Top Florida Wine Tasting Tours

Sail along St. Augustine’s picturesque coastline—and indulge in a number of generous wine samples—during this two-in-one tour. Make your own way to the dock, hop aboard the pontoon boat, and get comfortable: as you set off, you’ll see landmarks like the Castillo de San Marcos, the Bridge of Lions, and more. You’ll also taste six different wines, and will have access to the on-board bar.

Want to eat out during your trip to St. Augustine, but not sure where to go? Get acquainted with the city’s wine and food scene during this St. Augustine Food, Wine, and Cocktail Tour. Go to some of the most unique spots in the city to grab a bite and an alcoholic beverage in the afternoon, one of the best times to explore, with a guide who knows the city’s history well.

Take a tour of one of Florida's handful of wineries on this excursion in Clearwater. Follow your guide through a tour of the winery whilst you learn about wine production methods. Then, enjoy a tasting of three onsite-produced wines. Nibble charcuterie as you go to keep your palette neutral so you are able to pick up on the unique flavor profiles.

If you’ve got an appetite for experiencing the best food and wine St. Augustine has to offer, then grab a bib and a comfortable pair of walking shoes for this unique foodie tour. Corks and Forks is a food and wine pairing tour that’ll introduce you to the tasty side of America’s Oldest City. Sample local cuisine and delicious wine while strolling through the Historic District.

Enjoy a memorable evening on the water with Keylypso's Craft Beer & Wine Sunset Cruise. Glide along the Intercoastal as the sun sets over Palm Beach, providing stunning views of Peanut Island and luxurious waterfront estates. Sip on an array of craft beers and wines while relaxing in a spacious covered seating area. Soft music enhances the ambiance as you create unforgettable memories with friends or that special someone. This 2-hour cruise is perfect for any occasion, making it an ideal way to unwind and appreciate the beauty of Florida's coastline. - Duration: 2 hours of relaxation on a spacious catamaran - Enjoy craft beer, wine with great company - Maximum capacity of 34 guests for an intimate experience - Witness breathtaking views of the sunset and coastal scenery

A delicious tour of America’s Oldest City awaits you on this chauffeured food and wine tour through St. Augustine. This auto-adventure whisks you through the streets of St. Augustine’s historic district in an open-air electric vehicle, stopping at some of the guide’s favorite dining venues. Local cuisine paired with tasty wines await your taste buds. As you ride along the streets, pass Flagler College, the Huguenot Cemetery and other historical landmarks.

You will hear firsthand accounts of murders and other serious crimes that have occurred over time, all within and around the Tampa Bay area. Your tour guide has over three decades solving crimes and making arrests in the Tampa Bay area. This is not like other tours because you will hear inside details of the information that was not disclosed to the public and press. Get ready to put your detective skills to use. Your guide will take you to hidden gems that only locals know about. You will laugh and cry and have an adventure that is so much fun, it’s criminal. Rain or shine, the mystery awaits you. Come step on board and prepare for a day of nonstop intrigue. The Wine and True Crime tour is a perfect way to celebrate a birthday, girls’ night out, Bachelorette Party, Divorce Party or any other celebration!

Cruise along Fort Lauderdale’s historic New River and enjoy a delicious barbecue dinner on this cruise. Board the Jungle Queen Riverboat and see the luxurious mansions and yachts along Millionaire’s Row, stretching from the Bahia Mar Yachting Center to the Intracoastal Waterway. The cruise travels to a tropical isle for an endless dinner offering barbecue ribs, and chicken with all the trimmings. Then experience a laugh-out-loud variety show to cap off an enjoyable and entertaining evening.

Explore the Tampa, Florida bar scene from the comfort of a street-legal golf cart and a driver to help you get around with ease. From Downtown Tampa to the hip Channel District to Tampa Heights, and more, let your tour leader show you some of the best spots in the city. If you’d like to lean into a specific vibe, just let your guide know.

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!

Explore the Florida Everglades on an airboat adventure and wildlife encounter at Sawgrass Recreation Park. This exciting airboat ride is a great way to experience the unique subtropical ecosystem of the Everglades. Skim across the water at high speeds while looking for alligators, fish, turtles, and wading birds. This guided tour includes admission to Sawgrass Recreation Park, a ticket to the alligator and reptile exhibit, and a guided airboat tour.

See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar with the Osprey, 21 and older option, or select the Island Breeze option for a family-friendly experience.

Perfect for those who want to squeeze a lot of sightseeing into a limited amount of time. A fully narrated 90-minute cruise along the New River through Fort Lauderdale will let you soak up such sights as the lavish homes and mega yachts along Millionaire's Row.

