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

A pontoon pub crawl makes a fine change from Orlando’s theme parks: you travel between five waterside pubs by boat, through the canals and lakes of Winter Haven’s Chain of Lakes. The ride is part of the outing, not just transport between drinks, and you may spot wildlife along the way.

I like two things in particular: the small group, capped at eight, gives the captain room to adapt the outing, and the route pairs lake views with local food and pub stops. Captains Dave and Scott have also shared area history along the way, giving the ride more substance than a simple bar shuttle.

One consideration: the $90 price covers the boat tour, not your food or drinks. And Florida weather matters here. A chilly, windy evening can make an open-air cruise less comfortable, so check the forecast and dress for the water.

What makes this Winter Haven boat crawl different

• Five stops by boat: Visit five pubs or restaurants on the lakeshore, with the route linking them through the Chain of Lakes.
• A small group: The boat is limited to eight people, so it can feel more like a shared outing than a big organized cruise.
• Local stories on the ride: Captain Dave is often at the helm, and Captain Scott has also guided trips. Captains share area history as you travel.
• Wildlife along the way: Keep an eye out for birds and other lake life. An alligator is possible, not guaranteed.
• Food and drinks are extra: Buy them at the stops, or bring your own items aboard. A cooler and ice are available upon request.
• Three hours on the water: The tour starts and ends at Tanners Lakeside Restaurant & Bar in Winter Haven.

Start at Tanners Lakeside Restaurant & Bar

The meeting point is Tanners Lakeside Restaurant & Bar, at 1006 Lake Howard Drive SW in Winter Haven. The tour returns here after roughly three hours, which makes planning the rest of your evening straightforward.

The location is in Winter Haven, not central Orlando. If you are staying near the theme parks, allow time to get to the meeting point and back. That drive can feel like part of the appeal: this outing takes you away from Orlando’s busy visitor corridor and into a lake town where the water is part of everyday life.

The experience is offered in English, and your ticket is mobile. It is a small-group activity with a maximum of eight people. That cap matters: you have more chance to ask questions, chat with the captain, or say what sort of stops you are in the mood for.

Cruise the Chain of Lakes between pub stops

Once aboard, the captain navigates while you settle in and enjoy the ride. The route travels through the Winter Haven Chain of Lakes, using both open water and connecting canals. That changing scenery is a key part of the outing, especially around sunset, when the light can make the water feel like a destination in its own right.

There is no need to steer or plan the route. Captains take care of navigation, and the boat ride gives you a chance to relax between the social parts of the evening. Local history is often folded into the trip, so you can learn a little about the area while moving from one shore-side stop to the next.

Wildlife is another bonus, though it is best treated as a possibility rather than a promise. Alligators have been spotted near the boat, including at night, but sightings depend on conditions and luck. Keep a respectful distance and follow the captain’s direction if an animal appears.

Five pubs, five chances to find a local favorite

The tour visits five of the operator’s favorite pubs and restaurants along the lakes. The exact venues are not named in advance, so go expecting a selection of places with distinct atmospheres rather than a fixed list of famous bars. Some stops may suit a quick drink; at others, you may want to linger over food.

The variety is part of the fun. The stops have included casual local spots where you can order a drink, share a few plates, and get a feel for the people who live around the lakes. Food mentioned on past outings includes gator bites, oysters on the half shell, crab cakes, and boiled peanuts. Menus change, so don’t count on any one dish being available.

The captain can offer suggestions at each stop, and the overall pace may be adjusted to the group’s preferences. That flexibility is useful if you want a more relaxed evening or are celebrating with friends. Still, five stops in about three hours means each visit is likely to be a taste of a place rather than a long meal. If you want to make a full dinner of it, consider ordering strategically or eating before you go.

A few outings have ended with karaoke or a singalong, but that is a happy extra, not a scheduled feature. Treat it as a possibility if the mood and venue line up, not something to plan your night around.

