About this experience
A Boat Day offers private, customized boat charters for small groups of up to 10 passengers. Sit back and relax on the very comfortable, 27 foot double-decker Funship with a slide, as you cruise the waterways with a Captain as your guide. Your boating adventure will get you up close to wild dolphins and take you to secluded barrier islands so you can go shelling on pristine beaches or swim in the Gulf of Mexico. Our private boat tours are perfect for family outings, birthdays, anniversaries, graduations, bachelorette parties, marriage proposals, romantic getaways, reunions, spreading ashes, or any other reason!
At a glance
- Duration: 4 hr
- Private experience
Planning perspective
How I’d plan this experience
If you want a Clearwater day that trades a fixed beach itinerary for time on the water, this four-hour private charter is a strong fit. I’d choose it for a family or small group that wants to mix cruising with swimming, shelling and wildlife-spotting, while keeping the day flexible. The main appeal is having a captain guide your group between the waterways and nearby barrier islands; the trade-off is that wildlife sightings and beach conditions are not something you can schedule.
Who I’d recommend it for
The private format suits a group that wants to spend the outing together rather than join a larger shared tour. The boat accommodates up to 10, and the double-decker Funship has a slide; I think that combination makes it appealing for mixed-age family groups as well as celebrations with friends. Traveller feedback also describes children, parents and grandparents enjoying the same trip, though every group’s comfort and interests will differ.
I’d be less inclined to choose it if your priority is a long, land-based visit to a particular island. The experience is built around cruising and making stops, not a guaranteed amount of time ashore at any one place.
Choose flexibility over a fixed checklist
The itinerary may head north toward Caladesi Island, Honeymoon Island and Three Rooker Sand Bar, with opportunities to swim, snorkel, shell or explore. Those are possibilities within a customized outing, not a promise that you’ll spend equal time at each stop. My advice is to tell your group what matters most—perhaps swimming rather than shelling—so you can make the most of the captain-guided plan without treating every listed place as a must-see.
Dolphins are described as very likely, while manatees, turtles, rays and other wildlife are possibilities. I’d treat sightings as a welcome bonus, not the sole reason to book.
Plan around the four-hour outing
Four hours gives the trip room for cruising and island stops, but it is still a half-day, not an all-day island stay. A cooler with bottled water, floats and mesh shell bags are included, and the charter includes life jackets and safety equipment. Pickup is arranged at a designated waterfront meeting point after reservation, so leave room in your plans for confirming where to meet rather than assuming a particular dock.
The real trade-off: open-water conditions
A boat-and-beach day depends on the weather. One account describes a windy, cold outing where the captain adjusted the sailing area, but that is not a guarantee that conditions will feel comfortable for every group. I’d bring layers and keep expectations flexible; the cancellation policy allows a full refund for cancellations at least 24 hours ahead and notes cancellation for bad weather.
Planning analysis informed by the tour itinerary and traveller feedback · Updated October 27, 2026
Plan your experience
Set aside 4 hr for the experience itself, with additional time to reach your meeting or pickup point.
Before you go
- Suitable for all physical fitness levels
Local guides to help you plan
Choosing a setting on Clearwater Beach
Think about open sand, a public promenade and the more animated beach center as different parts of the day.
Planning a Clearwater Beach day
Keep arrival, the beach interval and the return clear enough to leave the middle of the day flexible.
What is included
- Cooler with ice and bottled water
- Pickup and drop-off at designated meeting point
- Professional guide
- Island hopping and anchoring at sand bars
- Dolphin watching
- Private, custom boat tour
- Shelling and swimming
- Fuel
- Life jackets and safety equipment
- Local taxes
Not included
- Captain gratuity
Itinerary and highlights
Your BOAT DAY starts with a safety briefing, then it's time to cast off! Your trip will typically take you north of Clearwater Beach to our beautiful barrier islands including Caladesi Island, Honeymoon Island and Three Rooker Sand Bar. Along the way it is very likely that we will see dolphins. We may also see manatees, sea turtles, rays, Ospreys, native birds or other local wildlife. As your BOAT DAY continues, it is common for guests to get off the boat and go swimming and snorkeling, or shelling and exploring on our beautiful islands. Afternoon and evening tours can include watching the sun set from the boat, over the Gulf of Mexico. All guests will enjoy a cooler with complimentary bottled water, Big Joe water floats and mesh shell bags.
One of the few untouched islands along the Gulf Coast, Caladesi Island State Park is accessible only by boat, but is worth the extra effort.
One of Florida’s best-loved state parks, Honeymoon Island has more than four miles of beach to explore along with a three-mile trail through one of the last remaining virgin slash pine forests.
Three-Rooker Baris a small, semicircular island that has emerged within the last decade. The fact that sand has been accumulating at this location while erosion has occurred at other locations demonstrates the complexity of the coastal processes at work on the West-Central Florida coast. As the island emerged, it quickly became vegetated, increasing its stability.
Laid-back Clearwater Beach is known for its namesake stretch of soft, white sand, which draws visitors year-round for jet-skiing, parasailing, and stand-up paddle boarding in its calm waters.
Meeting and pickup information
- Once your reservation is complete we will contact you and coordinate the most covenient pickup location. It can be a public or private boat dock, a marina or other waterfront location.
Languages and tickets
- English — Guide
- Mobile Only
Tour operator
- A Boat Day
Accessibility and practical details
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- A maximum of 10 people per booking
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Questions about this experience
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Traveller reviews and photos
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