Top Clearwater Sightseeing Tours

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.

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.

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.

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.

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.

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.

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters of Clearwater Beach. Welcome aboard the ultimate coastal adventure with Fins Up Clearwater! Dive into the crystal-clear waters of Clearwater Beach and let us whisk you away on a journey of discovery and delight. Embark on our exhilarating Sandbar Tours, where you can explore hidden treasures and pristine shores. Glide through the waves on our Dolphin Cruises, witnessing these majestic creatures in their natural habitat. Experience the breathtaking beauty of a Sunset Cruise as the sky paints a masterpiece. Let Fins Up Clearwater be your guide to unforgettable moments and endless wonder along Florida’s stunning coastline.

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.

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!

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.

Escape the crowded group tours and experience Clearwater from the water on a more personal island adventure. Paddle across the beautiful Intracoastal Waterway to a secluded spoil island, where you’ll have time to explore, search for shells, play beach games, relax and enjoy your favorite music. Along the way, keep an eye out for dolphins, manatees and other local wildlife that frequently call these waters home. Our comfortable, stable kayaks make the trip enjoyable for both first-time and experienced paddlers. With a relaxed pace, personalized experience and plenty of island time, this isn’t just a kayak tour — it’s a chance to experience Clearwater like a local.

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.

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.

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.

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!

This boat is all yours! Turn up the music and turn down the lights because Clearwater at sunset is absolutely stunning. There is no better way to enjoy the bay than sightseeing, dancing, and relaxing with your favorite drinks on our comfortable boat. We have a great Soundsystem on board you can connect to and party on. Stunning views and our party lights make this night cruise a blast! Since it's private to your group, we could even stop at the tiny island for a beach party if you choose. The Clearwater Night Cruise last two hours. Bring anything you would like to eat or drink (BYOB) for the tour as well as ice for your drinks. This boat is motorized, so pedaling is not an option but dancing is! A restroom is included on the boat for your convenience. The boat is a catamaran meaning that it rides smoothly though the waterway. Keep a keen eye out for dolphins that frequent these waters. For groups that just want to party, we pump up the music and all you have to do is enjoy the ride!

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.

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.

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.

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.

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.

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!

Embark on an unforgettable adventure with ParrotDise Express Boat Tours, offering premier Dolphin Excursions and captivating Sunset Tours in Clearwater and Dunedin. Cruise aboard the 47-foot ParrotDise Express, specially designed for optimal dolphin sightings, as you navigate stunning coastal waters. Experience wild dolphins up close while enjoying breathtaking views of Clearwater Beach and nearby islands. Ideal for families and friends, these tours also include complimentary beverages and opportunities for snorkeling and shelling. Discover the natural beauty and marine life of Florida’s Gulf Coast on this 2.5-hour journey. - Enjoy dolphin watching and sunset views on a 2.5-hour cruise - Complimentary alcoholic and non-alcoholic beverages included - Encounter dolphins in their natural habitat along scenic waters - Perfect for families, groups, and special occasions