1. Playin' Hooky Charters

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Tierra Verde, FL

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Playin' Hooky Charters

5.0 (4 reviews)
Open • Open 24 hours

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Island Ferry St Pete Beach - Sunset cruise

Island Ferry St Pete Beach

4.8(55 reviews)
3.9 mi

Wow! What an experience! We took a 9am tour to Shell Key on Cap'n Dalton's boat. There were only…read moresix passengers on board, which meant there was plenty of room to spread out and enjoy the sunshine. Dalton provided expert commentary about the area, even pointing out a few celebrity homes and yachts along the way. It was a gorgeous ride over to Shell Key, and we even saw a few dolphins along the way. Once on the island, we had about 45-50 minutes to explore the beaches and do a little snorkeling and shell-hunting. The island is aptly named, with rows and piles of shells along its white, sandy beaches. The water was warm and perfect for swimming. Soon enough we were back on board and heading back to the harbor. And that's when the magic happened: dolphins! Following along in our wake, and no doubt attracted to the enthusiastic squeals of one of our dolphin-loving fellow passengers, the dolphins put on quite a show. Even Dalton, who I assume sees a LOT of dolphins, was impressed by how long they followed in our wake and performed jumps and flips for us. It was truly one of the most remarkable experiences of my life! Thank you Dalton and Island Ferry for an amazing and memorable tour and one of the true highlights of our vacation!

Lovely tour! Our guide was very nice and chill, she definitely wanted to make sure we had a good…read moretime. Obviously its never a guarantee, but we saw dolphins and a manatee on our tour. Groups are small and the boats are very comfortable. They use pontoon boats so you have shade, which I definitely appreciated. The beach they took us to to snorkeling was gorgeous.

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Island Ferry St Pete Beach - Sunset

Sunset

Island Ferry St Pete Beach
Island Ferry St Pete Beach

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The Living Water Boat Cruises - Baby Gator

The Living Water Boat Cruises

4.9(47 reviews)
63.9 mi

I took the 2-Hr Sunset Cruise in July and had such a memorable time. Captain Sage gave an…read moreOUTSTANDING tour. Her knowledge, enthusiasm, and skills were everything you'd want on a boat tour, especially if you're like me visiting the area for the first time. I found the landmarks, wildlife, and local history to be fascinating, and this was also a wonderful way to beat the summer heat. It was just myself and another party of three on the tour. A relaxing time was had and I was so taken with the scenery and landscapes as they are so different from where I live. I highly recommend this tour for visitors and locals alike and would definitely take another tour of theirs if given the chance.

I'm a Florida native and have visited Winter Haven many times over the years, but I had never had…read morethe opportunity to experience the Chain of Lakes from the water. I'm so glad I finally did the Living Water Boat Cruises pontoon tour--it gave me an entirely different perspective on the area. One of the highlights for me was cruising past the former Cypress Gardens property, now part of LEGOLAND. I remember visiting Cypress Gardens as a child, so it was fascinating and nostalgic to see the property from the water, including the historic Florida-shaped swimming pool that is being restored and the beautiful old Florida vegetation. Our captain and guide, Sage, was excellent. She is also a Florida native and was extremely knowledgeable about the local history, the lakes, and the wildlife. During the tour we saw ospreys, otters, an alligator, and many different birds. We even got to watch floatplanes landing and taking off on the lakes, which was an unexpected treat. We toured the southern portion of the Chain of Lakes early in the morning, which was perfect because it was an extremely hot Florida day with temperatures expected in the 90s. The timing made the trip very comfortable and enjoyable. I especially appreciated that I happened to be the only guest on my tour and they still accommodated me rather than canceling. It ended up feeling like a wonderful private tour. This was such an enjoyable way to experience a part of Florida that I had never really seen before, despite growing up here. I would highly recommend it to visitors as well as longtime Floridians who want to see Winter Haven and the Chain of Lakes from a completely different perspective

Photos
The Living Water Boat Cruises - Group picture, taken by the captain

Group picture, taken by the captain

The Living Water Boat Cruises - Going through the canal under the railroad tracks to get to the lakes

Going through the canal under the railroad tracks to get to the lakes

The Living Water Boat Cruises

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Topwater Kayak Outpost

Topwater Kayak Outpost

4.8(35 reviews)
8.7 mi

Topwater Kayaks is top notch! It is conveniently located conveniently inside Fort DeSoto with…read moredirect water access (no hauling kayaks to a launch spot, no dredging through a crowded/murky marina). We rented 2 paddle boards and 3 single kayaks this morning and headed out for a very lovely morning on the water! This was our first trip out of this area, and it appears to be quite popular with kayakers and paddle boarders. The scenery is all nature and all beautiful, shallow water that was a little on the murky side today until we got out of the mangroves and into more open water where the bottom was visible. The launch area is secluded and surrounded by mangroves, and the sights are beautiful from the minute you launch. On our way out, we saw a bright red water snake and some crabs along the shore. Along our kayaking route, we spotted lots of small fish, friendly cormorants, manatees, and (possibly) a large tarpon. We saw a quite a few manatee snouts poking up from the water along our route, which was very cool...to see them, you kind of have to sit quietly and still for a bit and skim the water. Something very large got spooked under my son's kayak causing a huge stir in the shallow water, which scared him half to death and for a moment we thought he'd actually tipped over. The guys at the rental counter said it was most likely a large tarpon. They (the staff) were GREAT...super helpful and super friendly. They provide all the equipment you need, single or double kayaks, paddle boards, oars, life jackets, bottled water available. Don't forget to bring a water resistant Bluetooth speaker, towels, and some sunblock. We will definitely be returning to Topwater soon!

Went there today - was told not one bike was working. And we had to make reservations online. It…read moreclearly states on their websites reservations are not allowed. What a waste and a joke of a company.

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Topwater Kayak Outpost
Topwater Kayak Outpost
Topwater Kayak Outpost - Fishing

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Fishing

Party On Yacht Charters - Sunset

Party On Yacht Charters

5.0(1 review)
1.6 mi•South St. Petersburg - Edit

John & Amber were a fantastic crew for the day trip we went on. They are so hospitable and safety…read moreis #1 priority for them which I appreciate. Perfect for family trips or a good time with friends. We will definitely book again!

From the owner: Party On Yacht Charters is a Veteran-owned business in St. Petersburg, Florida, and your go-to…read moreluxury charter for cruising in style in the beautiful blue waters of the Gulf of Mexico to many of the area’s magnificent islands, soft-sanded sandbars, dockside restaurants and tiki bars, or simply sun-soaking while on the water exploring. Choose your own adventure to include dolphin and manatee sightings, private themed parties, sunsets, and much much more… We’d love to have you join us on our select party options to let the good times roll as we welcome you and your crew aboard with complimentary captain hats and party beads for everyone. Your private yacht comes with an USCG licensed Master Captain and a fun crew that’s sure to bring smiles, laughs, and many memorable moments that will make you want to come back to join us again and again. Take a break from it all, climb aboard with your friends and family, and enjoy the fresh ocean air, alluring sights, and the sweet sounds of your favorite tunes on the Bluetooth sound system. So what are you waiting for? Book your fun adventure on the water today for up to six people.

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Party On Yacht Charters - Dolphins

Dolphins

Party On Yacht Charters - Party on yacht charters

Party on yacht charters

Party On Yacht Charters - Shell Key

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Shell Key

Playin' Hooky Charters - boating - Updated November 2026

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