Orlando might be famous for theme parks and sunshine, but it’s also surprisingly good for drinking tours. Unlike larger cities, Orlando offers a range of unique ways to explore its local bar scene and natural surroundings. Whether you want to cruise on a pontoon boat, sample craft beers in historic towns, or uncover spooky stories over drinks, you’ll find options that suit different tastes and group sizes. Many tours feature small groups, knowledgeable guides, and authentic experiences that go beyond just visiting bars—they highlight local wildlife, history, and even some ghostly tales. If you’re looking to combine relaxing scenery with social fun, these tours are worth considering.
And no matter which experience catches your eye, booking in advance is wise—these tours tend to fill up fast, especially during peak seasons. This guide will help you pick the best drinking tour in Orlando for your style, whether it’s a lively pub crawl on water, a scenic paddle with craft beer, or a spooky ghost hunt immersive experience.
Quick Overview
Our list includes a variety of drinking tours designed to show off Orlando’s local flavor and scenery. You’ll find a pontoon pub crawl that takes you across five lakeside bars (), a scenic paddle adventure with craft beer tastings (), and a haunted pub crawl exploring Orlando’s spooky side (). Other options include a craft beer and historic tour of Sanford, a virtual bar crawl for a flexible experience, and even a ladies’ pontoon tour with lunch, perfect for a more relaxed day. Each one offers something different, from scenic watercraft to walking explorations and ghost stories.
1. Pontoon Pub Crawl, 5 Lakeside Pubs and Restaurants Visit by Boat
If floating through Winter Haven’s Chain of Lakes sounds appealing, this pontoon pub crawl is a one-of-a-kind way to enjoy Orlando’s nearby waterways. For about $90, you’ll spend around three hours with a small group and a knowledgeable guide, starting at Tanners Lakeside Restaurant & Bar. The trip takes you on a relaxing ride across five lakes, stopping at popular lakeside pubs and restaurants, each offering drinks and snacks (own expense).
What makes this tour stand out is the combination of scenic water views, wildlife sightings—including possible alligators—and the chance to socialize in a laid-back setting. Captain Dave is known for his engaging stories and personalized approach, making this trip both fun and informative. Guests consistently praise the guide’s local knowledge and the relaxed atmosphere, often mentioning how the sunset views add a memorable touch.
This tour is especially suited for groups seeking a stress-free, scenic party on the water. The small-group setting guarantees personalized attention and flexibility, perfect if you want to avoid the large bus crowds typical of some pub crawls. A minor consideration is that you’ll need to budget for drinks and bites at each stop, as they are not included.
Bottom Line: For a relaxed, scenic, and social experience on Orlando-area lakes, this boat pub crawl offers good value and lasting memories.
2. Paddle and Brew Adventure in Tavares with Beer Flight Tasting
This tour combines paddling on Lake County’s scenic waterways with a craft beer tasting at BRÜ Tap House. For $90, you’ll spend about three hours exploring the Dora Canal, known for its wildlife and natural beauty. Led by Katrina, a knowledgeable guide, you’ll paddle through protected wetlands, spotting alligators, turtles, and a variety of bird species in their natural habitat. The trip is designed to be easy enough for most skill levels, making it accessible for families or casual paddlers.
After the paddle, you’ll visit BRÜ Tap House, where you can enjoy a flight of 30 different craft brews and learn about each beer’s story. The combination of nature and local brews makes this a well-rounded experience that appeals to outdoor lovers and beer enthusiasts alike. The reviews highlight Katrina’s warmth and her expertise on local wildlife and ecosystems. One guest noted, “It was so beautiful to explore natural Florida, and the beer tasting was the perfect way to cap off the day.”
This tour is ideal for those wanting a half-day adventure that blends scenery with craft beer sampling. It’s particularly suited for nature lovers who enjoy a relaxed paddle and a social drink afterward. Keep in mind, the tour ends at the brewery, so plan your transport accordingly.
