Top Clearwater How to Get Around

Wildlife cruises are always a gamble when it comes to spotting animals—but during this boat ride along the emerald-green waters of Clearwater Beach, dolphin sightings are guaranteed. Relax onboard the comfortable, restroom-equipped boat as you take in the Gulf Coast’s picturesque scenery, listening to insights about the region’s history and natural heritage from guides along the way.

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.

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.

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.

Cruise out on the Gulf of Mexico and watch the sun dip below the horizon on this cruise from Clearwater. Sail along the Intercoastal Waterway, keeping an eye out for bottlenose dolphins and listening to commentary about your surroundings. Just as the sun is setting, guests 21 and older enjoy a champagne toast before sailing back to the dock.

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.

Ignite your sense of adventure and take your ride beyond the ordinary with the thrill of our jet car experience. Instead of simply cruising in circles, experience the excitement of pushing limits and mastering the water with energy, skill, and style. Feel the rush as you carve through the water and challenge yourself with every maneuver. Engineered for power, balance, and responsiveness, they provide the ideal combination of safety and performance, helping every rider maximize their adventure and create an unforgettable experience on the water.

Ignite your sense of adventure and take your ride beyond the ordinary with the thrill of our jet car experience. Instead of simply cruising in circles, experience the excitement of pushing limits and mastering the water with energy, skill, and style. Feel the rush as you carve through the water and challenge yourself with every maneuver. Engineered for power, balance, and responsiveness, they provide the ideal combination of safety and performance, helping every rider maximize their adventure and create an unforgettable experience on the water.

Freestyle jet skiing delivers an unmatched rush for anyone eager to take water sports to the next level. Feel the excitement as you ride across the waves, launch into the air, and perform impressive flips, spins, and daring tricks with confidence, balance, and style. Every ride is an opportunity to challenge yourself, improve your skills, and experience the thrill of complete freedom on the water. From experienced freestyle athletes to first-time riders seeking an unforgettable adventure, our premium high-performance jet skis are engineered to meet the demands of extreme riding. Built for power, agility, and control, they provide the perfect combination of speed and stability to help you maximize every jump, maneuver, and landing. No matter your skill level, you’ll enjoy an adrenaline-filled experience designed to create lasting memories and take your freestyle riding to new heights.

Spot dolphins and other marine life on this playful boat ride aboard a one-of-a-kind 50-foot shark-themed vessel. This specialized boat creates a mega wake that attracts dolphins, and the boat’s shark design is fun for all ages. While on board, you’ll hear interesting Clearwater Beach facts and stories, as you spot attractions and famous homes on land and dolphins in the water.

Spice up any Florida vacation with a cruise on Tampa Bay. Beginning in Clearwater, enjoy a beautiful sunset (depending upon the time of year) and listen to live music on board the elegant 'StarLite Majesty' yacht. Choose from one of the open-air observation decks or the climate-controlled dining cabin inside. For dinner (at own expense), choose from several delicious gourmet meal entrees along with salad, dessert, and coffee or tea. Then dance the night away or take a romantic stroll along the deck.

Clearwater has some of the best voted beaches in the United States and this exciting tiki tour is a great way to experience the Gulf waters. Hop aboard the only U.S. Coast Guard certified tiki boat in Clearwater Beach for a fun day under the sun. Perfect for celebrations, this cruise can hold over a dozen people for a party. An open bar with beers and cocktails is included.

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.

Experience Clearwater Beach like never before on your guided two-hour Dolphin Kayak and Island Excursion departing directly from Shephard’s Beach Resort. Paddle through calm Gulf waters as you search for wild dolphins, observe the natural beauty of Bird Island, and enjoy fascinating coastal history shared by local guides. Guests may also spot gentle manatees and sea turtles while enjoying Clearwater’s famous crystal-clear waters and shallow sandbars. Perfect for beginners, families, and adventure seekers looking for an unforgettable experience on the water.

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.

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.

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.

Many beaches, sandbars, islands, and backwater coves along Florida’s Gulf Coast are only reachable by boat—but some operators try to pack in as many travelers as possible, making a cruise feel more like a spin in a cramped elevator. Treat yourself to a deluxe experience on this private, chartered boat ride, whether that's swimming, picnicking, spotting bottlenose dolphins, or simply relaxing on deck to your own music—Bluetooth included.

Get ready for a relaxing day on the water with Captain Nick around Clearwater. Three Rooker Island, Dunedin, Tarpon Springs, and Caladesi Island State Park are all visible during your cruise to some secluded beaches only accessible by boat. Bring your own beverages to place in the cooler full of ice and fire up the grill for a barbecue on board if you wish. The tour can depart from Clearwater or Dunedin.

Enjoy a flexible, self-guided adventure on the water with this kayak or stand-up paddleboard (SUP) rental experience. Perfect for all skill levels, this rental allows you to explore scenic waterways at your own pace after a quick orientation and equipment setup. Paddle through calm estuaries and mangrove-lined routes, where you can take in the peaceful surroundings and spot local wildlife such as dolphins, manatees, and shorebirds. With high-quality equipment provided and easy-to-follow guidance before you launch, this experience offers a relaxing and accessible way to connect with nature, whether you're seeking a solo escape, a family outing, or a fun day with friends.

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.

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.