Caladesi Island Tours and Tickets

Get away from the crowds and find your peaceful place off Clearwater Beach with this private pontoon boat rental. Keep your eyes peeled for dolphins out there for a treat. This flexible tour lets you bring your own food and drinks, then discuss with your captain where you want to go. Island hop, stop to collect shells, and possibly even stay for sunset- it’s up to you.

Soak up some of Florida’s most spectacular beachy scenery, and enjoy a relaxing excursion out on the water, on this private boat charter. Pick between half- and full-day itineraries; meet your guide at your preferred local address; and hop aboard the 27-foot (8-meter), double-decker boat. Depending on your preferences, you can visit barrier islands and comb for seashells, swim and snorkel, relax on board and spot wildlife, and more.

Discover the beautiful beaches and waterways of Florida’s Gulf Coast with ease on this half-day private boat tour. Stops include Caladesi Island, Anciote Key Preserve, and Honeymoon Island state parks, where you can relax on the beach and play in the water with the provided water floats and water mats.

Experience the best of Florida’s coast aboard your own private boat. Charter this spacious boat for a few hours or an entire day and tell the captain what you’d like to see. Then, sit back and relax while you sail on the Gulf of Mexico in search of pristine beaches or idyllic swim spots. Book this experience for a special occasion or just a casual boat day.

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!

Get out on the water and play however you please with this private chartered boat in Clearwater Beach. You’ll cruise out onto the Gulf waters with your crew, bringing along as many as five guests. Wakeboards, wake surfboards and inflated tubes are all on the boat for your use. Tow your friends or catch waves on your board while admiring the coastal views and soaking up the sun.

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!

Explore the Florida coast aboard your own boat with this half- or full-day charter. Sit back and relax as your guide takes you past barrier islands and unspoiled beaches on the Gulf of Mexico. Spend your day basking in the Florida sun, swimming in the warm waters, and searching for local marine life. This rental is great for special occasions or just a fun day on the water.

Enjoy the exclusivity of a private boat trip for you and your party during this half- or full-day excursion. Your captain guides you through waterways for up-close views of wild dolphins and stops at secluded islands where you have time to relax on pristine beaches and swim in the Gulf of Mexico. Feel free to customize the itinerary with your captain to suit your group's interests. Price is per boat.

Come see the best of Clearwater on a PRIVATE boat tour! Along the pristine beaches of Clearwater, Honeymoon Island, and Caladesi Island, we will look for dolphins, anchor at local sand bars, go shelling, swimming & soak up some sun. Keep your eyes peeled for local wildlife like dolphins, ospreys, pelicans, cormorants & seagulls. Book this private boat charter for a special occasion or a casual family vacation day. We take up to 6 people of all ages & we can customize the travel speed & location stops. Let's face it - Grandma may not want to get off the boat, but the kids definitely want to go swimming. We get it! And we cater to everyone's wants. Yes, we allow alcohol on board, so bring your favorite snacks & drinks (please see our specific exclusions).

A BOAT DAY offers private, customized boat charters for small groups of 1-6 passengers. Sit back and relax on the very comfortable, 24 foot Hurricane Deck Boat 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, bachelor(ette) parties, marriage proposals, romantic getaways, reunions, spreading ashes, or any other reason!

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!

Spend a fun day out on the water aboard the Funship during this excursion from Clearwater, Florida. Board your private vessel, complete with a built-in slide, and explore the waterways, islands, and beaches. Whether you want to soak up the sun, swim, shell on nearby beaches, or even go snorkeling, your day is spent how you want it.

Discover the beautiful scenery of Florida’s Gulf Coast with ease on this half-day private eco boat tour from Holiday. Go island hopping, with stops at Caladesi Island, Honeymoon Island, and Anciote Key Preserve state parks, where you can relax on the beach, play in the water, and look for shells, wildlife, and historical sites.

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!

Embark on an exclusive private pontoon excursion from Clearwater Beach for a group of up to 6 people, setting off on a captivating journey to explore two of Florida's hidden gems: Caladesi Island and Three Rooker Bar. Cruise through the shimmering waters of the Gulf of Mexico aboard your luxurious pontoon, soaking in panoramic views of the coastline. Bring your snorkeling gear and upon arrival at Caladesi Island, dive into the pristine turquoise waters among vibrant marine life or stroll along the secluded shoreline, collecting shells and basking in the sun's warmth. Next, venture to Three Rooker Bar, a tranquil sandbar oasis accessible only by boat, where you'll indulge in a leisurely picnic on the soft white sands, surrounded by the serenity of the Gulf. With personalized service and unparalleled natural beauty, this excursion promises an unforgettable day of exploration and relaxation for all.

On this cruise you will experience dolphin sightings, as well as potentially seeing other wild-life such as manatees and sea turtles. You will get a tour of many cool attractions on Clearwater beach such as celebrity homes. You will have options of many waterfront restaurants to dock at for lunch and dinner while on your cruise. You will stop at beautiful islands, beaches and sandbars like Caladesi Island, Bird Island, 3 Rooker Island, One Tree Island and Honeymoon Island. And your cruise will end with one of Clearwater Beaches award winning sunsets. There are many options for things to do and see while on the cruises. And choosing different islands, restaurants and types of wild-life to view will depend on the customers preference. The captain will make sure the cruise is unique for each customer, and will do the best to let the customer decide what they would prefer to do on their cruise.

Get out on the water with a fishing charter from Clearwater. You'll have the chance to try your luck at fishing in the Gulf of Mexico while admiring the coastal scenery, including Caladesi Island State Park, which is only accessible by boat. Species you might catch include redfish, black drum, trout, cobia, and jack crevalle. Even on windy days, there are many spots to fish.

Come join us for our amazing Relax & Shred activity! It's the perfect opportunity to have a blast on the water while enjoying the best of both worlds. Picture yourself chilling out on our awesome pontoon party boat, soaking up the sun and taking in the beautiful views. But that's not all - for those who crave more excitement, you can also tear up the waves with some thrilling water sports like wake surfing, wakeboarding, or water tubing from our high-performance AXIS wake boat. Here's the best part: you don't have to choose between the two! Our unique setup allows you to switch between the pontoon party boat and the wake boat, so everyone gets a chance to experience both incredible options. But that's not all - we also make sure to give you some well-deserved beach time. We'll take you to a lovely island beach where you can truly live like a local for a day. So grab your friends, and family, or even make some new ones, and join us for this unforgettable day of fun in the sun!