Top Clearwater Tours, Sightseeing & Cruises

Whether you're a seasoned pro or a first-time rider looking to test your limits, our high-performance jet skis are specifically designed to handle the demands of freestyle riding, ensuring you get the most out of your experience! Freestyle jet skiing is the ultimate adrenaline rush, combining skill, speed, and creativity on the water. It’s all about testing your limits and experiencing the thrill of high-energy water action like never before.

Take a tour of one of Florida's handful of wineries on this excursion in Clearwater. Follow your guide through a tour of the winery whilst you learn about wine production methods. Then, enjoy a tasting of three onsite-produced wines. Nibble charcuterie as you go to keep your palette neutral so you are able to pick up on the unique flavor profiles.

We provide the perfect 2 hour Floating Tiki Boat for any of your event needs… whether you're celebrating birthdays, anniversaries, graduations, retirements, or bachelor/bachelorette parties, we offer an unforgettable experience showcasing Clearwater Beach! Our spacious tiki boat is designed to accommodate up to 13 passengers, ensuring a comfortable experience. Equipped with a bathroom and Bluetooth speakers, we have everything you need to make your journey truly remarkable. For groups of more than 6, the captain is hired separately. We will provide a list of our favorite USCG-Qualified captains for you to hire after your reservation is complete. We strive to make your experience as enjoyable as possible, providing complimentary water and snacks on board, along with coolers filled with ice for your convenience and drinks.

Skip the crowded pontoon boats and step aboard a private 6-passenger Sea Ray designed for a more personal and unforgettable day on the water. Smaller, faster, and far more intimate than large tour boats, this experience lets you explore farther and enjoy the water the way it was meant to be. Relax, swim, and play with all the fun water toys included—from paddleboards and snorkel gear to the popular Bote Hangout floating dock, plus oversized pool noodles for ultimate lounging. Whether you're looking for a fun day with friends, a family adventure, or a laid-back cruise, this experience delivers comfort, flexibility, and a truly local vibe. The boat also includes an onboard restroom for added convenience so you can stay out on the water longer. And remember—it’s not just about the boat, it’s about the captain. Your experienced captain knows the best spots to explore, relax, and make the most of your time on the water.

Spend some time on the water with a fishing charter from Holiday, a town just a little north of Clearwater. You'll have the chance to fish in the Gulf of Mexico while admiring the coastal scenery, including Anclote Key Preserve State Park. Species you might catch include snook, tarpon, trout, and redfish, depending on the time of year. Even on windy days, there are many spots to fish.

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.

Take your booze cruise to the next level and hop on a floating tiki bar on Clearwater Beach. Gently float on the Gulf of Mexico while enjoying your favorite cocktail and admiring the natural landscape of Florida’s coast. Bring your choice of beverages and snacks on board and play your favorite tunes with the provided Bluetooth speaker for a relaxing day on the water.

Whether you're a seasoned pro or a first-time rider looking to test your limits, our high-performance jet skis are specifically designed to handle the demands of freestyle riding, ensuring you get the most out of your experience! Freestyle jet skiing is the ultimate adrenaline rush, combining skill, speed, and creativity on the water. It’s all about testing your limits and experiencing the thrill of high-energy water action like never before.

Get out on the water with a private 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. Depending on the conditions, that could be Caladesi Island State Park or Sand Key Park. Species you might catch include redfish, black drum, trout, cobia, and jack crevalle.

Looking to make beach memories? Our Express Photoshoot is perfect for couples, families, and solo travelers who want stunning photos with expert posing guidance in less time. In just 30 fun-filled minutes, your photographer will guide you through easy, flattering poses. No experience needed! Whether you're celebrating a milestone, marking your vacation, or just want beautiful sunset shots, we've got you. At the end of the session, your photographer will deliver your favorite 4 fully edited, digital images from the session, with the option to purchase more. No pressure. No obligation. Just stunning beach memories.

Learn all about the fishing and sponging industry in Tarpon Springs with this guided tour along the Florida city's Sponge Docks. You'll also learn all about the Greek-American community here in the city and even get to sip on thick, dark "mud coffee" while snacking on traditional Greek pastries.

Experience the charm of Downtown Dunedin on a small-group walking tour that blends history, culture, and local flavors. Uncover fascinating stories and unique highlights of this picturesque Main Street community along the Intracoastal Waterway. Indulge in delectable brunch, lunch, and drinks, including alcoholic beverages, and discover Dunedin’s vibrant scene in the most delightful way.

Explore the Anclote River on a guided kayak eco tour with a small group. Follow your wildlife expert guide as you paddle through the mangroves, keeping an eye out for wildlife such as dolphins, manatees, and bald eagles. Learn about the unique ecosystem and stop at the historic Tarpon Springs Sponge Docks along the way.

Experience Clearwater Beach like never before on a guided clear kayak tour! Paddle through the sparkling turquoise waters and explore the scenic waterways in a completely transparent kayak, offering unparalleled views of the underwater world. This is a family-friendly adventure is perfect for all skill levels. Keep an eye out for dolphins, manatees, and other fascinating marine life as you journey from the dock area to a beautiful sandbar. Our knowledgeable guides will share intriguing stories about the local ecology, wildlife, and the history of Clearwater Beach, making this an unforgettable experience.