Captain Dave, local stories, and a personal pace

Captain Dave is the guide most often named, and Captain Scott has also led trips. Dave’s role goes beyond piloting the boat: he has shared local history, suggested food and drinks, and adjusted the experience to suit the group. His easygoing approach seems especially useful for mixed groups, where some people may want more sightseeing and others are ready to get to the next pub.

The intimate size also makes it easier to meet the other people aboard. If you book with a partner or family, you may find yourselves sharing the boat with another small party. That can add to the evening’s social feel, though it also means the tour is not a private cruise unless your group fills the boat.

This is a good fit for birthdays, anniversaries, a friends’ night out, or a low-key family outing with adults who enjoy a pub stop. It is less suited to anyone who wants a quiet nature cruise without food and drink stops, or a tightly timed itinerary with named venues and set menus.

What $90 buys, and what you pay for separately

At $90 per person, you are paying for about three hours on the water, the captain’s navigation, access to five lakeside stops, and a small-group format. The value depends on what you want from the evening. If you would otherwise book a boat ride and visit several local pubs separately, combining the two can make for a distinctive outing and save you the work of planning the route.

Food and alcoholic drinks are not included. You buy them at the bars and restaurants, and you can bring your own items onto the boat if you prefer. A cooler and ice are available upon request, which is handy if you bring drinks, but ask ahead so you know what is arranged.

Keep your spending expectations realistic: the $90 is only the tour price. Your final cost will rise with anything you order at the stops. On the other hand, you are not paying for a packaged meal or a fixed drink menu you may not want.

Weather, timing, and a few useful preparations

Because the boat is open to the weather, conditions can shape the experience. One chilly, windy outing still went ahead with blankets and hot drinks, but that does not mean every trip will have the same provisions. Bring a warm layer for evening departures, especially when the forecast looks cool or breezy. Sunset views are appealing, but the later the hour, the more important it is to dress for the temperature.

The activity requires good weather. If poor weather cancels the tour, you can be offered another date or a full refund. You can also cancel for a full refund if you do so at least 24 hours before the start time. Changes or cancellations inside that 24-hour window are not accepted for a refund.

The stated maximum is eight people, with a group weight limit of 1,600 pounds. If that limit may apply to your party, check with the operator before booking. Service animals are allowed, and the meeting point is near public transportation, though you should confirm the best way to reach it for your own plans.

Who should book this lake-and-pub outing

Book it if you want a social evening that mixes a boat ride, local places to eat and drink, and a little regional history. It is particularly appealing if you are staying in the Orlando area and want to spend part of a day somewhere less tied to theme parks. Couples can enjoy it as an easy date, while friends and families can use it for a birthday or a relaxed group get-together.

Think twice if you need a guaranteed alligator sighting, a particular pub, or a meal included in the ticket. The route is flexible, the wildlife is unpredictable, and you cover your own food and drinks. For the right group, though, the appeal is precisely that it feels less like a packaged attraction and more like an evening out on the lakes with a local captain showing you around.

FAQ

Where does the tour start and end?

It starts and ends at Tanners Lakeside Restaurant & Bar, 1006 Lake Howard Drive SW, Winter Haven, Florida.

How long is the boat pub crawl?

The experience lasts about three hours.

How many pubs and restaurants does the tour visit?

The tour visits five pubs or restaurants on the shores of the Winter Haven Chain of Lakes.

Are food and drinks included in the $90 price?

No. Food and alcoholic drinks are not included. You can buy them at the stops or bring your own items aboard.

Can I bring my own drinks?

Yes. You may bring your own items onto the boat. A cooler and ice are available upon request.

How many people can join the tour?

The boat has a maximum of eight people per tour. The stated group weight limit is 1,600 pounds.

Are alligator sightings guaranteed?

No. Alligators may be seen in their natural environment, but sightings are not guaranteed.

What happens if bad weather cancels the tour?

If poor weather cancels the experience, you will be offered a different date or a full refund. You can also cancel at least 24 hours before the start for a full refund.