St. Augustine: Food & Wine Walking Tour with Pairings

Summary

St. Augustine flavors meet stories on a relaxed city food adventure

You’ll wander St. Augustine’s historic streets, tasting bold dishes paired with local wines or cocktails at four handpicked venues—all guided by someone who knows every story behind each bite. Expect laughter over shared plates, a bit of history sprinkled in as you pass landmarks like Governor's House, and that feeling of being truly welcomed into the city’s food scene.

What’s the experience like?

Someone’s pouring a deep red into my glass before I’ve even sat down—turns out, that’s just how they do it here in St. Augustine. Our guide, Jamie, grinned and nudged me toward the window seat (“best people-watching in town,” she promised). The first bite was this flaky pastry with something smoky tucked inside—I should’ve asked what it was, but honestly I was too busy trying not to drop crumbs all over the tablecloth. There’s this faint scent of old wood and citrus in the air, which somehow makes everything taste brighter.

We strolled between stops—four places in total, all within these winding streets that feel like they’re holding their breath between centuries. At one point we passed the Governor's House Cultural Center and Museum; Jamie paused to tell us how it’s watched over the plaza since 1598 (I tried to imagine that many years stacked up—couldn’t quite manage it). The second venue had a cocktail with rosemary that made my fingers smell like Christmas for the next hour. I asked our server if that was intentional and he just winked.

By the third stop, everyone at our table was swapping stories about hometown foods—weirdly comforting when you’re sharing plates with strangers. Someone mentioned how “progressive style” meant we’d get to sit at each place instead of eating on the go, which honestly made all the difference for me. Dessert came last (of course), something creamy with berries, and I caught myself wishing I could pocket that last spoonful for later. Walking back through St. Augustine’s streets after three hours of food and wine felt like floating—maybe from the wine, maybe just from being full in every sense. Still thinking about that rosemary cocktail.

Step-by-step itinerary

Day 1 — St. Augustine food and history tour

• Meet licensed culinary tour host
• Stroll through St. Augustine streets
• Visit four to five handpicked venues
• Enjoy food and wine pairings at each stop
• Learn history of Government House site
• Explore Town Plaza and harbor views

Top questions

How long is the St. Augustine food & wine tour?

The tour lasts approximately 3 hours.

How many venues are included on this day trip?

You’ll visit 4 handpicked venues during the experience.

Is transportation included in this St. Augustine food tour?

Private transportation is included as part of your booking.

Are alcoholic beverages part of the tour?

Yes, wine pairings or artisanal cocktails are included at each stop.

Is this walking tour wheelchair accessible?

Yes, the tour is wheelchair accessible.

Can dietary restrictions be accommodated?

Severe life-threatening allergies must be noted 24 hours in advance; other restrictions cannot be guaranteed.

What is the minimum age for this food & wine tour?

The minimum age is 21 years old.

Are pets allowed on this culinary adventure?

No pets are allowed on this tour.

What landmarks will we see along the route?

You’ll pass by sites like Governor's House Cultural Center and Museum during your stroll.

What’s included

Your day includes private transportation between stops, all food tastings paired with local wines or cocktails (beer available by request), a knowledgeable local guide leading you through four venues across historic St. Augustine, plus dessert to finish—basically enough for a generous lunch or dinner before heading home satisfied.