As we begin planning for what we hope to be a fun maiden season with our sailboat, S/V Koko, we feel a mixture of excitement and, well, a bit of nervousness. Why nervousness, you ask? Because our planned trip is less about the destination and more about embracing the unpredictability of cruising—something not even the best-laid plans and no map can truly account for. Our past sailing outings have shown us that the best moments happen when we least expect them.

Our main quest for this year? To set sail from the sunny shores of the Gulf Coast in Florida, weave through the tropical beauty of the Keys, and leisurely make our way up the East Coast to Rock Hall, MD on the Chesapeake Bay. This trip is not just about delivering a yacht; we are delivering ourselves into the care of the rivers, and the bays, and the ocean, where time is but a suggestion and the journey itself is the star of the show.

We have penciled in our start date for March or April. Why? Because it sounds nice and gives us a cozy window to cruise up north, all while giving us a good buffer to beat the upcoming hurricane season starting June 1st.

So, where do we begin? How about looking at a map! The online map tells us that the direct distance between our starting point (Harborage Marina in St. Petersburg) and our destination (Haven Harbour Marina in Rock Hall, MD) is approximately 850 nautical miles (978 miles or 1,574 kilometers). Obviously, this straight-line distance does not account for the actual sailing route, which will be significantly longer because of the need to navigate around the Florida peninsula and up the Atlantic coast. If we were to take a commercial flight, it would only take about 2 hours, while a road trip by car would take around 15 hours (without the plenty of stops we normally take.) But what about sailing? Our initial, highly scientific guess estimates we should plan for about three months of relaxed cruising. This number comes from a complex algorithm involving crossed fingers, hopeful looks, and the occasional “What if we just stay here for a week?” Maybe we can come up with a slightly more informed estimate? We will dive a little deeper into this planning thing in some of the upcoming blog posts.

But no matter what, the only thing set in stone is our commitment to spontaneity. The wind decides, and we follow. Maybe we will discover a deserted island and declare it “The Isle of Koko.” Or perhaps, we will find ourselves anchored next to a floating ice cream stand (fingers crossed). So, here is to slow cruising, zero schedules, and a fun adventure. Because in the end, it is not about how fast we reach the destination; it is about all the unforgettable moments we collect along the way.