I’ve never been a sailor. A boat man. In a city surrounded by water, with a nautical history going back over 450 years, I’ve always liked staring at the agua, but not necessarily floating atop it.
That all changed this past Saturday thanks to four simple words: “Oars at the ready!”
With that we launched the chalupa, a truly special boat. Two weeks ago it was christened the San Augustin, but thanks to low tide, it sat stuck in the mud.
Saturday, the boat I’ve dubbed the S.S. Chalupa, finally stretched its legs (or whatever boats stretch) and made its maiden voyage under oar power, led by our captain and coxswain, Sam Turner.
How lucky I was to man one of those oars on this 37-foot replica of a 16th century Spanish longboat — a local workhorse in colonial times that helped move men and cargo off ships, as well as explore up and down the coastline. It was the pickup truck of the 1500s.
Dedicated members of the St. Augustine Maritime Heritage Foundation, with the help of the Lighthouse Archeological Maritime Program and the Fountain of Youth Archaeological Park, hand built the chalupa using old world techniques. It’s to commemorate St. Augustine’s 450th anniversary and a fitting tribute. The wood glistens like chrome. It’s a floating Cadillac.
But there’s always trepidation at the beginning of anything. Like when you step onto the boat for the first time and think to yourself, “I wonder if they remembered all the nails.”
Then the coxswain yelled “Stroke!” and those outstretched oars bit on the water, propelling us forward. A chill ran through me.
We weren’t only preserving history — we were living it.
Coasting up and down the bayfront as tourists and locals waved and took pictures, it was easy to get lost in the moment, imagining myself rowing ashore supplies (rum!) as the Castillo de San Marcos loomed above and those Atlantic breezes tried to hold us back. What must it have been like in those early days? What a taste I got.
And the beauty of St. Augustine. Dolphins splashing by and a slow cruising manatee hugging the shoreline. We watched cannon fire from the Castillo and rowed below the Bridge of Lions before docking beside El Galeon, dwarfed by that ship’s sheer size.
It made me realize what a truly special place we live in. That there is nowhere else like this — and that I am now part of a new tradition.
A legacy. With each stroke, we literally put into motion what so many have labored for years building. It was an honor to be aboard it, and humbling to play a role, as small as it was. The boat builders are the real stars. They’ve brought history alive. We just paddle it.
A truly special boat in a truly special place. Sun-baked, exhausted and arms aching, I didn’t want to get out of the chalupa after we rowed back to the Fountain of Youth. Didn’t want the experience to end. And now, I can’t wait for another chance to hear those four simple words — “Oars at the ready!” — that mean I’m a sailor now.