St. Augustine: Wine Tasting Cruise & Historic Bayfront Views

Summary

Wine tasting on the water as st augustine glows in the evening

You’ll board right on St. Augustine’s waterfront for an early evening cruise with six wine tastings as you pass landmarks like Castillo de San Marcos and Mission Nombre de Dios. Friendly guides share stories and keep things light while dolphins sometimes tag along beside you. It’s relaxed, social, and gives you a whole new angle on Florida’s oldest city.

What’s the experience like?

There’s this moment when the boat engine quiets down and you just hear gulls and the soft clink of glasses — that’s how our wine tasting cruise in St. Augustine started. I’d never seen the Castillo de San Marcos from the water before; it looked almost gentle in that pinkish light, not at all like a fortress. Our guide, Jamie, tossed out stories about pirates and Spanish explorers like she was talking about old neighbors. She handed me a glass of something floral (I forgot the name, but it was local) and I could actually smell orange blossoms drifting over from somewhere onshore.

I kept thinking I’d be distracted by all the city noise, but honestly, it felt like we were floating in our own little bubble. The Great Cross at Mission Nombre de Dios came into view — huge and shining — and someone next to me whispered they’d never noticed it from this angle before. We tasted six wines in total, each one with a quick story or joke from Jamie (she teased my friend for asking if rosé counts as “real” wine). Dolphins showed up too, which I guess isn’t guaranteed but felt kind of perfect.

Flagler College’s towers peeked over the skyline while we drifted under the bridge; there was this faint salt tang in the air and a bit of breeze that made me wish I’d brought a jacket. The crew kept things relaxed but made sure everyone knew where to find life jackets (and also where to get more wine). No one rushed us — we just sipped, watched pelicans dive, and let the city lights come on one by one. I still think about that view sometimes when I’m stuck in traffic back home.

Step-by-step itinerary

Day 1 — Evening wine tasting cruise tour

• Meet for boarding and safety briefing
• Cruise past Castillo de San Marcos
• View the Great Cross from water
• Sample wines near the bridge
• See Flagler College from the water

Top questions

How many wines do you taste on the St. Augustine cruise?

You’ll sample six different wines during the cruise, including some local favorites.

Is there a guide or commentary during the wine tasting cruise?

Yes, an experienced local guide provides live commentary about history, wildlife, and landmarks.

Does this tour include pickup from my hotel?

No hotel pickup is included; you meet at the waterfront departure point for check-in.

What landmarks will we see during this St. Augustine wine cruise?

You’ll see Castillo de San Marcos, Mission Nombre de Dios (the Great Cross), Flagler College, and more along the historic bayfront.

Are dolphins often spotted on this tour?

Dolphins are frequently seen but not guaranteed; birdlife is also common along the route.

Is food served during the wine tasting cruise?

No meal is included; only wine tastings are provided. Other drinks can be purchased onboard.

What should I wear for this St. Augustine bayfront cruise?

Secure footwear is required—no heels or flip flops—and bring a jacket for breezy evenings.

Is there an age requirement for this tour?

The minimum age is 21 years old due to alcohol service regulations.

What’s included

Your evening includes boarding at St. Augustine’s waterfront dock, a safety briefing by accredited crew, live local commentary throughout your bayfront cruise past historic sights like Castillo de San Marcos and Mission Nombre de Dios, plus guided tastings of six rotating wines—all taxes and fees are covered before you return to shore.