy a t-shirt for the name alone, but also because it is an iconic bar of Bermuda, and therefore recognized by sailors around the world. One of Leo’s friends Suzy, who got the idea for long form sailing adventures into his head, has a t-shirt from the Swizzle Inn dating back to the 1970s. One of the incredible things about Bermuda is it’s place among sailors around the world as a bucket list destination, and the rich sailing history is apparent everywhere you look. The anchorage around us was filled with boats of similarly minded sailors, some getting their first taste of ocean passages such as me, or seasoned veterans who stop by every winter on their way further south. One of these sailors tuned out to be a lovely fellow by the name of Jerry, whom with we ended up sharing several drinks and meals together. Jerry hails from Spicers Marina which is only a stones throw from Fishers Island (small world!), and is a born and bred adventurer. Having done most of his exploring on land, including the full AT, he only recently started sailing about 5 years ago after retiring, but has sailed solo from Connecticut to the Caribbean 4 times already. After getting a taste of how unforgiving but beautiful ocean sailing is, I have the utmost respect for those who manage to make these passages alone. So for that I tip my cap to you Jerry and look forward to seeing you up in our neck of the woods at some point.
After a couple short days in Bermuda we made our final preparations to head south and cleared customs Wednesday afternoon to get an early start Thursday. At 5:30am we pulled anchor an began motoring out of the harbor under the stars. The excitement was palpable. Leo had recently done the passage from Cape Hatteras to Bermuda so had some idea of what to expect but I was flying blind. As the sun rose we were greeted to amazingly calm seas which may have lulled us into a sense of security as we watched Bermuda slowly slip over the horizon. It’s hard to describe the feeling of seeing nothing but ocean any way you look. It fills you with equal parts awe and dread as you know you are alone and at the mercy of whatever comes your way. Someone once described the ocean to me as a desert and once you’re out there it most certainly feels it, as your only real reminders of life are the occasional flying fish and tropic bird.
The first few days passed without incident as Leo and I got to know each other during the day and settled into our split night watch routine. In this system Leo would go to bed as soon as the sun set, and then I would sail solo until around 1am when he would get up and take over until the morning. As Jan can attest from our sailing, the days are filled with long periods of silence punctuated by discussion of any topic under the sun. In this aspect having someone you have never met brings many advantages, especially on a journey like this where there is nothing but the occasional squall, or cargo ship passing by to interrupt the days blending together. And blend together they did, I struggle now to differentiate them already but can tell you some of the highlights overall. On the third day of the passage Leo and I had our first success fishing. In the span of about an hour we were able to bring in two beautiful Mahi Mahi.
The fish were quickly dispatched and turned into an amazing lunch with the extra meat thrown into the freezer for a later date. Quickly after ticking that box, Leo began to lust after catching a Wahoo, an obsession that was rewarded a few days later. I woke up to Leo screaming from the cockpit about something and dragged myself out of the bunk to see him pulling a beautiful wahoo right up onto the deck. This fish too was quickly turned into the latest iteration of lunch a few hours later.
Lunch is a funny thing on ocean passages, as it feels like the only meal that you can have some real routine around. Many days I found our most involved meals would be made around lunchtime, usually being some form of the fish we just caught. As night approached, we found ourselves preoccupied with other tasks to ready the boat for the night ahead, making it hard to devote time to making a good meal. The best example of this was the legendary beef stew. The night before we left, Leo made us about a gallon of beef stew in a pressure cooker that became our dinner for the next 5 days. While convenient and filling, the luster wore off a little quickly and we found ourselves dreading the meal near the end of the pot. This kind of energy saving I found was a good barometer for the rhythms set on passage. Once offshore many of the routines you become used to no longer apply. This became all the more apparent as sleep and fresh food become more scant as the journey rolled on. Making it all the more difficult to take the time and energy to shower or make larger meals. It should be said that on the lighter calmer days we were able to do such things easily but when the sea state began to pick up, it became harder to perform the tasks at hand. While that is the case, I think we ate relatively well during our time at sea, mostly due to the presence of the fish we were able to bring in.