Bottom Line: A smooth mix of outdoor exploration and craft beer tasting, perfect for anyone looking to combine physical activity with flavorful drinks.
3. Orlando Haunts Boos and Booze Haunted Pub Crawl
For those intrigued by ghost stories and haunted history, this haunted pub crawl offers a spooky twist on Orlando’s nightlife. Priced at $30 and lasting around two hours, the tour takes you through the Central Business District, with stops at bars where you can sip on local brews and cocktails. Your guide shares eerie tales about Orlando’s haunted spots, including stories of UFO sightings and ghostly apparitions.
The highlight is the chance to explore Orlando’s darker side. You’ll hear about the courthouse where Ted Bundy was tried, and visit the Kress Building, famous for its UFO encounters. The tour also takes you inside historic venues like the Grand Bohemian, where you might catch the “song of an arsenic-poisoned lounge singer.”
This tour is best suited for those interested in history with a spooky flair. It’s a quick, affordable way to learn about Orlando’s haunted culture while enjoying drinks in atmospheric locations. The reviews are mixed, but many appreciate the storytelling and immersive atmosphere, making it a fun, if slightly spooky, night out.
Bottom Line: A short, atmospheric adventure for anyone who enjoys ghost stories and a bit of the supernatural with their drinks.
4. Sanford’s Craft Beer and History Tour
Just north of Orlando, Sanford offers a charming small-town vibe paired with a thriving craft beer scene. This craft beer and history tour costs around $34 and lasts approximately 1 hour and 45 minutes. Led by a BJCP Certified Beer Judge, you’ll walk through Sanford’s historic streets, learning about its prohibition-era past while stopping into three local breweries.
The tour begins at the Sanford Homebrew Shop, a hub for local brewers, before visiting Sanford Brewing Company and Wops’ Hops Brewing. Each brewery offers a different style of beer, from classic ales to innovative local brews. Guests rave about the host’s knowledge and the opportunity to ask questions about brewing techniques and local history.
What makes this tour worthwhile is the combination of small-group intimacy, educational insight, and authentic local flavors. It’s best suited for beer enthusiasts interested in regional history and craft brewing. The main limitation is the shorter duration, so it’s ideal if you’re tight on time but still want a taste of Sanford’s beer scene.
Bottom Line: A compact, informative tour packed with beer and local stories, perfect for those who want to learn and sample in one go.
5. Orlando Virtual Bar Crawl & Scavenger Hunt
This digital experience offers a self-guided virtual bar crawl and scavenger hunt for just over $12. It’s designed for smaller groups or families who want flexible fun without leaving home or hotel rooms. You’ll be directed to four bars that are sometimes tricky to find alone, with challenges involving photos, videos, and trivia to spice up the adventure.
While it doesn’t include physical drinks, it encourages learning about Orlando’s bars and landmarks in a playful, competitive way. It’s suitable for families, small groups, or travelers on a budget who enjoy interactive games and want to discover Orlando’s local flavor virtually.
The reviews are limited, but the concept appeals to those wanting a cost-effective and adaptable way to explore Orlando’s drinking scene. Keep in mind, this is a virtual experience, so it’s different from the physical tours described above.
Bottom Line: A flexible, fun, and inexpensive way to explore Orlando’s bar scene from anywhere, ideal for tech-savvy travelers.
6. Ladies Luncheon Pontoon Tour (Gentleman welcome)
This ladies’ pontoon tour offers a relaxed four-hour cruise through Orlando’s Chain of Lakes, with a focus on scenery, wildlife, and casual dining. For $100, you’ll enjoy lakeside views, wildlife sightings—like otters and herons—and a variety of restaurants along the way. You might see a waterski show at Legoland Florida if timing allows, adding a lively spectacle to the trip.
The itinerary includes a stop at Historic Cypress Gardens and visits to restaurants such as Tanners Lakeside and Caribbean Bay. The tour is designed to be gentle and scenic, with plenty of opportunities for photos and wildlife watching, making it well-suited to a laid-back day with friends or family. The longer duration allows for more socializing and sightseeing.
