Clearwater Beach: Private Boat Day with Slide & Island Stops

Summary

Private boat trip from Clearwater Beach with dolphins, island stops and a waterslide for families or friends

You’ll cruise Clearwater Beach on a private boat with your own captain, spot wild dolphins up close, hop off at Caladesi and Honeymoon Islands for shelling or swimming, and laugh your way down a waterslide into warm Gulf waters. Expect quiet moments too—just you, sand between your toes, salty air—and stories you’ll replay long after you’re back on shore.

What’s the experience like?

We stepped barefoot onto the Avalon Funship at Clearwater Beach, sunscreen still sticky on my arms and everyone already joking about who’d be first down the slide. Our captain, Mike—local guy, quick with a story—gave us the safety rundown (I half-listened, distracted by pelicans flapping nearby), then we pulled away from the dock. The engine’s hum mixed with seagull calls and that weirdly sweet smell of sunscreen and seaweed. I kept glancing back at the shoreline getting smaller, thinking how different everything looks from out here.

Dolphins showed up before I’d even finished my coffee—seriously, right there next to us, just sliding through the water like they owned it. Mike slowed down so we could watch them; my niece squealed so loud I think she scared one off. We passed by Caladesi Island (only boats can get there), white sand almost blinding in the sun. Jumped off to go shelling—felt like kids again poking around for perfect ones. The sand was warm but not hot enough to burn your feet yet. There was this moment where everyone just kind of fell quiet, listening to waves and wind rustling through those scraggly pines.

Honeymoon Island came next—long stretch of beach and more birds than people. My cousin tried to name them all (she’s into birdwatching now?), but honestly I just remember the osprey circling overhead and how salty my lips tasted after swimming. We anchored near Three Rooker Bar too; never heard of it before but apparently it wasn’t even here a decade ago. The water’s shallow enough that you can stand waist-deep and talk without shouting over waves—which is exactly what we did, passing around bottled water from the cooler and daring each other to take another turn down the slide.

I didn’t expect to feel so relaxed—or maybe loose is a better word? Like time didn’t matter much out there. Mike told us little things about each spot: how Caladesi stays wild because you can only reach it by boat, or how Honeymoon’s got these old pine forests if you wander inland a bit. It was easygoing in that way Florida sometimes is when you’re not fighting crowds or traffic lights or schedules.

Step-by-step itinerary

Day 1 — Private boat tour and island visits

• Safety briefing on boat
• Cast off from Clearwater Beach
• Cruise north to barrier islands
• Spot dolphins and local wildlife
• Visit Caladesi Island for shelling
• Explore Honeymoon Island beach and trail
• Visit Three Rooker Sand Bar island
• Swim and snorkel in Gulf waters
• Enjoy complimentary water and floats

Top questions

How many people can join the private boat tour?

The private boat charter accommodates up to 10 passengers per booking.

Is pickup included for this Clearwater Beach boat day?

The tour includes pickup and drop-off at a designated meeting point near Clearwater Beach.

What islands do we visit during the tour?

You’ll visit barrier islands such as Caladesi Island State Park, Honeymoon Island, and Three Rooker Bar.

Are dolphins guaranteed on this private boat tour?

Dolphin sightings are very likely but not guaranteed as they are wild animals in their natural habitat.

Can we swim or snorkel during the trip?

Yes, guests often swim and snorkel at various stops including secluded beaches and sandbars along the route.

Is lunch provided on board?

No lunch is provided but complimentary bottled water is included; you may bring your own snacks or food.

What should I bring for shelling on Caladesi Island?

The tour provides mesh shell bags for collecting shells while exploring Caladesi Island’s beaches.

Are life jackets available for all ages?

Yes, life jackets and safety equipment are provided for all guests regardless of age.

What’s included

Your day includes pickup and drop-off at a designated meeting point near Clearwater Beach, a private double-decker Funship with waterslide and local captain as your guide, fuel costs covered, bottled water in an ice-filled cooler, Big Joe floats for lounging in the water, mesh bags for shelling adventures on Caladesi or Honeymoon Islands, plus all necessary life jackets and safety gear before returning ashore together.