Top 8 Wine Tours in St Augustine

Destination: St Augustine.
Ranked #8 in the U.S.A. on TripAdvisor, our award-winning Wine, Cocktail & Food Experience is the ultimate way to discover why St. Augustine was named Southern Living’s #1 Small Town Food City. In a relaxed, small-group setting, you’ll explore the city’s historic streets with a local guide who quickly becomes a new friend, stopping at some of our favorite restaurants, bars, and boutique spots along the way. Indulge in handcrafted cocktails, boutique wines, and dishes worth talking about, carefully selected to highlight the best flavors this foodie city has to offer. Each stop is thoughtfully chosen to complement the next, creating a journey of taste, story, and history. From savory bites to perfectly paired drinks, laughter to insider tips, this tour isn’t just about tasting, it’s about discovering the city through its flavors. By the end, you’ll understand why locals and visitors alike keep coming back.
Known For: St Augustine Half-day Tours, St Augustine Spring Break, St Augustine Wine Tours, St Augustine Wine Tastings, St Augustine Top Product, St Augustine Walking Tours, St Augustine Private and Luxury, St Augustine Food & Drink, St Augustine Excellent Quality, St Augustine Small Group.
Duration: Around 3 hours and a half.

Destination: St Augustine.
A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with four progressive style stops, each offering a seated tasting experience in one of our city’s hidden gems. From savory starters to sweet finishes, every course is paired with a boutique wine or artisanal cocktails. Bonus: arrive via the comfort of our chauffeured vehicle. Highlights: ELEVATED EXPERIENCE: Delve into St. Augustine's culinary scene with exclusive tastings at four top-tier venues. LOCAL INSIGHT: Benefit from insider knowledge shared by a local culinary guide. CHAUFFEURED COMFORT: Explore the city's charm in comfort aboard our open-air electric vehicle. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.
Known For: St Augustine Wine Tours, St Augustine Small Group, St Augustine Wine Tastings, St Augustine Top Product, St Augustine Private and Luxury, St Augustine Spring Break, St Augustine Golf Tours & Tee Times, St Augustine Half-day Tours, St Augustine Food & Drink, St Augustine Excellent Quality, St Augustine Culinary Tours.
Duration: Around 3 hours.

Destination: St Augustine.
A 'Progressive Style', Seated Food Adventure (Strolling): This tasting experience takes you to four handpicked venues — with each stop offering a dish featuring bold flavors, unique pairings, and unforgettable hospitality. From savory beginnings to sweet endings - you will enjoy one bite, one sip, and one story at a time. Highlights: CULINARY DELIGHTS: Each dish is thoughtfully paired with an exquisite wine or artisanal cocktail. INSIDER INSIGHTS: Get the scoop from a local culinary insider who'll be your guide throughout the journey. LEISURELY EXPLORATION: Stroll through St. Augustine's charming streets, soaking in its beauty and vibrant food scene, at casual pace. Note: Pairings are included. 24-HOUR ADVANCE NOTICE REQUIRED FOR ANY FOOD ALLERGIES. Age 21+ only. Sorry, NO pets of any kind. 4-person min to depart. Primary focus is on the culinary scene with a bit of history and sightseeing sprinkled in.
Known For: St Augustine Food & Drink, St Augustine Top Product, St Augustine Wine Tours, St Augustine Wine Tastings, St Augustine Small Group, St Augustine Culinary Tours, St Augustine Half-day Tours, St Augustine Excellent Quality, St Augustine Walking Tours.
Duration: Around 3 hours.

Destination: St Augustine.
Start your evening out by winding down on the water! Let us take you on an adventure to the bay-front, where our experienced guides will give you a tour on nature, wildlife, and famous historic landmarks. We are lucky to see a plethora of wildlife during this cruise including dolphin and birds like the famous Roseate Spoonbill! Remember, this entertaining cruise is during the sunset in the winter months, and in the early evening the rest of the year! You will receive a presentation and sampling of 6 fabulous wines (including local favorites) as we cruise past the famous historic bayfront. Our bar on board has an excellent variety of beer, wine, bubbly and soft drinks for purchase at very reasonable prices. There are no other tours like this in St. Augustine!
Known For: St Augustine Water Tours, St Augustine Spring Break, St Augustine Day Cruises, St Augustine Food & Drink, St Augustine Wine Tastings, St Augustine Top Product, St Augustine Likely to Sell Out, St Augustine Wine Tours, St Augustine Sightseeing Cruises, St Augustine Excellent Quality, St Augustine Likely To Sell Out.
Duration: Around 1 hour and a half.

