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).

There’s more to Orlando than theme parks. Discover the city of Orlando and the surrounding region on this full-day sightseeing bus tour and boat cruise. Learn about the history of Orlando. Enjoy a scenic boat ride through the lakes and canals of historic Winter Park, the self-proclaimed ‘Venice of America.’ See the downtown highlights around Lake Eola and browse the boutiques and specialty stores on Park Avenue. Select Orlando area pickup and drop-off included.

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.

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, you'll try all sorts of food and drink as you learn about the Milk District—and Orlando overall—from your local guide.

Icon Park, on International Drive, is home to some of Orlando’s best restaurants, and with this gastronomic tour, you can taste your way around the park. Led by a guide, enjoy commentary about the local area, and stops for a variety of food and drink specialties.

International Drive is the epicenter for evening entertainment in Orlando’s tourist district and there are few better ways to spend the night than enjoying dinner and a show. This ticket is your reservation for dinner and a show at Mango’s Tropical Cafe, an award-winning nightclub. Evoking the fun of 1930’s New York and the flair of the Tropicana in Havana, Cuba, your night at Mango’s will have you singing and dancing long after dinner ends.

Spend the morning birding in central Florida on this private half-day tour. Meet in Whittier or enjoy pickup from around the Orlando area. Hike and bird the Three Lakes WMA and the Joe Overstreet Landing with a certified master naturalist, and look for and learn about species such as Bald eagles, raptors, Painted Bunting, Florida Scrub-jay, and more.

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.

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.

Have you ever taken a wine tasting class? Do you love Michelin Chef-prepared meals? Well, then we have you covered! Join us downtown and experience our chef's table tour! (Includes Charcuterie, Wine Tastings, & 3-course pre-fixe farm to table dinner)