St. Augustine wine and food tour: Historic streets, local guide

Three and a half hours of cocktails, wine, and food across St. Augustine's oldest streets

A wine, cocktail and food tour through St. Augustine's historic district with a local guide, stopping at restaurants and boutique spots to taste handcrafted drinks and carefully selected dishes. The tour lasts three and a half hours, includes bottled water and lunch, and is limited to small groups; minimum age is 21. Non-alcoholic drinks are available on request.

Step-by-step itinerary

Explore St. Augustine's historic sites and flavors

• Enter through Old City Gates
• Walk along St. George Street
• Visit Castillo de San Marcos fort
• See St. Photios Greek Orthodox Shrine
• Stop at Huguenot Cemetery
• Explore Town Plaza and Government House
• View Cathedral Basilica of St. Augustine
• Enjoy wine, cocktails, and food tastings

The Experience

The tour starts on St. George Street, the backbone of St. Augustine's historic district, and moves through the oldest parts of the city. You'll pass the Old City Gates (built in 1808), the Huguenot Cemetery, and the St. Photios Greek Orthodox National Shrine before reaching the Town Plaza, where the Cathedral Basilica and Government House anchor the original 1573 city plan. The Castillo de San Marcos, a 325-year-old Spanish stone fortress and the oldest masonry fort in the continental United States, sits nearby. Each stop is chosen to flow into the next, so the geography itself becomes part of the story.

At each restaurant and bar along the way, you'll taste handcrafted cocktails and boutique wines paired with dishes the guide has selected to show off what makes St. Augustine a foodie destination. The pairings build on each other—savory bites complement the drinks, and the sequence matters. Bottled water comes with you, and lunch is included. If you prefer non-alcoholic drinks, the guide can arrange them. The guide is a local who knows the city's flavors and its history, and the group stays small enough that conversation happens naturally.

The tour is ranked #8 in the U.S.A. on TripAdvisor and reflects why Southern Living named St. Augustine the #1 small town food city. It's not a lecture about the buildings you pass—it's a walk through the city's streets with someone who lives there, stopping to eat and drink at places that matter to locals.

What’s included

• Bottled water.
• handcrafted cocktails and boutique wines at each stop.
• lunch.
• a local guide who speaks English.
• small-group setting on historic St. Augustine streets.

Good to know

Moderate physical levelWheelchair accessiblePets welcomePublic transport nearbyNot for heart conditionsNot for back problems

Operated by St. Augustine Experiences

Is this one for you?Choose this if you want a local guide setting the pace and selecting restaurants for you—you follow the commentary rather than plan the route yourself.

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Top questions

What is the Castillo de San Marcos and why does it matter to St. Augustine?

The Castillo de San Marcos is a 325-year-old Spanish stone fortress built in the 17th century to protect Spain's claims in the New World. It's the oldest masonry fort in the continental United States and a National Monument, sitting at the edge of the historic district you'll walk through on the tour.

How much walking is involved in this tour?

The tour covers St. Augustine's historic streets and lasts three and a half hours. You'll move between restaurants, bars, and historic sites on foot, so a moderate level of physical fitness is needed. The route is wheelchair accessible, and public transportation options are available nearby if you need them.

Can I do this tour if I don't drink alcohol?

Yes. Non-alcoholic drinks are available on request, and the guide can arrange them at each stop. You'll still taste the food pairings and get the full tour experience.

What dietary restrictions can the tour accommodate?

The tour includes lunch and food tastings at each stop. Vegetarian, vegan, kosher, dairy allergy, sugar-free, and gluten-free options will have a much more limited selection at the restaurants, so let the operator know in advance if you have restrictions.

Is there a minimum age for this tour?

Yes, the minimum age is 21 because the tour includes alcoholic beverages at multiple stops.

What's included in the price?

Bottled water, lunch, and all the handcrafted cocktails and boutique wines at each stop are included. Gratuities are not included.