Clearwater sunset pontoon cruise: Dolphins and barrier islands

Drift past dolphins as the sky turns color over Clearwater's barrier islands

A private 2-hour sunset pontoon cruise in Clearwater for up to six passengers, with stops at Caladesi Island and Honeymoon Island, a USCG-licensed captain, and all fuel and equipment provided. The boat departs during evening hours timed to catch the sunset, and all stops are flexible based on your group's preferences.

Step-by-step itinerary

Stops and time at each

1. Caladesi Island30m
2. Honeymoon Island30m
3. Clearwater Beachpass by

Sunset cruise with island stops

• Cruise along Clearwater Beach coastline
• Stop at Honeymoon Island for 30 minutes
• Stop at Caladesi Island for 30 minutes

The experience

The cruise starts with a USCG-licensed captain piloting a comfortable pontoon boat through calm Gulf waters as the light begins to shift. You'll pass Clearwater Beach's shoreline (the soft white sand and beachfront resorts visible from the water), then head out to the barrier islands where the real stops happen. Dolphins often appear during the evening hours, playing in the water nearby while you watch the sky transform.

Caladesi Island State Park comes first, a pristine stretch of white sand and clear water where you can step off the boat, swim, walk the shoreline, or simply sit on one of Florida's most untouched barrier islands. The stop runs roughly 30 minutes, though your group can adjust the time based on what you want to do. Honeymoon Island follows: another local favorite with calm waters and scenic views where you can relax on the sand or explore the beach. Both stops are flexible. The captain works with your preferences and the flow of the day.

Everything is handled: the captain, the pontoon boat, fuel, equipment, and a cooler with ice. No planning beyond showing up. The whole experience is built for small groups, up to six people, so it stays intimate and laid-back whether you're marking something special or just want a quiet evening on the water.

What’s included

• USCG-licensed captain.
• private pontoon boat for your group.
• fuel and all equipment.
• cooler with ice.

Before you book

Days and timesEvery dayDeparts at 18:30

Book up to12h before

GroupPrivate

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated 4 days ago

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyInfant seats availablePets welcomePublic transport nearby

Operated by ClearWake Watersports

Is this one for you?The boat picks you up from Clearwater, so if you're staying in the area without a car, you don't need to arrange separate transport to the water. The fixed 2-hour window and flexible island stops mean you can fit the sunset into an evening without committing to a full day away from your hotel or plans.

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

Can I swim at Caladesi Island and Honeymoon Island during the cruise?

Yes. Both islands have stops where you can swim, walk the shoreline, or relax on the sand. Caladesi Island State Park is known for its clear water and pristine beaches, and Honeymoon Island offers calm waters ideal for swimming. Each stop runs about 30 minutes and can be adjusted based on what your group wants to do.

What time does the sunset cruise depart from Clearwater?

The cruise is timed for sunset, so departure happens during evening hours. The exact time depends on the season and when the sun sets that day. Contact the operator for the specific departure time for your date.

How often do dolphins appear on this cruise?

Dolphins are often seen playing in the Gulf waters during the evening hours, particularly around the barrier islands. While sightings are common, they are wildlife and not guaranteed on every trip.

Is this cruise suitable for young children and infants?

Yes. Infants and small children can ride in a pram or stroller, and specialized infant seats are available. The pontoon boat is wheelchair accessible, and all areas and surfaces are accessible. The experience is suitable for all physical fitness levels.

What's included in the 2-hour cruise price?

The cruise includes the USCG-licensed captain, private use of the pontoon boat, fuel, all equipment, and a cooler with ice. You bring nothing except yourself and your group.