An important part of cruising with confidence is doing it on your own terms. In today’s post, Kimberly Ward, a member of The Boat Galley team, shares how she and husband Michael crafted their best cruising life.
I was not born a sailor. Nor did I grow up sailing. I also did not come to love sailing organically, revealing a hidden passion. In fact, even now, I will often insist I am a gardener, not a sailor. I fell in love with a sailor.
Michael and I were both technical consultants when we met in Pittsburgh in 2001. He lived in the Boston area, and I in Northern VA. He was building a house on Buzzards Bay as I was fleeing the workworkwork money-consumed world of DC for Nashville, TN.
In 2003, I married my sailor—the proverbial son of a sailor—and his sailboat, Wayward, a 1973 Tartan 34.
Three months after the wedding, we took off on Wayward for a six-week cruise from MA to Halifax, Nova Scotia. I was completely clueless. Even that is an understatement. I had no idea how to be a cruiser. I did not even know what we were doing was even called cruising! Michael was Captain, First Mate, and Crew. And though I was reasonably proficient at following instructions, I was not even a good cook at that point, much less proficient at provisioning and cooking on a boat. I was basically just along for the ride.

Having married into it, sailing was kind of like in-laws. Over the next decade, as we sailed on weekends and usually managed a two -week vacation on Wayward each summer, I got to know my new in-laws and became a solid First Mate. I learned about safety on board, particularly man overboard situations. I learned how to manage the boat in an emergency. And I learned how to cook!
Both Michael and I love to travel, and along with a myriad of other trips, we talked about some sort of a big trip on the boat as a family. However, actually defining what that meant and planning for it were relegated to ‘some day.’ In 2012, friends from consulting days—both new to sailing just a couple years before—sailed into our cove. With their two young children and new skills, they took creative approaches to get out cruising. They hired a captain, crew, and/or flew part of the family to meet the boat, until they were comfortable cruising as a family.
I realized that cruising was not a one-size-fits-all sport. It does not require us to sell everything we own, move onto a boat full-time, and sail around the world. Any other ‘all-or-nothing’ thinkers out there? The trick for us was to come up with a trip to fit our family’s needs. Not those of anyone else out cruising, not even those of our friends anchored in our cove. Put away the measuring stick. Comparison could kill our dreams before they had started.
My Captain and I created a cruising world that worked just for us. Michael and I talked through possible one- and two-year itineraries, a time period we were both comfortable considering. We took an initial stab at a budget and refined it multiple times. Our dream started to take shape.
And I realized I did not have to know everything to start. It was a novel concept that I just needed to see the next step, not the entire staircase. Slowly, over time, as I learned more and more, I began to gain confidence. I participated wholly in the boat buying process (we sold our monohull, Wayward, and bought a Gemini 105Mc catamaran), as well as the refit, gaining valuable skills along the way.
In 2014, we rented our house and set out on Ally Cat for two years, sailing from MA to Grenada and back. I learned more in those two years—both about myself and cruising—than I had in the previous forty-six!

And I am still growing as a cruiser. Amusingly, I still don’t consider myself a sailor.
Last winter, after moving Ally Cat from MA to FL in the fall, we spent about six weeks in the Bahamas. Not fully retired yet, our schedule allows us to work nine months, and snowbird January through March. Seasonal cruising is yet another way for us to cruise. My sailor gets his sailing fix and I am back in the spring in time to plant my veggies.

Kimberly is a writer, an oyster farmer, a gardener, and, yes, a sailor. She is also part of The Boat Galley team. Her first book, Crew of Three: How Bold Dreams and Detailed Plans Launched Our Family’s Sailing Adventure, is available on Amazon and everywhere books are sold. Learn more on her website.
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