Clearwater Beach: Private Boat Tour with Slide & Island Stops

Summary

Barrier island hopping dolphins and laughter on a double-decker boat

You’ll cruise Clearwater Beach’s turquoise waterways on a private double-decker boat with slide, spotting wild dolphins and anchoring at quiet islands for swimming or shelling. Your local captain handles everything—just bring your people and let the Gulf air work its magic. Expect laughter, salty hair, and moments you’ll replay long after you’re home.

What’s the experience like?

I’ll admit, I almost lost my hat when we hit the first patch of wind leaving Clearwater Beach — but honestly, that’s when it started to feel real. Our captain (Mike? Mark? I’m terrible with names) grinned and told us to keep our eyes peeled for dolphins. Not five minutes later, someone yelled and there they were, just gliding alongside the boat like it was their morning commute. The water had that weirdly clear turquoise thing going on, which I didn’t expect this close to town.

The Tahoe Funship is kind of ridiculous in the best way — two decks and a slide that looks like something out of a backyard birthday party. My nephew dared me to go down first. The water was colder than I thought; I came up laughing and sputtering salt, and even my mom joined in (she never swims at home). We anchored near Caladesi Island where the sand squeaked underfoot and there were these tiny spiral shells everywhere. You could smell sunscreen mixed with something briny — maybe seaweed drying in the sun?

Our guide pointed out a couple of ospreys circling overhead and explained how Three-Rooker Bar just appeared one year, like Florida decided it needed another island. We wandered off for a bit of shelling — not much talking, just the sound of waves licking at our ankles and someone’s Bluetooth speaker playing faint country music from the boat. I tried to say “Caladesi” properly; Li laughed at my accent (fair enough). There’s something about being out there where you can see nothing but sky and water that makes you forget about your phone for once.

On the way back toward Honeymoon Island, we passed a family picnicking right on their paddleboards (how do people balance like that?). The sun started dipping lower but not quite sunset yet — everything went gold for a minute. It felt like time stretched out in all directions. I still think about that view sometimes when I’m stuck in traffic or scrolling through emails.

Step-by-step itinerary

Day 1 — Private boating and island exploration

• Attend safety briefing
• 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 at islands
• Enjoy Clearwater Beach activities

Top questions

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

This private boat tour accommodates up to 8 passengers per booking.

Is dolphin watching guaranteed during this tour?

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

Does the boat have a slide?

Yes, the Tahoe Funship features a slide from the upper deck into the water.

Are swimming and shelling stops included?

Yes, you’ll anchor at barrier islands for swimming, snorkeling, or shelling.

What locations does this Clearwater Beach boat tour visit?

The tour typically visits Caladesi Island, Honeymoon Island, and Three Rooker Bar.

Is pickup included for this private boat day?

Pickup and drop-off at a designated meeting point are included with your booking.

Are food or drinks provided on board?

A cooler with complimentary bottled water is provided; you may bring your own snacks or drinks.

Is this tour suitable for all fitness levels?

Yes, it’s suitable for all physical fitness levels.

What’s included

Your half-day includes pickup and drop-off at an easy meeting point in Clearwater Beach, your own professional captain handling navigation and safety gear for everyone onboard. There’s a cooler stocked with ice-cold bottled water waiting plus Big Joe floats if you want to drift awhile—and mesh bags so you can actually take those shells home without filling your pockets with sand.