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Captivating Fall Magic in St. Augustine

Are you prepared to embark on an extraordinary seasonal journey through St. Augustine, where captivating tastings and immersive tours await?

As the vibrant hues of summer begin to fade, a new enchantment takes hold in St. Augustine, Florida. Known for its rich history, cobblestone streets, and centuries-old architecture, this coastal gem transforms into a haven of fall splendor as the temperatures dip and the foliage takes on a golden hue. Settled by Spanish explorers in 1565, St. Augustine 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 tasting tours the city hosts today. Step into a world where history and nature converge in a dance of colors and experiences, making autumn in St. Augustine a truly unique and captivating time to visit.

Want to taste a little Minorcan heritage? Many restaurants serve Minorcan clam chowder and St. Augustine relishes the fiery datil pepper, it's as hot as a habanero. While not from Minorca, the Minorcans adopted it centuries ago as their own and use it in a variety of recipes. St. Augustine has a Datil Pepper festival annually in October and many shops sell datil pepper products.

While strolling the narrow streets of St. Augustine you'll find yourself immersed in a tapestry of historic sites, charming boutiques, and inviting cafes. The crisp air carries a sense of nostalgia as you explore the cobbled lanes, where centuries of stories are etched into the very stones beneath your feet. The scent of pumpkin-spiced treats wafts from local bakeries, inviting you to indulge in the flavors of the season.

Embrace the coastal charm as you take in breathtaking views of the Atlantic Ocean. A visit to Anastasia State Park reveals a natural sanctuary, where you can meander through trails blanketed by fallen leaves, savoring the tranquility of the season. Feel the sea breeze on your skin as you stand atop the historic St. Augustine Lighthouse, marveling at the panoramic vistas that stretch as far as the eye can see.

Indulge in fall flavors at local eateries, where chefs showcase the region's bountiful harvest in their culinary creations. From fresh-caught seafood to farm-to-table delights, your taste buds will be treated to a symphony of flavors that perfectly complement the season.

Whether you're sipping spiced cider by the waterfront, discovering hidden courtyards adorned with pumpkins, or relishing in the magic of illuminated evenings, autumn in St. Augustine is an invitation to slow down, savor, and connect with the timeless charm of this historic city. So, as the leaves begin to fall and a touch of chill lingers in the air, make your way to St. Augustine and immerse yourself in the splendor of fall's embrace in this captivating coastal haven.

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 food and wine experiences in our “Nation’s Oldest City” and find out why it was named the #1 Foodie Town by Southern Living magazine.


Full disclosure we receive an affiliate commission for the tastings & tours below.

St. Augustine's Wine, Cocktail and Food Experience

Wander the historic streets & picturesque alleys of America's oldest city, St. Augustine. Enjoy wine tasting, 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 wine, cocktail & food-filled three-and-a-half-hour tour meets up at the courtyard of Casa de Vino 57 at the bar. Tour start at 2 PM.

Corks and Forks Culinary Tour

Voted the "BEST food and wine pairing tour" by Travel & Leisure Magazine! On this 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.

"Rachael was a fantastic guide - knowledgeable, attentive and all around fun. This tour is a great way to see highlights of St Augustine. The food and wine stops were great and we had plenty to eat and drink. Highly recommend for a girls weekend or couples." James

Wine Tasting Cruise in St. Augustine

See America's oldest city in a new light by making your way to the dock to hop aboard the sightseeing and wine pontoon boat. While aboard you will taste six different wines, and learn about what makes them special while keeping your eyes out for wildlife.

“What a fun cruise! Crew was great! Beautiful evening for cruising, seeing the sights of St. Augustine from the water, observing lots of dolphins, and of course, enjoying some wine!” Elizabeth

Enjoy views of the beautiful Bridge of Lions, Castillo de San Marcos National Monument and the National Shrine of Our Lady of La Leche at Mission Nombre de Dios.

Get a Pirate's view of the Flagler College and how it looks from the water making up the city's skyline while soaking up the sun on this one in half hour cruise!

The Feast of Saint Augustine

This "Viator 2022 Winner" three hour walking 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.

"This was an enjoyable walking tour with delicious food and wine. Not only informative but fun as well!! Highly recommend for anyone wanting a great time while experiencing local restaurants." Dawn

Not Just A Chocolate Tour

Discover 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.

The one in half hour tours starts at the Ancient City Brunch Bar where you will meet your guide at 10:30 AM.

Wine & Dine Culinary Tour

This will have you rolling the city streets in an open aired vehicle. 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.

"Awesome experience!! Corley was a fantastic guide & took us on a great tour around the city & across the Bridge of Lions! The chef & her assistant were fabulous & gave us lots of great information & recipes! The wine pairing & charcuterie at the Treasury Building/ culinary office was our favorite part of the tour....& the views of the city were beautiful! We highly recommend this experience!" Kelly

Ale Trail Craft Beer Tour

Visit breweries and bars to sample the best of St. Augustine's craft beer as you discover the historical highlights of one of America's oldest cities on this immersive tasting tour.

Meet your tour guide inside the first brewery on this three hour tour before strolling the historical streets to discover the history of a 1790 Coquina House and find the narrowest street in the city.

So, until we gather again to explore new tastes and create new memories, raise your glass to the season, to the flavors, and to the magic of St. Augustine. Cheers to fall, to friends old and new, and to the endless possibilities that lie ahead on our culinary journeys. As you wander these historic streets, remember that every bite is a chapter in the tale of your time here, and every sip is a toast to the unforgettable moments that make life truly delicious. Discover more Tasting Tours in St Augustine! Start planning your getaway to St. Augustine, Florida today.

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