Clearwater Beach: Private Boat Tour with Slide & Island Stops

Summary

Slide off the deck, chase dolphins, find shells on wild islands

You’ll cruise from Clearwater Beach on a private boat tour with a local captain—spotting dolphins, sliding straight into the Gulf, and hopping onto wild islands like Caladesi and Honeymoon for shelling or swimming. Feel salt in your hair, sand between your toes, and maybe find yourself laughing at something unexpected along the way.

What’s the experience like?

I’ll never forget how quiet it got when we first left Clearwater Beach behind—just the low hum of the engine and that salty, sunscreeny air. Our captain, Mike, handed out cold bottled water and cracked a joke about his “office view.” He pointed out a pod of dolphins before I even finished my first sip. I didn’t expect to see them so close; their backs glistened right next to us. The kids shrieked (I might’ve too). It’s weird how quickly you forget about your phone when you’re watching wild dolphins like that.

The boat itself—this double-decker thing with a slide—was more fun than I’d guessed. My nephew dared me to go down first. I did, and yeah, the Gulf was cooler than I thought but not shocking. We anchored near Caladesi Island where the sand felt almost powdery underfoot, and there were these tiny spiral shells everywhere. My sister kept finding better ones than me; she says it’s luck but I’m suspicious. Mike told us stories about how some of these islands just show up or disappear over time—Three Rooker Bar wasn’t even here when he started guiding tours.

We drifted toward Honeymoon Island after that, passing ospreys perched on the channel markers. There was this moment—sun glinting off the water, everyone quiet for once except for someone’s laugh carrying from upstairs—that sticks with me. On the way back, I noticed my skin was sticky with salt and maybe a little sunburnt (should’ve reapplied), but honestly? Didn’t care much. Sometimes you just need an afternoon like this where nothing feels rushed or staged.

Step-by-step itinerary

Day 1 — Private boat tour and island visits

• Safety briefing on boat
• Cast off from Clearwater Beach
• Watch for dolphins and wildlife
• Visit Caladesi Island
• Explore Honeymoon Island
• Visit Three Rooker Sand Bar
• Swim, snorkel, or shell on islands
• Enjoy complimentary water and floats

Top questions

How long is the private boat tour from Clearwater Beach?

The half-day private boat tour typically lasts around 4 hours.

Is dolphin watching guaranteed on this Clearwater Beach boat trip?

Dolphin sightings are very likely but not guaranteed as they are wild animals.

What islands do we visit during the tour?

You may visit Caladesi Island, Honeymoon Island, and Three Rooker Bar depending on conditions.

Does this private boat tour include swimming stops?

Yes, you can swim in the Gulf of Mexico during island stops.

Is lunch included on this Clearwater Beach private boat charter?

No lunch is included but bottled water is provided; you can bring your own snacks.

How many people can join this private Clearwater Beach boat tour?

The maximum group size is 10 passengers per booking.

Are life jackets provided during the boat trip?

Yes, life jackets and all safety equipment are included for all guests.

Where does pickup happen for this Clearwater Beach boating experience?

Pickup and drop-off are at a designated meeting point near Clearwater Beach.

What’s included

Your day includes pickup and drop-off at a set meeting spot near Clearwater Beach, all fuel costs covered by your captain-guide (who knows these waters inside out), bottled water chilled in an ice-filled cooler, use of floats for swimming stops, mesh bags for shell collecting on Caladesi or Honeymoon Islands—and all safety gear taken care of so you can just relax into it all.