Dining At Twilight: An Evening Culinary Experience

Small Group Sizes

Food, Wine, History & more!

Explore the unique character of this city

Our Dining At Twilight Experience blends wine, food, and history to create an incredible evening on the town for your family and friends. Come explore 3 of our favorite drinking & dining establishments on this progressive dinner tour.


Small Groups Guaranteed!

Come hungry! There is lots of food!

Great for birthdays, bachelorettes, and team building!

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Trip Details


Public Tour:

$159 per guest.

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

Departure Time

6:00 PM, Wednesday & Saturday only*, rain or shine

*Groups of 4 or more please call if you are looking for a different evening for a private tour

Meeting Point

Treasury Street near Cordova Street. After your reservation is made, you will receive a confirmation message with maps and exact address of our meeting location.

Ending Point

On Cordova Street near the Historic Parking Garage


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


Approximately 3 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 beer. 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 beer with dinner at second stop
  • Choice of wine with decadent dessert at third stop
  • 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

Everybody should enjoy a stress free evening out on the town! Relax and let our team curate a memorable evening of culinary delights and history. Imbibe on boutique wines in our favorite backyard. Savor French dishes such as escargot and foie gras. Wear comfortable pants as our decadent dessert is way over the top! You need to see for yourself why Southern Living Magazine named St. Augustine the #1 dining city in the South!

Come eat, drink, learn, and laugh with us! We hope to see you soon!

Frequently Asked Questions

We recommend that guests be 21+ to fully 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 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 to see if you’ll need 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. Guests will have a choice of wine selected by the owners at the second & third stops.

Have more questions? Check out our FAQ page!

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