Pontoon Pub Crawl, 5 Lakeside Pubs and Restaurants Visit by Boat

A pontoon pub crawl in Winter Haven offers a refreshing twist on the typical bar-hopping experience. For around $90 per person, you’ll spend approximately three hours cruising through the scenic Chain of Lakes region, visiting five popular lakeside pubs and restaurants. Led by a friendly guide—often Captain Dave—this small-group adventure guarantees a relaxed pace, personalized attention, and plenty of opportunities to sip, snack, and soak up the stunning waterside scenery.

What we love most about this experience is how it combines nature, casual fun, and local flavor all in one outing. The views of the lakes, wildlife sightings—including the possibility of spotting an alligator—add a unique touch of wilderness. Plus, the lively atmosphere and engaging guides make each stop feel welcoming and authentic. One more highlight is the sunset views that flood the lakes, turning this into more than just a pub crawl—it’s a celebration on the water.

A possible consideration is the group size limit of eight, which keeps things intimate but might be a squeeze if you’re hoping for a large group vibe. Also, while drinks and bites are at your own expense, the stops are well-chosen for their charm and character. This tour is best suited for those who enjoy scenic outdoor activities combined with socializing, have a sense of adventure, and appreciate a laid-back, local experience that’s a bit different from the usual bar crawl.

Key Points

• Unique Water-Based Experience: Drink and socialize aboard a pontoon in beautiful lakeside settings.
• Small Group Intimacy: Max of eight travelers ensures personalized attention and flexibility.
• Expert Guides: Knowledgeable captains like Dave enrich the trip with local insights and humor.
• Scenic & Wildlife Viewing: Opportunities to see native wildlife, including the possibility of spotting an alligator.
• Great Value: Price includes a 3-hour trip with visits to five distinct pubs—good bang for your buck.
• Authentic Local Vibe: The stops are eclectic and friendly, offering a taste of Winter Haven’s casual charm.

A Detailed Look at the Pontoon Pub Crawl Experience

Imagine cruising across Winter Haven’s lakes in the late afternoon, the water shimmering under a perfect sunset sky. Your guide, often Captain Dave, welcomes you at the first stop—Tanners Lakeside Restaurant & Bar—where you start with your first drink and a quick overview of the plan. From there, the boat gently glides to four other lakeside venues, each with its own special character.

The itinerary is straightforward but packed with variety. The initial ride itself is a treat— a lively, scenic journey through the Winter Haven Chain of Lakes. As you cruise, your guide shares stories about the area—and if you’re lucky, you’ll see alligators, herons, or even some playful dolphins. This isn’t just about drinks; it’s about enjoying nature and community in a setting that’s both relaxed and lively.

Stop 1: Winter Haven

Here, the tour kicks off with some local flavor and a friendly introduction to the lakes. It’s a chance to settle in, have a drink, and get a feel for the area. The reviews rave about Captain Dave’s knowledgeable and engaging style—”Very accommodating,” “Made the trip interesting,” and “Ran a great show” are common praises.

What makes this stop special is the combination of lakeside views and the wildlife. Many travelers highlight the chance to see native animals, and some reviews even mention a visit from a curious gator. The atmosphere is casual, and the group size keeps it intimate, so everyone can enjoy the scenery and the company.

Stops 2-5: Lakeside Pubs & Restaurants

Each subsequent stop offers something unique, from quirky local favorites to more upscale dining spots. While the specific venues are not named in the provided info, reviews suggest they are fun, eclectic, and full of character.

What travelers love is Captain Dave’s personalized recommendations for food and drinks at each place—”They did not disappoint,” and “The pub stops were well chosen.” The variety of venues is part of what makes this tour memorable, offering a taste of local cuisine, such as gator bites, oysters, or crab cakes, along with craft beers or cocktails.

The Scenic Finale: Sunset & Socializing

The trip’s highlight is often the sunset views over the lakes. Several reviews mention how beautiful the scenery is, especially as the sky turns orange and pink. The relaxed pace allows everyone to snap photos and soak in the serenity before heading back to the starting point.

The Experience, From Start to Finish

The entire trip lasts about three hours, which is enough time to enjoy five stops without feeling rushed. The small group size (up to 8 travelers) ensures that everyone gets a chance to chat with the guide and each other, fostering a warm, convivial vibe. The guides receive high praise for their knowledge, friendliness, and ability to make everyone feel at home—”Captain Dave is the best,” one reviewer notes.

While drinks and bites are at your own expense, the value here is in the scenic setting, personalized service, and fun stops. The tour runs most days, with bookings made about 23 days in advance, indicating good demand among travelers seeking a unique, memorable outing.

Why This Tour Works Well

This pontoon pub crawl is perfect for travelers looking to combine outdoor adventure with social fun. If you enjoy a bit of wildlife spotting, beautiful water views, and friendly local pubs, you’ll find this trip a delightful change from traditional bar-hopping. It’s also great for groups of friends, couples, or even couples on a quirky date—the relaxed vibe suits many occasions.

Many reviews mention how the guide’s knowledge enhances the experience—adding context and stories that make the stops more meaningful. The scenic waterway and the sunset views alone make this a worthwhile outing, but the lively, welcoming stops add an extra layer of charm.

How to Make the Most of It

Dress comfortably, especially if you’re planning to spend time outdoors and on the water. Bring a hat and sunscreen for daytime trips, and if you’re doing an evening float, a light jacket might help as it can get breezy. Remember, drinks and snacks are paid for separately, so plan your budget accordingly.

Book ahead—this experience is popular, averaging 23 days in advance—and plan for a relaxed, fun-filled three hours. Arrive at the meeting point, Tanners Lakeside Restaurant, ready for a friendly, scenic adventure that’s all about good company and great views.

The Sum Up

This Pontoon Pub Crawl in Winter Haven offers a delightful mix of scenery, local charm, and casual fun. It’s ideal for those who want a more authentic, laid-back way to explore the Lakeside region while enjoying some drinks and good company on the water. The small-group setting guarantees personalized attention from a knowledgeable guide, making each trip feel special.

If you’re seeking a break from crowded, busy bars and want to combine your love of nature with socializing, this tour ticks all the boxes. The views alone are worth it, but the friendly atmosphere and well-chosen stops make it a true standout for anyone looking to experience Winter Haven in a relaxed, memorable way.

For travelers who value authentic local experiences, enjoy scenic waterside settings, and appreciate attentive guides, this pontoon pub crawl will leave you with stories—and perhaps a little gator sighting—that you’ll talk about for a long time.

FAQ

Is this tour suitable for all ages?
The tour is most suitable for adults, as drinks are at your own expense. It’s designed for those comfortable on a boat and in outdoor settings.

How many people are in each group?
The tour is limited to a maximum of 8 travelers, ensuring a small, intimate experience with lots of personal attention.

What is the duration of the tour?
The entire experience lasts about 3 hours, including visits to five lakeside pubs and the scenic cruise.

Are drinks included?
No, drinks and bites are paid for separately at each stop. The tour provides the transportation and guide service.

What should I wear?
Dress comfortably for the weather; bring sun protection, and a light jacket if needed for evening cruises. Shoes should be suitable for being on a boat.

What happens in case of bad weather?
The tour requires good weather. If canceled due to poor conditions, you’ll be offered a different date or a full refund.

This unique lakeside adventure combines the best elements of outdoor exploration, local hospitality, and scenic beauty—making it a memorable way to see Winter Haven from a whole new perspective.