Rhythms are important in life while at sea and on land, and one of the constants that kept the days interesting was watching the sky and ocean interact, especially as sunset approached. Each sunset at sea has so many different phases and characteristics. Watching them form over hours gives an appreciation to their complexity that I rarely get to acknowledge in New York City. I remarked to Leo at one point that if you pitched ocean passages to someone who has never sailed they sound incredibly boring. It involves flurries of intense work when the conditions change, and then hours upon hours of just staring at the sky and waves. While on paper this doesn’t sound super enticing, the prospect of just hanging out on the ocean appeals to both Leo and I tremendously, so we thoroughly enjoyed our days looking around at the horizon.





Speaking of rhythms, sleeping was a different story. I luckily have the ability to sleep through nearly anything, as my parents and brother can attest to, but Leo had a much harder time accumulating sleep during the passage. By the end of the 10 day passage we reckoned that he had only been able to get around 10-12 hours of sleep the entire time. How he was functioning by the end is hard to say, but Leo is not one to quit and out there you don’t have much of a choice either way. There was a lot I learned from Leo this trip and that kind of perseverance was just one lesson. Another trait you can immediately see upon meeting him is his fundamental belief in himself and his ability to figure out how to do literally anything. This journey is a case in point. He went from no sailing experience to at the age of 30 hopping on a boat for the first time and deciding then and there he would some day sail to far off places. And what a journey it has been for him so far. From solo sailing all over Maine into Canada and beyond, to recruiting friends to join him for his first ocean passages, his story has been an awesome one to just be a piece of.
After the initial calm seas we enjoyed fishing the first 5 days, the seas finally built up to true ocean strength. Most of our journey south we were running from a massive storm heading across the Atlantic, which finally caught up to us a week into the trip. And when I say massive I mean massive, this storm while touching us a couple hundred miles north of the Caribbean, was also hitting Iceland at the same time. Fortunately we only caught the edge of it but it was a sobering reminder of where we were in the pecking order of nature. The ocean seems to have a way of picking up the second you get a little too comfortable.
As we neared our (altered) destination and the lights became apparent along the horizon, there suddenly came this rush of energy for the two of us. We could finally start to really dream about that hot shower and stable seas after all. As I finished up my watch and went to bed, I had a hard time getting to sleep as the excitement was hard to subdue. Leo managed to bring us into harbor around 3:30am and set an anchor for us. While I was not awake for the moment the boat finally came to a rest, Leo said it was one of immense relief. After popping down and getting a much deserved few hours of sleep, Leo and I woke up in the Magen’s bay on the north side of St. Thomas. Right as we went to make coffee and take in the view, we were greeted by Leo’s friend Ocean and his son Adrien paddling out to greet us. Ocean’s story is one that deserves a book and thankfully his mother Suzy (whom I mentioned earlier of Swizzle Inn t-shirt fame) is in the process of writing one! Suzy and her husband Ron raised their two sons Ocean and Forest while sailing around the world on their boat Catania. Being around them the last two days, it’s hard to not be amazed by the anecdotes and stories that have made their lives so fulfilling. While I look forward to the book, back to the story at hand. Being greeted by friendly faces that quickly took us to shore to make us breakfast and coffee made the end of the chapter as seamless as possible. While we had initially set of for Antigua, neither Leo nor I are currently missing it due to the amazing hospitality of of Ocean and Suzy.
While I sit here writing this on the porch of Ocean’s house I both anticipate and dread my flight home tomorrow. I miss my family and girlfriend Phoebe dearly, but this passage has stirred something in me to go on and find more sailing adventures. Part of me wishes to continue on from here with Leo exploring the island chains. But those opportunities will come, and there are already rumors of Ida making her way into the arctic in the next few years. So until the next adventure I’ll leave you with a quote from Suzy about ocean passages and as is tradition a photo of my writing station. “Ocean passages are like giving birth. In the moment they’re the worst thing in the world, but as soon as you’re done you’re thinking about the next one.”








So happy for you 🩵 and how cool to make some inter generational friendships - so important imo!
Great read Teo! Sounds like quite the adventure.