Top Clearwater Private Sightseeing Tours

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.

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.

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.

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.

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.

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.

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.

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 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.

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.

* PRICE IS PER TANDEM KAYAK FOR 2 PEOPLE! * Skip the crowded group tours and experience Clearwater from the water at your own pace. This 2.5-hour private guided kayak adventure is reserved exclusively for you and your group. We’ll paddle from North Clearwater Beach through the calm Intracoastal Waterway, passing beautiful waterfront homes, tropical scenery and local wildlife on our way to a secluded spoil island. And this isn’t 2.5 hours of nonstop paddling. Once we reach the island, you’ll have about an hour to swim, explore, relax on the beach, play games, or simply enjoy being out on the water before we make our way back. Never kayaked before? Our kayaks are the most stable in the industry. We take care everything! Your experience includes towels, cold bottled water and snacks, a Bluetooth speaker for music, beach games and a cooler—so you can show up ready to have fun. Book your private kayak tour and come experience a side of Clearwater most visitors never get to see.

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.

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.

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.

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.

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.

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.

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!

Looking to make unforgettable beach memories this March? Available all month long, our St. Patrick’s Day beach photoshoot is perfect for couples, friends, families, and solo travelers who want stunning photos with expert posing guidance. This fun seasonal photoshoot is perfect for anyone wanting festive beach portraits with a St. Patrick’s Day feel, without needing to book on St. Patrick’s Day itself. In just 1 fun-filled hour, we will guide you through easy, flattering poses. No experience needed. Whether you're celebrating St. Patty’s Day, a spring getaway, or just want an excuse to throw on your green, we’ve got you. After your session, your photographer will deliver your favorite 8 edited digital images plus 1 FREE, with the option to purchase more. No pressure. No obligation. Just stunning memories with a festive St. Patrick’s touch. If you would like us to travel to your location for your session, please include that request in the Notes section when booking.

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!

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!

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!