Step aboard an evening cruise for dinner and drinks while you take in views of St Pete Beach. Watch over the landmarks of St Petersburg and fill up on food from the tropical-themed buffet. An open bar means you won't go thirsty while jamming to island music from the onboard DJ and other entertainment.

Enjoy a comfortable and flexible way to explore the best of St. Augustine on this narrated Old Town trolley tour. See dozens of points of interest, such as the Old Jail, Flagler College, and Spanish colonial neighborhoods. Along the way, discover more about America’s oldest city, founded in 1565, from your conductor, and listen as they share in-depth narration about St. Augustine's history.

Eat your way through the many flavors of South Beach—and immerse yourself in the area's vibrant culture—on this two-in-one, small-group walking tour. Accompany your guide to local restaurants and foodie hideaways that you'd likely otherwise miss. Along the way, learn about the commingling of cultures that defines this diverse Miami neighborhood, and spot some of South Beach's iconic art deco architecture, too.

Experience the sights and sounds of Miami’s vibrant Little Havana neighborhood on this guided walking food tour. Explore this lively Cuban district and discover its fascinating history and culture, with stops at some of the best family-owned and operated Cuban restaurants in the area. Sample the local cuisine, like guava pastries, chicken plantain cups, and flan ice cream. Also, meet some of the local artists, watch skilled Cuban cigar rollers and listen to traditional Cuban music.

Hop onboard the air-conditioned trolley with Owner Tammy for a fun trip with singing and wine trivia to visit your own Fiorelli Vineyards for wine tasting, live music, lunch and a tour. Learn about the wine made at Fiorelli, sample 6 of their local wines and add on a lunch option (Caprese Salad, Italian Panini or Charcuterie Board) to eat while you enjoy the music in the gardens. Shop in the gift shop and bring home your favorite wine. Enjoy singing along to wine-inspired songs on the way down and back.

Discover the soul of Spain through six Mediterranean wines from Valencia, authentic pairings with traditional Spanish Tapas and unforgettable stories.

Savor the Flavors of Downtown Tampa’s Riverwalk! Embark on a 3-hour walking food and wine tour through downtown Tampa and the scenic Riverwalk. Enjoy a culinary journey as we visit 4 to 5 top restaurants, each showcasing their finest tastings, paired with three handcrafted beverages. Our tour blends rich history, cultural gems, and stunning waterfront views, creating the perfect backdrop for an unforgettable experience. Tampa’s vibrant cuisine is as diverse as its culture—come indulge in this one-of-a-kind foodie adventure filled with delicious bites, refreshing drinks, and the city’s iconic charm. We can’t wait to share it with you!

This Wine Wednesdays experience offers a cost-effective way to explore quality wines without weekend crowds. Guests gain practical wine knowledge through sommelier guidance, helping build confidence when choosing wines independently. The midweek schedule allows easier booking and a more relaxed pace, making it ideal for after-work plans. The experience is available in English and Spanish to accommodate more guests.

Discover the vibrant craft beer scene of Orlando on this brewery tasting tour. Visit three local breweries, including Sideward Brewing, Rockpit Brewing, and Windermere Brewing Company, where you'll savor three unique flights of beer. This tour offers insights into the brewing process and the chance to meet local brewers. Perfect for beer enthusiasts and anyone looking to explore Orlando's craft beer culture. Enjoy a casual atmosphere, and don’t forget to hydrate with complimentary bottled water throughout the tour. - Tour duration of approximately 4 hours, starting at 11:30 am - Sample 3 flights of beer, with insights from knowledgeable guides - Maximum group size of 10 to ensure an intimate experience - Convenient meeting point on International Drive behind Yard House

Explore Jacksonville's vibrant San Marco neighborhood on the Savoring San Marco Food Tour, the city's first food tour that showcases a delightful array of local cuisine. This culinary adventure leads you through five carefully selected stops, where you'll enjoy an assortment of mouthwatering appetizers and desserts while learning about the area's rich history. Perfect for locals and visitors alike. Expect a memorable experience that blends flavors with community insights, all while strolling through charming streets. - Journey through five unique stops in San Marco’s culinary landscape - Savor a variety of delicious dishes from local eateries - Enjoy complimentary bottled water during the tour - Ideal for food enthusiasts and those curious about Jacksonville's heritage While individual bookings are welcome, please note that tours require a minimum of two guests. If you are the sole participant, we will either reschedule your experience or provide a full refund.