Top Clearwater Private Sightseeing Tours

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.

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.

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.

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.

We provide the perfect 2 hour Floating Tiki Boat for any of your event needs… whether you're celebrating birthdays, anniversaries, graduations, retirements, or bachelor/bachelorette parties, we offer an unforgettable experience showcasing Clearwater Beach! Our spacious tiki boat is designed to accommodate up to 13 passengers, ensuring a comfortable experience. Equipped with a bathroom and Bluetooth speakers, we have everything you need to make your journey truly remarkable. For groups of more than 6, the captain is hired separately. We will provide a list of our favorite USCG-Qualified captains for you to hire after your reservation is complete. We strive to make your experience as enjoyable as possible, providing complimentary water and snacks on board, along with coolers filled with ice for your convenience and drinks.

Looking to make beach memories? Our Express Photoshoot is perfect for couples, families, and solo travelers who want stunning photos with expert posing guidance in less time. In just 30 fun-filled minutes, your photographer will guide you through easy, flattering poses. No experience needed! Whether you're celebrating a milestone, marking your vacation, or just want beautiful sunset shots, we've got you. At the end of the session, your photographer will deliver your favorite 4 fully edited, digital images from the session, with the option to purchase more. No pressure. No obligation. Just stunning beach memories.

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.

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.”

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.

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.

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.

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 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.

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.

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.

Travel effortlessly from Orlando to the stunning Clearwater Beach, known for its award-winning, sugary white sands and serene, crystal-clear waters. This transportation service caters to all resorts, Airbnbs, and private homes in Orlando, ensuring a smooth and convenient journey. Upon arrival, explore a vibrant atmosphere filled with diverse dining options, from casual beach bars to fine eateries, making for a perfect day of relaxation and enjoyment by the sea. - Convenient pickup from your Orlando location, including resorts and private homes - Experience the beauty of Clearwater Beach without the hassle of driving - Enjoy a variety of restaurants, bars, and eateries near the beach - Perfect for families, friends, and beach lovers seeking a day of fun and sun

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.

Enjoy a fun-filled day on this double-decker boat with the help of a seasoned sea captain. Try your luck spotting wild dolphins, explore secluded barrier islands, and take the slide off the top deck to swim in the Gulf of Mexico. Your captain will guide you to some of the best spots in the area while you kick back and enjoy the ride with your loved ones.

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!

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

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.