Sailing Through Seasons: Reflections After Living on a Sailboat Through the Winter

Post by - Published on 04/11/23 13:35 PM

With a fresh college degree on my desk, a new remote job, and an ever-evolving love for the sea, I quickly found myself spending my first-year post-grad living aboard…in the winter…in Maine.

Let me rewind:

My life revolves around the ocean. I grew up exploring the nooks and crannies of the Coast of Maine and appreciating the sea from a young age. Growing up on the water taught me the value of seeking new horizons, and I developed core passion and enthusiasm that has carried me through my life.


As a young adult, I remained close to the sea by working as a launch operator at my local yacht club. Here, I was introduced to life-long mentors, inspiring travelers, and dear friends. I became intertwined with the cruising community, and within no time I had sparked an unwavering dream of long-term sailing and living aboard. My enthusiasm for sailing spread like wildfire at the club, and before I knew it, a friend of a friend offered me the first steppingstone towards a life on the ocean, a humble little O’Day 25 called Cita, at no cost. I lived aboard Cita for 4 summers.boating-wave-min

When I graduated college, I found myself with an amazing remote job in the industry I
live and love (😉) which enabled me to sail, cruise the coast, and continue my semi-vagabond lifestyle. Whether I found myself in busy Portland Harbor, or the islands of Penobscot Bay, I worked from Cita all summer long, building the bank, and having fun while doing it.

All Aboard!

When fall rolled around, the decision to spend the winter aboard was an easy one. My father offered me his larger, more capable sailboat, a Beneteau 39.3 called Mamá Cita, for the winter months, which I gladly accepted. The two boats rafted up, I transferred all my belongings from cute little Cita, over to Mamá Cita, and settled into what would be my home for the next 6 months.

On October 12th, the mooring field at the yacht club was thinning out. With only a handful of boats still in the water, we left our mooring, and motored across the harbor to DiMillo’s Marina, located in the heart of Portland’s Old Port. My partner, Jack, decided to take the ‘winter-aboard-leap-of-faith’ with me. I’ll admit… I contemplated whether this was a good idea for our relationship (after all, he’s from Connecticut, and had never endured a Maine winter before) but figured: “Hey! If we can make it through this season aboard a sailboat, he must be a keeper!” So, the two of us nestled into our slip, connected to shore power, and began preparing the boat for a long, cold, snowy winter in Maine.

This uncharted territory was daunting. It was also exciting. I was enthused with the idea
and stoked to be doing something out of the ordinary while remaining close to the sea. We sailed through November, enjoying the islands of Casco Bay without the crowds, but winterization was on our minds. We knew that preparing the boat would be a learning curve, and we soaked up knowledge from other winter liveaboards to position ourselves in a way that would be most comfortable as cold weather approached.


"How Do You Stay Warm?"

By the middle of December, our sails and canvas were stored, our engine was winterized, the dock lines were doubled up, and the boat was shrink wrapped with clear plastic. Although sailing season was over, winter had just begun.

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We got a lot of questions this season, mostly along the lines of “How do you stay
warm?!”. We heated the boat with 2 space heaters, which seemed to do the trick. The clear shrink wrap also helped with temperature, as it created a greenhouse effect, collecting heat from the sun. Other than two brutal cold snaps, which I’m sure New Englanders remember, the cabin’s temperature remained over 68 degrees, all winter long. Despite countless friends and family offering us their guest rooms and couches to flee to, we were just fine through the thick of it. The boat truly feels like home.


Of course, we did face challenges. Humidity being the biggest antagonist. With a warm
boat, a cold ocean, and a serious lack of insulation- this was inevitable. We troubleshooted this with insulation boards in our cabin, a (slightly obsessive) fan-rotation routine, and a massive dehumidifier– which ran 24/7 for the past 5 months. Humidity caused some havoc, but no harm.

Aside from humidity, we did get up close and personal with a few gnarly Nor'easters over the winter. It was bound to happen, and we were prepared. The power of the ocean never fails to amaze me. Although we were uncomfortable, and sometimes quite humbled, the Mamá took care of us, and remained a brick house through it all.

Reflecting On My Experience

All this being said, living aboard this winter was surprisingly easy, and I would do it all
again in a heartbeat. As we prepare to leave our slip at DiMillo’s, and head back out to our
mooring for the summer, I reflect upon my experience:

  1. Living aboard through the winter was undoubtedly an adventure. A fun one. It was a unique way-of-life that challenged me in new ways and pushed me out of my comfort zone. From big events like Thanksgiving with 8 dear friends around our salon table, to trekking down the docks after a February blizzard with skis on our shoulders, I found wonder, great fun, and adventure throughout the entirety of the winter.

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  2. The ocean boasts infinite power, but also holds deep deep love. My relationship with the sea has remained constant through my life, which is why it was no surprise to friends and family that I chose to live aboard this winter. These new rugged and cold horizons provided me with a fresh view of my love for sailing and the sea and sparked a new level of wanderlust within me to keep reaching towards the unknown.
  3. Happiness is only as good as the people you share it with. Although I often dream of far-off places, and I am sure I will explore plenty of new horizons in the coming years, I found adventure right at home, with the people I love. I was lucky to share this liveaboard experience with my partner Jack, who proved himself to be a hardy Mainer, along with my parents, grandparents, family members and friends who live nearby. I wouldn’t trade this winter in Maine for the world.

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Well, it’s now April. We made it through an entire winter in Maine aboard Mamá Cita.
Not too many things broke, our water pipes only froze twice, and my relationship is still thriving.

I’ll call that a win! In all seriousness- this experience couldn’t have gone better.
Will I end up in Portland again next winter?! Who knows! I know of the perfect app to
help me find great marinas down south… the next adventure is calling!

If you have any questions about living aboard in the winter, email me at

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