Clearwater Beach: Private Dolphin & Island Boat Tour with Guide

Summary

Private boat trip to barrier islands with dolphin watching

You’ll cruise Clearwater Beach’s waterways by private boat with a local guide, spot wild dolphins up close, explore hidden corners of Caladesi and Honeymoon Islands, and float or swim at sandbars with all gear provided. Expect laughter, unexpected wildlife moments, and time to just breathe in the Gulf air.

What’s the experience like?

The first thing I remember is the slap of salty air as we pushed off from Clearwater Beach — not sharp, just that soft Florida warmth. Our captain, Mike, had this easy way about him; he pointed out a pelican perched on a post and joked that it was the real boss of the marina. I laughed, but honestly, it did look like it was judging us. The boat itself felt sturdy but open, perfect for six of us to stretch out without bumping elbows. There was bottled water in the cooler and some kind of mesh bags for shelling — I didn’t know what those were for yet.

We skimmed north along the coast, past houses that looked straight out of a movie. Then suddenly dolphins — two of them — arched right near our wake. Not staged or anything; they just showed up. Mike slowed down so we could watch them longer. The water here is this odd blue-green, almost glassy in spots, and you can smell sunscreen and seaweed mixed together. At Caladesi Island, we hopped off barefoot into sand that squeaked underfoot (I swear it does). I found a shell shaped like a tiny ear and kept it in my pocket for luck.

Honeymoon Island was next — more wild than I expected. There’s this pine forest right by the beach where you can hear ospreys calling overhead if you listen between the wind gusts. We didn’t see any manatees but someone thought they spotted one’s nose poking up (could’ve been driftwood). On Three-Rooker Bar, we anchored and floated around on these huge foam mats — Big Joe floats? My nephew tried to race me and lost spectacularly. The sun started dipping lower but nobody really wanted to leave yet.

I still think about how quiet it got out there when everyone stopped talking at once — just waves slapping the hull and gulls somewhere far off. It’s funny how a half-day can feel long enough to reset your brain. If you go, ask Mike about his favorite island story; he’s got plenty.

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
• Explore Honeymoon Island
• Visit Three-Rooker Sand Bar
• Swim, snorkel, or shell on islands
• Enjoy complimentary bottled water and floats
• Return to Clearwater Beach

Top questions

How many people can join the private boat tour?

The private boat tour accommodates 1-6 passengers per booking.

Is dolphin watching guaranteed on this Clearwater Beach boat tour?

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

Are swimming and shelling included during the tour?

Yes, guests can swim and go shelling on barrier islands such as Caladesi Island.

Does the tour include pickup from my hotel?

No hotel pickup is included; pickup is at a designated meeting point nearby.

What is provided on board during the boat trip?

A cooler with ice and bottled water, Big Joe floats for swimming, mesh shell bags for collecting shells, life jackets, fuel, safety equipment, and guidance from a professional local captain are all included.

What’s included

Your day includes pickup and drop-off at an easy meeting point near Clearwater Beach, all fuel costs covered, complimentary bottled water in an ice-filled cooler, use of Big Joe water floats for swimming stops, mesh bags for shell collecting on pristine islands like Caladesi or Honeymoon, plus all safety gear—and your own friendly local captain guiding every step.