Thursday March 26, 2026
We made our easy 15-mile cruise into St. Augustine just after noon, greeted by one of those picture-perfect Florida days that makes you forget every rough mile that came before it.
Once we got settled, we did exactly what this town calls for—no plans, no schedule… just wandering. Since we’d visited four years ago and already checked off Castillo de San Marcos and the St. Augustine Lighthouse, today was all about soaking in the charm of the old town.
And wow… it was buzzing. People everywhere, energy in every direction. The streets were lined with the cutest little shops—fudge, ice cream, clothing boutiques—all tucked into buildings that date back to the 1500s. It’s wild to think you’re casually strolling through history in the oldest continuously occupied city in the U.S., founded in 1565 by the Spanish. Somehow, it all feels beautifully preserved without losing its liveliness. Just… adorable.
After a few hours of wandering, we found a cozy pub, grabbed an outside table, and treated ourselves to a well-earned drink. As if on cue, fellow Loopers from Happy Hour rolled up on their bikes and stopped to chat—those spontaneous meetups never get old.
That’s when the conversation shifted to weather. A front was rolling in, bringing some pretty strong winds right on cue for Saturday—our planned day to cross our wake. After a little back-and-forth, we looked at each other and thought… why wait? Decision made: tomorrow becomes a big push, and we finish a day early.
We wrapped up the evening with dinner at Saint—a newer Italian spot that absolutely delivered. So good, in fact, that we brought leftovers home… future us was very grateful.
On the walk back to the marina, we made one last stop at the always-fun Tini Martini Bar to cap off the night with a cocktail and a little buzz of excitement.
Because tomorrow?
We finish the Loop. 🚤✨
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