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

A lively boat pub crawl in Winter Haven offers a unique way to explore the Chain of Lakes region. For $90 per person, this 3-hour tour takes small groups aboard a pontoon boat to visit 5 popular lakeside pubs and restaurants. The tour departs from Tanners Lakeside Restaurant & Bar and guarantees a personalized experience with a maximum of 8 travelers. The small group size ensures relaxed pacing and meaningful interactions with the friendly guide, who shares stories about the area’s wildlife and history.

The journey combines scenic water views, wildlife sightings — including the chance to see alligators — and stops at some of the most quirky and charming bars along the lakeshore. Travelers can order drinks and food at each stop, though these are at their own expense. This tour is ideal for groups seeking fun, relaxation, and a local flavor, with many booking 23 days in advance owing to its popularity.

Key Points

• Small-group experience with a maximum of 8 travelers guarantees personalized attention
• 3-hour tour visiting 5 lakeside pubs and restaurants in Winter Haven’s Chain of Lakes
• Guided by Captain Dave, who shares local history, wildlife info, and recommendations at each stop
• Includes a scenic boat ride through Winter Haven’s lakes, with wildlife sightings like alligators
• Flexible and stress-free, with food and drinks available for purchase at each location
• Highly rated (5.0/5 from 92 reviews), praised for fun, friendliness, and knowledgeable guides

Starting Point and Tour Duration

The pontoon pub crawl begins at Tanners Lakeside Restaurant & Bar, located at 1006 Lake Howard Dr SW in Winter Haven. The tour lasts approximately 3 hours, providing enough time to visit five lakeside venues without feeling rushed. The short duration makes it easy to fit into an afternoon or early evening plan, and the mobile ticket simplifies check-in.

Since most travelers book about 23 days ahead, securing a spot early is recommended. The tour ends back at the starting point, making logistics straightforward whether you’re staying nearby or heading back to Orlando.

Exploring the Chain of Lakes

The main stop is in Winter Haven, where the boat ride showcases the region’s natural beauty. As the pontoon glides across the lakes, you’ll spot wildlife such as birds and possibly an alligator in its natural environment. The scenic waterway offers a refreshing change from typical land-based pub crawls, combining relaxation with entertainment.

The guide leads the group through the lakes, sharing stories about local wildlife and the area’s history, which many reviews highlight as a key feature that elevates the experience beyond just drinking.

The Lakeside Pubs and Restaurants

The five stops are carefully selected for their unique character and local charm. Each venue offers drinks and bites—which are paid for individually—allowing guests to sample gator bites, oysters, crab cakes, or boiled peanuts at different locations. These stops provide a variety of atmospheres — from cozy taverns to lively restaurant-bars.

While the stops are eclectic, reviews note that the pubs are friendly and well-chosen, offering a mix of casual, quirky, and welcoming environments. This variety adds to the fun and relaxed feel of the trip.

Captain Dave’s Role and Personal Touch

Captain Dave is a standout feature of this tour. Reviews consistently praise his knowledgeable and personable approach, describing him as engaging, accommodating, and funny. He not only guides the boat smoothly but also shares local stories, history, and recommendations at each pub.

Guests appreciate how Captain Dave creates a personalized experience, making everyone feel comfortable. His sense of humor and ability to keep the mood lively, especially with karaoke moments, contribute to the overall enjoyment.

Scenic Waterway and Wildlife Sightings

One of the tour’s most appreciated aspects is the scenic boat ride itself. The gliding across Winter Haven’s lakes offers stunning views, especially during sunset hours, which many reviews highlight as a highlight.

The chance to see local wildlife, especially alligators and birds, adds an unexpected element of nature-watching that appeals to those looking for more than just a pub crawl. This combination of water scenery and wildlife makes the trip feel like a mini adventure.

Flexibility and Group Atmosphere

The tour is designed for relaxation and fun, with a small group size that fosters personalized interaction. The maximum of 8 travelers ensures that everyone can enjoy the experience without feeling crowded.

The flexible nature of the tour allows guests to order drinks and food at their own pace, making it suitable for both lively groups and more laid-back couples. Many reviews mention the friendly atmosphere and the opportunity to meet new people.

Weather and Timing Considerations

Since the tour depends on good weather, it’s recommended to check the forecast before booking. Cancellations due to poor weather are fully refunded or rescheduled, providing peace of mind.

The timing of the tour allows for sunset views, which many guests find particularly memorable. If booking for later in the day, prepare for a chilly evening in cooler months, and consider an earlier start for warmer conditions.

Booking and Cancellation Policy

This tour offers free cancellation up to 24 hours before the scheduled start, giving flexibility in case of last-minute changes. All bookings are made via a mobile ticket, ensuring quick and easy access.

The price of $90 per person covers the 3-hour experience, with the option to customize your day with stops at charming lakeside venues. The small group size emphasizes a personalized, intimate experience.

Why Choose This Tour in Winter Haven

This pontoon pub crawl distinguishes itself with its scenic waterway, wildlife sightings, and friendly guide. It’s a perfect choice for those wanting a relaxed, engaging day on the water, combined with good local pubs and great company.

The positive reviews reflect a consistent level of fun, professionalism, and personalized attention. While the cost may seem higher than land-based pub crawls, many find the scenic setting and relaxed vibe worth the price.

Who Will Love This Experience?

This tour is especially well-suited to small groups of friends, couples, or celebrating a special occasion like birthdays or anniversaries. It’s also ideal for anyone interested in wildlife and scenic views alongside their drinks.

Those who appreciate knowledgeable guides and a laid-back atmosphere will find this boat pub crawl both enjoyable and memorable. However, travelers should be prepared for individual costs for food and drinks at each stop.

Frequently Asked Questions

Is there a minimum or maximum group size?
Yes, the tour is limited to 8 travelers, ensuring a small, intimate experience.

What should I bring?
Guests should bring cash or cards for drinks and bites, and dress comfortably for the weather conditions, especially if booking during cooler months.

Can service animals participate?
Yes, service animals are allowed on the tour.

What if the weather is bad?
The tour will be canceled or rescheduled due to poor weather, with a full refund or alternative date offered.

How early should I book?
Most bookings are made about 23 days in advance, so early reservation is recommended to secure a spot.

Is there an age limit?
While specific age restrictions aren’t listed, the focus on drinks and pub stops suggests this tour is best suited for adults.

Are food options available during the tour?
Food and drinks are purchased separately at each stop, with a variety of local bites available.

How long do stops last?
Each stop typically allows enough time to order drinks and food, with the overall experience lasting 3 hours.

This pontoon pub crawl in Winter Haven offers a relaxed, scenic, and fun way to enjoy the lakes and local bars. With friendly guides, wildlife sightings, and charming venues, it remains a highly rated choice for those seeking a different kind of pub crawl on the water.