Top Clearwater Tours by Duration

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.

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.

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.

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.”

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.

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.

Experience one of the top-rated Clearwater Beach pontoon tours on a private boat tour for up to 6 guests. Cruise the crystal-clear waters of the Gulf of Mexico with a licensed captain while enjoying panoramic coastal views and dolphin sightings. Visit Caladesi Island State Park, Honeymoon Island, and popular sandbars like Three Rooker Island — accessible only by boat. Swim, snorkel, collect seashells, or relax in turquoise waters as your customizable itinerary is tailored to your group. Perfect for families, couples, and small groups, this private Clearwater Beach boat tour offers a relaxed, personalized Gulf Coast adventure focused on comfort, safety, and unforgettable island exploration. Why Travelers Love This Tour: • Private experience for up to 6 guests • Dolphin watching opportunities • Island stops & sandbar access • Swim, snorkel & shell • Flexible itinerary with licensed captain

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.

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.

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.”

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 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.

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.

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!

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!

Escape the crowds and soak up Clearwater’s coastal vibe on this private 2-hour cruise aboard Salt Therapy with Captain Clearwater. Perfect for couples, families, or friends, it’s the ideal way to unwind and enjoy dolphin sightings, hidden sandbars, and scenic waterfront views without spending the whole day on the water. Bring your favorite drinks, cue up the Bluetooth playlist, and let your USCG-licensed captain handle the rest. With flexible pickup points and easygoing pacing, this short escape delivers big Florida energy in a small window. All Captain Clearwater charters are private, customizable, and flexible based on weather and guest preference. Highlights • Private 2-hour cruise aboard Salt Therapy • See dolphins & explore sandbars • Swim, float, or just relax to your music • Cooler, ice & bottled water included • Pickup in Clearwater Beach & Indian Rocks Beach Drift, laugh, and let the Gulf set the pace—“Boat Like a Local.”

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 best of Clearwater Beach and cover a lot of ground on a guided Segway tour. Join your guide and small group for a roll down the boardwalk, across Causeway Bridge, Pier 60, and more. Enjoy commentary about the area from your guide, keep your eyes peeled for dolphins in the distance, and enjoy panoramic views while you ride.

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.

Jimbos Jumbo Food Tours isn’t just about eating—it’s an interactive, high-energy adventure that blends amazing street food, quirky local history, and lively competition. Our exclusive walking trivia game keeps guests engaged, with a mystery prize awaiting the winning team! With a mix of hidden gems, bold flavors, and non-stop laughs, we create an unforgettable experience that’s as entertaining as it is delicious! Plus, only on our tour will you learn the Secret Chant, a magical celebration of food and fun. So come hungry and munch your way through Safety Harbor’s tastiest spots while competing for foodie glory—only the sharpest minds and hungriest bellies can win! Big bites, big laughs, and unforgettable fun await! An unforgettable experience that’s as entertaining as it is delicious!

The Gulf Coast town of Dunedin may be small but it’s full of history. Discover the best of Dunedin on a small-group bike tour and discover landmarks like Hammock Park, Kellogg Mansion, the Fenway Hotel, and more. Listen to the town’s history from your guide and keep your eyes peeled for local wildlife while riding along the trail.

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.