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  • Molly Gone Wild

How We Ended Up on a Sailboat

Updated: Jun 13, 2022

Woman on a sailboat

Had you asked me a few months ago what I thought I’d be doing in December 2021, I most certainly would not have guessed “living on a sailboat.” Yet, here I am, typing away, on a 35-foot Beneteau sailboat, a few days into one of the biggest leaps of faith I’ve ever taken.

Here’s the backstory. Four months ago, in my wedding vows to Tyler, I told him it was my intention as his partner to make space for his dreams, to encourage his passions, and to maintain a commitment to travel and exploration. For him, those passions and dreams happen to include sailing and living on a sailboat. Tyler has spent a lot of time on the water in kayaks, rafts, canoes, rowboats, and sailboats but never had the opportunity to fully immerse himself in sailing life.

Three months ago, we had a lot of long discussions about when we might be able to make this dream of his come true. What if we just went on a sailing vacation for a week? What if we waited until retirement? None of the options felt quite right. In the end, despite the many reasons not to, we decided now was the time.

Two and a half months ago, Tyler flew to Florida to look at pre-owned sailboats. He drove from one side of Florida to the other but didn’t feel like he’d found “the one.” On the day he was supposed to fly home, the broker called and said he had one more boat he thought Tyler might want to take a look at. Tyler drove back to St. Petersburg where he boarded the beautiful Cristina. She was a 35-foot Beneteau sailboat whose previous owner took meticulous and loving care of her. She needed no major repairs, boasted a large, comfortable owner's cabin, and came outfitted with all of the electronics we would need. Tyler called me and said, “I think I found us a boat.”

Two months ago, we officially became the new owners of Cristina. Suddenly, this faraway “what if maybe someday” dream was a solid and certain reality. We knew we would set sail from St. Petersburg but that was about all we knew. We started researching destinations and routes, watching YouTube videos, reading blogs, and more as we tried to cram as much information into our heads as possible.

Sailboat at anchor

One month ago, I still knew pretty close to nothing about sailing. The idea of living on a boat sounded completely intimidating. I was lucky enough to find an amazing, all-women, American Sailing Association 101 sailing course hosted by Modern Sailing School & Club in Sausalito, CA. After four days on the water, I felt like I had been handed the keys to a whole new world. Instead of staring at the mess of lines onboard in terror, I could call to mind the names and purposes of each. The course boosted my confidence a thousand-fold and I felt ready (enough) to take on this next adventure.

Two and a half weeks ago, we packed up our car and drove across the country to St. Petersburg, Florida.

One week ago, we climbed aboard our new home for the first time. We spent a week docked at the St. Pete Pier, working on our boat. We fixed what was broken (mostly Tyler), cleaned and scrubbed (mostly me), shopped for supplies (both), and packed Cristina to the brim in preparation for a few months of sailing.

And then, just like that, we set sail! We spent our first night docked at a friend’s house just south of the city before heading south from there. The first few days have been surreal and scary and amazing all at once. In the quiet moments when the wind is singing through the sails and the sun in dancing off each wave and ripple, I have started to feel the peace and expansiveness that so many sailors must know. It’s alluring, and a bit unnerving still, and I can’t wait to go deeper into the world of life on the water.

I also have to give a big old shoutout to Tyler for bringing so much adventure into my life and for helping me push my boundaries. Life with him is never, ever boring and, for that, I am so grateful!

Man on a sailboat

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