Top Clearwater Tours by Duration

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.

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.

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.

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.

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.

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.

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.

You will hear firsthand accounts of murders and other serious crimes that have occurred over time, all within and around the Tampa Bay area. Your tour guide has over three decades solving crimes and making arrests in the Tampa Bay area. This is not like other tours because you will hear inside details of the information that was not disclosed to the public and press. Get ready to put your detective skills to use. Your guide will take you to hidden gems that only locals know about. You will laugh and cry and have an adventure that is so much fun, it’s criminal. Rain or shine, the mystery awaits you. Come step on board and prepare for a day of nonstop intrigue. The Wine and True Crime tour is a perfect way to celebrate a birthday, girls’ night out, Bachelorette Party, Divorce Party or any other celebration!

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.

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.

Set out on Salt Therapy with Captain Chris, a U.S. Coast Guard veteran with over 40 years on the waters of Clearwater and the Gulf Coast. This 5-hour private charter lets you experience Florida’s west coast the way locals do—with freedom, sunshine, and salty smiles. Swim at hidden sandbars, hunt for shells on quiet islands, or watch dolphins race the wake through the Intracoastal. Whether you’re floating, exploring, or relaxing to your favorite playlist, this trip moves at your pace. With flexible stops, multiple pickup points, and a laid-back atmosphere, it’s the perfect blend of sightseeing, island time, and good company. All Captain Clearwater charters are private, customizable, and flexible based on weather and guest preference. Highlights • 5-hour private charter aboard Salt Therapy • Swim, explore, and dolphin-watch • Visit hidden islands & sandbars • Cooler, ice & bottled water provided • Pickup in Clearwater, Belleair & IRB Spend the day chasing sunshine—“Boat Like a Local.”

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.

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.

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!

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 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.

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!

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.

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.

This isn’t a cookie-cutter food tour — its begins on the highest roof top bar (10th Floor) on Clearwater Beach, with a full-on bride tribe experience. Guests enjoy an all inclusive event with food and alcoholic drinks, a hilarious Bachelorette Trivia Challenge (complete with a secret prize), a Scavenger Hunt for Charlie the Chicken, and even learn our famous Pre-Marital Celebration Chant that turns heads wherever we go! Our Bachelorette Mimosas, Munchies & Fun Food Tour is Clearwater Beach’s ultimate pre-wedding party on foot — where every sip, bite, and life time memories are created. - Explore Clearwater Beach's top beach food & drink spots with an enthusiastic guide. - Engage in a hilarious marriage trivia with a surprise gift for the winning team. - Customizable to your theme! - ADA-friendly tour.

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.

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.”