While this tour doesn’t include drinks in the price, it offers a beautiful natural setting with optional food and beverages available at each stop. It’s excellent for those who want a casual, scenic cruise with a touch of local history and wildlife.
Bottom Line: Perfect for a relaxed, scenic outing on the lakes with light dining options and wildlife viewing.
7. Happy Hour Downtown Pub Crawl
For a walking tasting tour, this happy hour pub crawl in Winter Haven focuses on sampling various cuisines and drinks across downtown. Starting at $139, it’s a more immersive, social experience lasting about three hours. The tour visits several establishments—from pizza and burgers to sushi and cocktails—giving you a broad taste of local flavors.
During the walk, you’ll learn about Winter Haven’s local businesses and architecture, making it more than just a pub crawl. The stops include Tsunami Sushi, Union Taproom, Adler’s Burgers, and more, each offering a different culinary experience. This tour is especially suited for foodies and those wanting a personalized experience.
Guests often appreciate the variety and the opportunity to interact with local owners and staff. The tour’s length and variety make it a good option for a full evening of socializing. Be prepared for a walking pace and to pace yourself across multiple stops.
Bottom Line: A lively, diverse way to explore Winter Haven’s drinks and eats, ideal for small groups seeking a full evening of tasting.
8. Ghost Tour and Pub Crawl
Combine history, ghost stories, and drinks on this 3-hour ghost tour through Orlando’s Winter Haven. For $139, your guide shares tales of hauntings, spirits, and local legends as you visit several downtown venues. The tour includes stops at the Ritz Theater, Grove mural walk, and Barrel 239, where spooky stories and drinks create a fun, eerie atmosphere.
This tour is perfect for those interested in the supernatural but who also want to enjoy some casual drinks with a group. The storytelling is lively, and the mix of history and supernatural lore makes it more than just a bar crawl. The route takes you through historic buildings and some lesser-known local legends, adding depth to the experience.
While it doesn’t focus solely on drinking, many stops include the chance to enjoy beverages while listening to ghostly tales. It’s a good fit for adventurous travelers who enjoy a dose of spooky fun along with drinks.
Bottom Line: For thrill-seekers and history buffs alike, this ghost and pub crawl offers a memorable way to explore Orlando’s haunted side.
How to Choose the Right Drinking Tour in Orlando
Picking the best tour depends on your interests, budget, and how active you want to be. If you enjoy a scenic, relaxed experience on water, the [Pontoon Pub Crawl]() offers a unique lakeside party. For those wanting nature and craft beer, the [Paddle and Brew Adventure]() combines outdoor fun with tastings. If thrill or spooky stories excite you, the [Haunted Pub Crawl]() and [Ghost Tour]() are great options.
The craft beer tour of Sanford provides a more educational focus with local breweries, perfect for beer fans with a bit of history. The [Virtual Bar Crawl]() offers flexibility for travelers who prefer to explore from home or a hotel. Budget-conscious travelers may prefer the lower-cost [virtual experience](), while those wanting a more personalized, social outing might choose the happy hour pub crawl.
Think about how much activity you want — whether it’s paddling, walking, or just relaxing on a boat — and whether you prefer daytime wildlife views or evening ghost stories. Booking early is recommended, especially for tours with limited availability or seasonal peaks.
To sum it up, Orlando offers a surprising variety of drinking tours that cater to different interests. For a lively lakeside party, the Pontoon Pub Crawl is unbeatable. If you prefer scenic outdoor adventures with craft beers, the Paddle and Brew Adventure delivers. For those enchanted by spooky stories and haunted history, the Ghost Tour and Haunted Pub Crawl provides an engaging experience. Travelers interested in local beer culture should consider the Sanford craft beer tour, especially if they want a mix of history and tasting.
Whether you’re seeking a relaxed cruise, an active paddle, or an eerie night, Orlando’s drinking tours are worth exploring. Be sure to book ahead to secure your spot, and enjoy discovering a different side of central Florida’s vibrant scene.