St. Augustine Wine, Cocktail, & Food Experience

Small Group Sizes

Savory wines and handcrafted cocktails

Food pairings at each location

The Perfect Pairing Experience blends wine, cocktails, food, and history to create an incredible afternoon for your family and friends. Take in the picturesque streets and architecture between sipping on colorful cocktails, enjoying cheese & charcuterie, and dining on cuisine inspired by some of our chefs’ travels.


Small Groups Guaranteed!

Lots of food!

Great for birthdays, bachelorettes, and team building!

The Perfect Pairing is the PERFECT holiday gift! Gift certificates never expire!

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Trip Details


Public Tour: $139 per guest

We recommend all guests be 21+ to join this tour. Mocktails and non-alcoholic drinks available for underage guests and non-drinkers.

Departure Time

2:00 PM, Wednesday – Monday, rain or shine

Meeting point

Right in the heart of the historic district on Treasury Street. After your reservation is made, you will receive a confirmation message with maps and exact address of our meeting location

Ending Point

On Aviles Street near Plaza de la Constitución


Wednesday – Monday, year-round, except for major holidays and special events in downtown St. Augustine. Please check our calendar for availability.


Approximately 3 1/2 hours

Group size

All public tours are semi-private with 8 people or less.

Participation Requirements

Must be 21+ years of age for wine and alcoholic cocktails. Mocktails and non-alcoholic drinks available for underage guests and non-drinkers. It is a walking tour, but the pace is slow and comfortable.

We recommend your most comfortable walking shoes as we will be walking on old and sometimes cobblestone streets.


  • Wine tasting and charcuterie at first stop
  • Choice of wine or cocktail at second and third stops
  • Food pairings included at second and third stops (vegetarian option available)
  • Water provided between stops

What to bring

Valid US ID or passport (for international guests), as we will be checking them before the tour. You do not need any printed tickets. Otherwise, wear comfortable walking shoes and bring your enthusiasm for wine, cocktails and food!


Vegetarian option is available, please advise at time of booking if required. Any other dietary needs cannot be accommodated on this tour (vegan, kosher, nut allergies, dairy-free or gluten-free diets)

Overview of Your Tour

A visit to St. Augustine should start with our Perfect Pairing Experience. Located in the beautiful downtown historic district, it’s the perfect way to immerse yourself in St. Augustine’s eclectic culinary scene.

We stop at 3 of the city’s best venues for imbibing with friends in America’s oldest city. Savor wine tastings, charcuterie boards, colorful cocktails and cuisines. Between delicious drinks and food, view sites such as the Old City Gates, our famous Castillo de San Marcos, Plaza de la Constitución, and America’s oldest thoroughfare, Aviles Street. Our Perfect Pairing Experience lets your group explore the picturesque alleys and architecture of charming St. Augustine.

Frequently Asked Questions

We recommend that guests be 21+ to full enjoy the tour. Underage guests can join, but there is no price difference for ordering mocktails and other non-alcoholic drinks.

The tour lasts about 2.5 – 3 hours, but we will only cover about 0.7 miles of total walking at a relaxed pace.

All tours are held rain or shine. However, we supply ponchos if it rains. We recommend you check the weather forecast to help you choose your shoes and garments and bring an umbrella.

Bartender/server gratuities are already included in the tour price.

While it’s never expected, if you enjoyed your tour and want to give a tip to your tour guide, please do! Most guidebooks and American Express suggest 20% of the full tour price. There is even an option to tip your guide while booking a tour.

The wine tasting at our first stop has been hand picked by their expert team. If you have any allergies to specific wines please let us know and we can substitute. We will have our recommended wines/cocktails at the second and third stop, but you can choose any drink you like from their menus.

Have more questions? Check out our FAQ page!