Top Clearwater Adventure Tours in 2026

Hop aboard Clearwater’s ultimate dolphin-spotting boat tour. This high-speed adventure lets you cover more of the Gulf—and increases your chances of seeing dolphins up close as they play and surf in the wake. Cruise past celebrity homes and coastal landmarks on this powerful 73-foot vessel captained by seasoned pros.

Experience one of the top-rated Clearwater Beach pontoon tours with private 2-hour and 4-hour options for up to 6 guests. Choose our 2-hour evening sunset cruise for a relaxing ride along the coast as you watch the sun set over the Gulf. Looking for more adventure? The 4-hour tour gives you time to explore local favorites like Caladesi Island, Honeymoon Island and Three Rooker, with opportunities for swimming, snorkeling, shelling, sandbar stops and wildlife sightings. With no crowds and a flexible itinerary, your licensed captain takes care of the details while you enjoy your favorite food, drinks and music. A large cooler with fresh ice and a premium Bluetooth sound system are provided. Perfect for families, couples and small groups looking for a personalized Clearwater Beach boating experience.

Take a daytime or evening cruise around Clearwater, Florida aboard the Calypso Queen. A lunch or dinner buffet, as well as an open bar featuring rum punch, wine, and beer, is included. A full bar and dessert available for purchase. The evening cruise includes a DJ and dancing.

Climb aboard a schooner for an afternoon of sailing in Clearwater Beach with this tour. Enjoy sea breezes and admire views you wouldn't get if you stayed on shore during this scenic cruise. Keep an eye out for wildlife like dolphins and manatees during the sail. Guests are permitted to bring alcoholic beverages on board the schooner. Note that hard soled shoes are not allowed onboard for safety.

Dolphin encounters are quite common in the Gulf of Mexico, but this boat tour lets you get a closer look at them. Sail out towards Compass Island and keep your eyes peeled for the playful creatures while your captain provides commentary about your surroundings. Then, once you reach the island, jump in the water to search for marine life, collect shells, or simply enjoy the water.

The Gulf of Mexico is known for wild dolphin sightings and this tour from Clearwater Beach helps you discover the pods. Climb aboard the Little Toot, a tugboat-style boat, that creates a big wake that dolphins like to play in. While you’re out on the water, enjoy lively commentary about the dolphins and the surrounding area.

Paddle around Clearwater Beach with the help of a guide to help you spot some amazing local wildlife as you soak up the sights of the sea. Keep your eyes peeled for dolphins and manatees from your transparent kayak while your CPR and first-aid-trained tour leader helps you make memories to last a lifetime.

Embark on a scenic journey to find bottlenose dolphins on this dolphin-watching cruise from Clearwater in Florida. Enjoy the incredible views along the Intracoastal Waterway, passing celebrity mansions while listening to the captain’s commentary. Snacks and beverages are available for purchase on board. Dolphin sightings are guaranteed on this exciting tour—in the unlikely event you don’t see them, you can take another cruise at another time for free.

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.

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.

Experience the water like never before on this glowing nighttime kayaking adventure! Paddle across the water in a vibrant LED-lit clear kayak, lighting up the water beneath you as you glide under the evening sky. Customize your kayak with your favorite color or switch to a dazzling light show that creates an unforgettable atmosphere on the water. Whether you choose to paddle solo or share a tandem kayak, this experience is perfect for couples, families, and friends alike. Keep an eye out for local wildlife and peaceful nighttime scenery as your expert guide leads the way, ensuring a safe, fun, and memorable journey!

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.

Experience an unforgettable journey from the Intracoastal Waterways of Clearwater Beach, to Three-Rooker & Honeymoon Islands, with one of our professionally trained guides. As you skim near the mysterious mangrove forests, be thrilled by eco-sensitive encounters with dolphins, manatees, native birds and other diverse wildlife residing in the mangroves. Your expert tour guide will highlight interesting facts about nature and the geography of the region, or just let you rip it up!!

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.

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.

Watch as day turns into night off the coast of Florida on this sunset cruise from Clearwater. Enjoy the scenery and peaceful calm of a late-afternoon cruise on board a vessel with plenty of space to stretch out and soak up the breathtaking view. Watch a beautiful Florida sunset as the sun glows and gently settles into the Gulf of Mexico. Toast the new evening with a glass of Champagne.

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.

Discover the Florida coast from a different perspective on a private helicopter tour from Clearwater Airpark. Get a bird’s-eye view of beaches, state parks, lakes, and waterfront mansions over the course of your flight. Listen to commentary from your pilot and enjoy uninterrupted views of the area, so you can capture memories of your flight.

* PRICE IS PER TANDEM KAYAK FOR 2 PEOPLE! * Skip the crowded group tours and experience Clearwater from the water at your own pace. This 2.5-hour private guided kayak adventure is reserved exclusively for you and your group. We’ll paddle from North Clearwater Beach through the calm Intracoastal Waterway, passing beautiful waterfront homes, tropical scenery and local wildlife on our way to a secluded spoil island. And this isn’t 2.5 hours of nonstop paddling. Once we reach the island, you’ll have about an hour to swim, explore, relax on the beach, play games, or simply enjoy being out on the water before we make our way back. Never kayaked before? Our kayaks are the most stable in the industry. We take care everything! Your experience includes towels, cold bottled water and snacks, a Bluetooth speaker for music, beach games and a cooler—so you can show up ready to have fun. Book your private kayak tour and come experience a side of Clearwater most visitors never get to see.

While most people take to the seas for their views of the Florida coast, this private helicopter tour shows you the area from a different perspective. Board a helicopter and get a bird’s-eye view of Tampa Bay and its surroundings while you fly. Your dedicated pilot points out important landmarks, like Sunshine Skyway Bridge and downtown St. Petersburg, and provides commentary in the air.

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.

Experience a Relaxing Sunset Cruise in Clearwater for groups up to six End your day on the water with a private 2-hour sunset cruise along Clearwater’s beautiful barrier islands. This laid-back experience is perfect for couples, families, or small groups looking to unwind and take in one of Florida’s most stunning coastal sunsets. Cruise through calm Gulf waters as the sky transforms with vibrant colors, creating the perfect backdrop for photos and unforgettable moments. Keep an eye out for dolphins, which are often seen playing nearby during the evening hours. With a comfortable pontoon boat, a USCG-licensed captain, and everything provided—including fuel, equipment, and a cooler with ice—you can simply relax and enjoy the ride. Whether you're celebrating something special or just want a peaceful evening on the water, this sunset cruise is an easy, memorable way to experience Clearwater from a whole new perspective.

Enjoy a private 3-hour sunset cruise along the Clearwater Gulf Coast, designed exclusively for up to 4 guest. Relax aboard a comfortable private boat while taking in Clearwater's coastline and watching the sun set over the water. With a private experience and no other guest on board, you can enjoy the evening at your own pace. - Private boat experience for up to 4 guests - 3-hour sunset cruise - Relaxed, scenic experience along the Clearwater coastline - Ideal for couples or small groups seeking tranquility - Enjoy the scenic beauty of Clearwater's sunset