St. Augustine: Sunset Sail with Live Music & Drinks

4.80

(294 reviews)

What’s the experience like?

We stepped barefoot onto the catamaran just as the sky started turning that weird peachy color over St. Augustine. The deck felt warm from the day, but there was this salty breeze that made me wish I’d brought a light sweater—typical Florida, you never know. Our guide, Mark, grinned and handed out plastic cups of margarita (he called it his “boat recipe,” which made me laugh). The band was already tuning up in the corner, and someone’s guitar string snapped with a sharp twang—nobody seemed to mind.

As we pulled away from the dock, people waved from shore. The Castillo de San Marcos looked almost soft in the fading light, not as stern as it does up close. I leaned against the rail with my drink and tried to catch every note as the music floated around us—some old bluesy stuff, some local songs I didn’t know. A couple next to us got up to dance and nearly spilled their wine; they just laughed it off. There were families too—kids chasing each other between grownups’ legs while parents tried to take photos without dropping their snacks.

The Bridge of Lions slid by on our left, its lights just flickering on. I could smell sunscreen and something sweet from someone’s champagne glass mixing with the ocean air. Mark pointed out where you might spot dolphins if you’re lucky (we weren’t, but honestly I didn’t care). At one point I closed my eyes for a second just to listen—the boat creaking, laughter behind me, that low hum of conversation you only get when people are actually relaxed together. It wasn’t perfect—someone dropped a bag of chips and there was a scramble—but it felt real.

I still think about how easy it was to just be there in that moment, no big agenda except floating through St. Augustine at sunset with strangers who didn’t feel like strangers for long.