Top Orlando Wine Tasting Tours

Enjoy a pub crawl like no other in Winter Haven’s Chain of Lakes region. Meet your helmsman guide at the first stop, and order your first round of drinks. Then, hop aboard your pontoon with just a small group for company, and hit the water. You’ll travel by boat to four other popular bars and restaurants, and will have the chance to order drinks and bites at every stop (own expense).

A good choice for nature lovers, this tour takes you into a unique part of Rock Springs Run known as "Emerald Cut.” The first part of the tour is an upstream paddle through calm waters and overhead tree canopy, with stops to hop off your clear kayak and into the fresh spring water. Keep your eyes peeled for for fish, turtles, birds, small alligators, and more.

Orlando is full of pocket neighborhoods just outside of downtown. Discover Ivanhoe Village near the shores of Lake Ivanhoe and get a taste of the local cuisine. You and your local guide will visit five eateries, sampling foods like pizza and fried alligator bites. As you wander between restaurants, you’ll see some local boutiques which help foster this locally-owned community.

Winter Haven is a quaint city in Central Florida, known for its quiet canals and Chain of Lakes full of wildlife. And when you take this guided brunch tour, you’ll leave knowing that Winter Haven has quite the foodie scene, too. No chain restaurants or franchises on this tour, just award-winning local restaurants that residents love. Sip freshly roasted coffee, baked breads, and tasty cupcakes among the many brunch bites you’ll sample.

Get off the beaten path and try some great food while you’re at it with a visit to Orlando's Milk District, one of the best spots in town to sample delicious cuisine. On this small-group guided tour lasting about 3 hours, you'll try all sorts of food and drink as you learn about the Milk District—and Orlando overall—from your local guide.

There’s more to Orlando than theme parks. Discover the city of Orlando and the surrounding region on this sightseeing bus tour and optional boat cruise. Learn about the history of Orlando as you cover the downtown highlights around Lake Eola and browse the boutiques and specialty stores on Park Avenue. Upgade to a full-day tour to include a scenic boat ride through the lakes and canals of historic Winter Park, the self-proclaimed ‘Venice of America.’

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

Sanford sits just north of Orlando and is a favorite watering hole for locals who love a bit of history with their craft beer. This Sanford craft beer and history tour showcases the best of both. Stroll through this small city’s streets, uncovering facts about its history with prohibition. As you walk, you’ll pop into three local breweries for sips of their best beers.

Spend the morning birding in central Florida on this private half-day tour. Enjoy hotel pickup around the Orlando area or meet in Whittier. Hike and bird the Three Lakes WMA and Joe Overstreet Landing with a certified master naturalist, spotting species like Bald eagles, raptors, Painted Bunting, and Florida Scrub-jay.