St. Augustine: Sweets & History Walking Tour with Tastings

Summary

Chocolate meets centuries-old plazas on this St. Augustine walk

You’ll taste chocolate and pralines in St. Augustine’s historic heart, wander past centuries-old plazas with a local guide, hear quirky stories behind city landmarks, and leave with extra treats to enjoy later. Expect laughter, unexpected history lessons, and that feeling when you realize you’re part of the street’s story for an afternoon.

What’s the experience like?

"Try this one—it’s the real deal," our guide grinned, holding out a tiny cup of thick drinking chocolate right there in the middle of St. George Street. I’d barely swallowed my first sip when the smell of pralines drifted over from the next shop, all sugar and toasted pecans. The sun bounced off those old coquina walls and I remember thinking, wow, people have been snacking around here for hundreds of years.

We wandered past the Governor’s House—honestly, I didn’t expect to care about a courthouse, but our guide made it sound like a soap opera with all those Spanish and British governors swapping places. There was this bit where she pointed at a weathered stone plaque and told us about the city plan from 1573—how plazas had to start at the waterfront so everyone could see who was coming in by boat. It felt kind of wild, standing there with chocolate on my fingers while imagining Spanish ships gliding into Matanzas Bay.

The Cathedral Basilica bells chimed while we tasted something called “turtle” (not actually turtle, thank god—just caramel and pecans). I tried to pronounce “praline” like our guide Li did—she laughed and said I sounded French-Canadian instead of Floridian. The group was small enough that we all swapped stories about our favorite sweets back home. Someone mentioned their grandma’s fudge recipe; suddenly I missed mine too.

I left with a little thermal bag full of goodies for later (the nutty ones were my favorite), but honestly it’s the mix of old stones, sweet smells, and random laughter that stuck with me more than any single bite. Sometimes you just need an afternoon wandering somewhere sticky-fingered and curious—you know?

Step-by-step itinerary

Day 1 — Explore St. Augustine's sweets and history

• Visit Government House Cultural Center
• See historic Town Plaza park
• Pass by former Ponce de Leon Hotel
• Tour St. George Street vendors
• View Cathedral Basilica of St. Augustine
• Stop at St. Photios Greek Orthodox Shrine

Top questions

How long is the St. Augustine sweets & history walking tour?

The tour lasts approximately 2-3 hours as you stroll through downtown St. Augustine.

Are food allergies accommodated on this chocolate tour?

The tour can only accommodate nut-free options on the Not Just a Chocolate Tour; other dietary restrictions like vegan or gluten-free cannot be accommodated.

Is this walking tour wheelchair accessible?

Yes, the tour is wheelchair accessible throughout historic downtown St. Augustine.

What is included in the sweets & history walking tour?

The tour includes bottled water, tastings at each location, coffee or tea at the start, plus treats to take home in a thermal bag.

Where does the tour start in St. Augustine?

The exact starting point is provided after booking; it begins in historic downtown near major landmarks like Government House.

Can infants or small children join this walking tour?

Yes, infants and small children can ride in a pram or stroller during the tour.

Does the tour include any historical sites?

Yes, you’ll pass by sites like Governor's House Cultural Center & Museum and Cathedral Basilica during your walk.

What’s included

Your afternoon includes coffee or tea to kick things off at your first stop, bottled water along the way as you wander through downtown St. Augustine with your guide, sweet tastings at every location (think chocolate and pralines), plus a little thermal bag packed with extra goodies to bring home for later.