St. Augustine’s rich heritage makes the city and its surroundings a unique getaway, but did you know it’s also a foodie paradise with a burgeoning dining scene, which certainly adds to the romance of this magical place.

Settled by Spanish explorers in 1565, it has also been home to many cultures including Native American, Greek, Minorcan, French and British, which influences everything from food to architecture, shopping to entertainment and the many festivals and special events the city hosts year-round.


While strolling the narrow streets of St. Augustine get transported to a Spanish courtyard to sip wine at Bin 39 Wine Bar, located in the lobby of the St George Inn at the North end of the pedestrian-only street. Spanish Street is home to Southern cuisine and an always changing menu, the Floridian , is one of St Augustine's finest farm to table restaurants and tucked away on a side street in the Historic District, tiny Cousteau’s Waffle & Milkshake Bar  is a veritable graveyard for New Year’s resolutions. With a Belgian Liege Waffles & Milkshake packed menu its best savored with a long stroll through the Ancient City.

One of the best ways to taste the place with one of the annual Food & Wine Festivals. Showcasing Spanish wine, cuisine and culture the annual St. Augustine Spanish Food & Wine Festival is held in February, but if you cant make it than, no worries ... St. Augustine Food + Wine Festival , named “One of Florida’s Top 10 Food & Wine Festivals” by USA Today is right around the corner in May and showcases culinary, beverage and culture that highlights St Augusine's celebrity guest chefs, local chefs, celebrity winemakers/proprietors, artisans, farmers, local craft spirits and beers, along with renowned wine, spirits and beer brands from around the globe.

Another fun way to taste the place, if you have never been, is by taking a tasting tour with an expert who knows the history, the hidden courtyards and the “best of” that St. Augustine has to offer.

Come along with us as we share some of our favorite 5 star Tasting Tours in our “Nation’s Oldest City” and find out why it was named the #1 Foodie Town by Southern Living magazine.


If you choose one of the first four tours you’re going to want to grab your walking shoes. The first of our walking tours is The Feast of Saint Augustine. This three hour tour will have you traveling from St. George Street to the Bayfront, to the historic Spanish district and the Flagler Model Land Project all while enjoying the unique tastes of the city. Experience an olive oil tasting, taste local farm to table cuisine while supporting local growers and producers, enjoy wine tasting in the historical district and indulge in Mediterranean food along Cathedral Street.

Our second walking tour is St. Augustine's Wine, Cocktail and Food Experience where you will explore the picturesque alleys and architecture of charming St. Augustine while Savoring wine tastings, charcuterie boards, colorful cocktails and cuisines. Between delicious drinks and food, view sites such as the Old City Gates, the famous Castillo de San Marcos, Plaza de la Constitución, and America’s oldest thoroughfare, Aviles Street.

The third of our walking tours is voted the "BEST food and wine pairing tour" by Travel & Leisure Magazine! On the Corks and Forks Strolling Tour , you will sip and savor your way through the city on this decadent food and wine tasting tour, following an entertaining guide on an epicurean journey of discovery. Three hours and five pairings on the menu, guests will be treated to a selection of dishes that represent the best of St. Augustine, matched with local and regional wines that complement the flavors.

The fourth and last of our walking tours will have you discovering the sweeter side of this pedestrian friendly city on the St. Augustine's Not Just A Chocolate Tour. Indulge in the sweeter things in life with customized lattes, some of the best chocolate and sweets St. Augustine has to offer. Wander through the old brick street of the Ancient City while getting to know the little brunch shops, candy stores and bakeries along the way. Remember your experience with a gift bag of treats to take home with you.

Our last and final 5 star tour will have you rolling the city streets in a roadster named “Roxanne”. The Wine & Dine Rolling Tour takes you to five beautiful venues from fine dining to a popular sweet dessert bar. Enjoy mouthwatering food and wine tastings, tea at a little tea shop and end with a sweet treat that will tantalize your taste buds and leave you wanting more on this three hour tour.

Discover more Tasting Tours in St Augustine! Start planning your getaway to St. Augustine, Florida today.

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