2026 Besties Award-winning original Tarpon Springs ghost tour. So good it was copied. Led by Ace Chapman — and long story short, it never is. Now in its fourth year, this is the original Tarpon Springs ghost tour, led by screenwriter and longtime local guide Ace Chapman. The history is real, researched, and specific — never borrowed, embellished, or sold as a paid upgrade. The tour covers downtown Tarpon Springs after dark, including the story of Marshal Ruben Jones, a lawman whose career and mysterious 1921 death remain part of local legend. The route passes the Cheney House, the Old Dry Goods Store, and the Old Saloon Building, home to a 1953 film's famous fight scene. Guests use dowsing rods at the Train Depot and a spirit box along the way. There's also Mary, a spirit documented turning her streetlight on and off on demand. No fake equipment. No scripted theatrics. No paid upgrades. 2026 Besties Award winner, Best Tour. Still the best one.

2026 Besties Award-winning original Safety Harbor ghost tour, running since 2021. Led by certified guide Cynthia Dominick. Real history. No theatrics. Safety Harbor is a small coastal town on Tampa Bay. After dark, it tells a different story. This is Safety Harbor's only ghost tour and the longest running — founded in 2021 by Cynthia Dominick. With a 4.9-star Google rating and the 2026 Besties Award for Best Tour, Silent Slayer has built its reputation on real experiences, not theatrical ones. This 90-minute walking tour covers documented history and paranormal activity downtown, including a hanging tree, a devastating fire, and a bank robbery, with stops at the historic Safety Harbor Resort and Spa lobby. The tour begins near City Hall, where since 2021 Silent Slayer has documented a firetruck phenomenon with no explanation. Guests finish with a ghost hunting sampler at the Elf Tree and a stop at the ancient Baranoff Oak. No costumes. No actors. No scripted jump scares.

Skip the crowded pontoon boats and step aboard a private 6-passenger Sea Ray designed for a more personal and unforgettable day on the water. Smaller, faster, and far more intimate than large tour boats, this experience lets you explore farther and enjoy the water the way it was meant to be. Relax, swim, and play with all the fun water toys included—from paddleboards and snorkel gear to the popular Bote Hangout floating dock, plus oversized pool noodles for ultimate lounging. Whether you're looking for a fun day with friends, a family adventure, or a laid-back cruise, this experience delivers comfort, flexibility, and a truly local vibe. The boat also includes an onboard restroom for added convenience so you can stay out on the water longer. And remember—it’s not just about the boat, it’s about the captain. Your experienced captain knows the best spots to explore, relax, and make the most of your time on the water.

The Tampa Bay area is known for its saltwater fishing but for those who want a more relaxing experience, book this private bass fishing tour on Lake Tarpon. Meet your captain at the lake and spend a few hours or a whole day on the water trolling for largemouth bass. Whether you’re a visitor or a resident, this private experience is a great way to enjoy Florida’s wildlife and catch some fish.

Spend an unforgettable half-day exploring Clearwater’s islands and calm Gulf waters aboard Salt Therapy with Captain Clearwater. This 4-hour private cruise is the perfect balance of adventure and relaxation—see dolphins, visit sandbars, swim, snorkel, or anchor up for a floating picnic. Bring your own drinks and tunes while your USCG-licensed captain shares local stories and secret spots known only to Clearwater regulars. With flexible pickup points and a laid-back pace, this is how locals spend their day off: sun on your face, salt in the air, and time on your side. All Captain Clearwater charters are private, customizable, and flexible based on weather and guest preference. Highlights • Half-day (4-hour) private charter aboard Salt Therapy • Explore sandbars & barrier-island beaches • Dolphin watching & swimming stops • Cooler, ice & bottled water included • Pickup in Clearwater, Belleair & IRB Chase the sun, drop the anchor, and let island time take over—“Boat Like a Local.”

Experience Clearwater’s golden hour aboard Salt Therapy with Captain Clearwater. This 2-hour private sunset cruise is pure Florida magic—dolphins playing in the fading light, the sky painted in tropical color, and calm Gulf waters reflecting every shade of orange and gold. Bring your favorite drinks, cue up the music, and unwind as your USCG-licensed captain guides you to the best vantage points for sunset photos and dolphin sightings. Perfect for couples, families, or celebrations, this relaxing evening escape captures the coastal charm that makes Clearwater unforgettable. All Captain Clearwater charters are private, customizable, and flexible based on weather and guest preference. Highlights • Private 2-hour evening cruise on Salt Therapy • Watch the sunset over the Gulf of Mexico • Spot dolphins & enjoy calm coastal waters • Cooler, ice & bottled water included • Pickup in Clearwater Beach & Indian Rocks Beach Toast the sunset, feel the breeze, and end your day the Clearwater way.

Soak up some of Florida’s most spectacular beachy scenery, and enjoy a relaxing excursion out on the water, on this private boat charter. 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.

Embark on a sky-high adventure that will show you Clearwater from a whole new perspective. You’ll enjoy an unforgettable private helicopter ride with a professional crew that ensures your safety. Soar across Clearwater Beach’s sparkling blue water and white powder sand, enjoy a bird’s eye view of the famous Pier 60 fishing pier, and sweep above Florida’s first golf course at the scenic Bellair Country Club.

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 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.