Clearwater Beach: Private Pontoon Boat Tour & Island Stops

Summary

Private boat trip from Clearwater to wild islands and secret sandbars

You’ll feel the Gulf breeze as you set out from Clearwater Beach with your own captain, stop at Caladesi Island for shell hunting or swimming, and maybe spot dolphins or manatees along the way. Bring your favorite drinks—there’s ice and water waiting—and settle in for an easygoing day where everything slows down.

What’s the experience like?

The first thing I noticed was the hum of the pontoon’s engine mixed with gulls overhead—kind of soothing, honestly. Captain Nick handed us cold bottles of water as we stepped on board near Clearwater Beach, and I remember thinking how much better this felt than a crowded ferry. He asked what we wanted out of the day, which caught me off guard (in a good way). We all sort of blurted out different things—shells, dolphins, just floating—and he just grinned and said, “We’ll see what the Gulf gives us.”

We drifted past Dunedin’s little marinas and then out toward Caladesi Island. The water turned that weirdly clear blue-green you only get in Florida. When we anchored by the sandbar, there was this warm breeze carrying hints of sunscreen and salt. I waded in up to my knees—softest sand ever—and found two perfect shells right away. At one point, someone spotted a manatee’s nose poking up for air. Everyone got quiet for a second except Captain Nick, who told us about the time a dolphin tried to steal his lunch (he swears it happened).

Lunch was whatever we brought—BYOB means you really can bring anything—and we used the cooler full of ice like it was gold. If you want to grill, apparently there’s a BBQ on board (we didn’t try it but next time…). There were some inflatable things for floating if you’re into that. The sun kept shifting behind clouds so sometimes it felt almost chilly for June; I kind of liked it though. The whole trip had this unhurried pace—nobody rushing us back or herding us around. Just salt air, laughter, and that feeling you get when you realize you’ve lost track of time completely.

Step-by-step itinerary

Day 1 — Private pontoon boat tour and island visits

• Board pontoon and review safety
• Customize trip route and plans
• Explore Caladesi Island and sandbar
• Relax, sunbathe, and watch sea life
• Visit Three Rooker Island for snorkeling
• Collect seashells and observe wildlife

Top questions

Is this Clearwater Beach pontoon boat tour private?

Yes, each tour is a private charter for your group only.

Does the tour include stops at Caladesi Island?

Yes, most trips include anchoring near Caladesi Island or nearby sandbars.

Can we bring our own food and drinks?

Yes, all trips are BYOB and you can bring any food or drinks you'd like.

Is snorkeling gear included?

Snorkeling gear is available for an extra cost on 4+ hour tours; otherwise bring your own.

Are service animals allowed on board?

Yes, service animals are permitted during the tour.

Is hotel pickup included?

No hotel pickup is included; you'll meet at the marina near Clearwater Beach.

What should I bring on this boat tour?

Bring food, drinks (if desired), sunscreen, swimwear, towels, and snorkeling gear if not renting.

How long does the pontoon boat tour last?

Tours vary in length; sunset tours are 2 hours while others can be longer by request.

What’s included

Your day includes bottled water waiting on board, a big cooler packed with ice for your drinks or snacks (BYOB style), Bluetooth radio for music if you want it loud or soft, plus an inflatable ring if you're out longer than four hours. If grilling is your thing and you've booked enough time, there's even a BBQ available—just ask ahead and bring what you want to cook. Snorkeling gear can be arranged for longer tours too.