Destination: St Augustine.
This is a food and wine tour that celebrates our history, today. Not only do we focus on local establishments to provide the best of the true St. Augustine cuisine, our licensed guides are fully knowledgeable in all aspects of our town's history. This will immerse our guests with an understanding of the people who have resided here throughout the ages as well as the food they've enjoyed. Wine or beer are provided with each food stop.
Known For: St Augustine Beer & Brewery Tours, St Augustine Wine Tours, St Augustine Half-day Tours, St Augustine Walking Tours, St Augustine Wine Tastings, St Augustine Food & Drink.
Duration: Around 3 hours.

Destination: St Augustine.
Toast of St. Augustine is a historic pub crawl based on the history of St. Augustine. Our licensed and certified guides will tell you thoroughly researched stories about the true history of St. Augustine. Our pubs are international and focus on the multi-cultural history of our city, including its beverages as well.
Known For: St Augustine Small Group, St Augustine Walking Tours, St Augustine Wine Tours, St Augustine Wine Tastings, St Augustine Excellent Quality, St Augustine Spring Break, St Augustine Food & Drink, St Augustine Beer & Brewery Tours.
Duration: Around 2 hours.

Destination: St Augustine.
Choose a narrated tour during the daytime or the Champagne Sunset Cruise option. From the sparkling midday waves to the golden hour glow, each tour provides a scenic view to witness the charm of America’s Oldest City. Cruise through the historic St. Augustine waterways, enjoying unobstructed, 360 degree, front-row views of the city’s most iconic landmarks. Our expert crew provides fascinating insights into 450 years of Florida history as pass the formidable coquina walls of the Castillo de San Marcos. Capture stunning photos of the Bridge of Lions from the water, catch a glimpse of the towering St. Augustine Lighthouse, and admire the Spanish Renaissance architecture of the downtown waterfront from a unique maritime perspective.
Known For: St Augustine Sunset Cruises, St Augustine New Product, St Augustine Private and Luxury, St Augustine Best Conversion, St Augustine Excellent Quality, St Augustine Food & Drink, St Augustine Water Tours, St Augustine Wine Tastings, St Augustine Top Product, St Augustine Catamaran Cruises , St Augustine Beer & Brewery Tours, St Augustine Wine Tours.
Duration: Around 1 hour and a half.

Destination: St Augustine.
St. Augustine Mobile Wine Tasting Tour: Sip, Savor & Explore Experience the charm of St. Augustine like never before with our exclusive Mobile Wine Tasting & Food Pairing Tour. Perfect for wine enthusiast and curious newcomers, this intimate, chauffeur-guided experience blends indulgence, education, and scenic exploration. What to Expect Glide through historic streets of St. Augustine in a quiet, eco-friendly vehicle while enjoying curated wine tastings, gourmet charcuterie pairings, and personalized service. Ideal for couples, friends, or small groups (up to 12). Call larger groups 877-4-WINETOUR Tour Highlights: •Downtown Parking for a hassle-free start. • Concierge-Style Guidance • Exclusive Tastings with charcuterie & dessert. • Scenic Views of St. Augustine’s landmarks. • Inspiring Atmosphere with soft music & great conversation. • History & Wine Education from expert guides. • Handpicked Stops at top local venues. Uncork an unforgettable journey in the Nation’s Oldest City!
Known For: St Augustine New Product, St Augustine Spring Break, St Augustine Private Sightseeing Tours, St Augustine Food & Drink, St Augustine Wine Tastings, St Augustine Golf Tours & Tee Times, St Augustine Wine Tours.