Top Clearwater Private Sightseeing Tours

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!

Take to the water and leave the crowds behind on this private, half-day boat tour led by a captain from Florida’s Clearwater Beach. Explore the coastline, look out for dolphins, and take a dip in the water before cooling off with ice cooler and bottled water included. Enjoy the flexibility to customize your itinerary with island hopping, stops at beach bars, sunbathing time, or more – it’s all up to you.

Experience the best of Florida’s coast aboard your own private boat. Charter this spacious boat for a half day and tell the captain what you’d like to see. Then, sit back and relax while you sail on the Gulf of Mexico in search of pristine beaches or idyllic swim spots. Book this experience for a special occasion or just a casual boat day.

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.

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.

* 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.

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.

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.

Have a relaxing, fun day aboard this double-decker boat for a tour led by an experienced captain, who can sail you to some of the best spots in the area with your private group. Explore peaceful barrier islands, slide off the top deck to take a dip, and try your luck spotting wild dolphins for an unforgettable four hours.

Turn up the music and turn down the lights — Clearwater from the water at night is absolutely stunning! Hop aboard our motorized party bike on water for a 2-hour private sunset cruise built for group fun, with a USCG-certified captain on board to steer while you and your crew pedal, party, and take in the views. As the sky fades into evening, enjoy sparkling night views of the water, passing boats, and beautiful waterfront homes along the bay. Dance, sightsee, and relax with your favorite drinks as our party lights set the mood for an unforgettable night on the water — there's no better way to experience Clearwater Beach after dark. This cruise is BYOB, so bring your favorite drinks and snacks along for the ride. With room for up to 20 guests, this private charter is perfect for birthdays, bachelorette parties, corporate events, or any celebration that calls for a big group and an even bigger vibe.

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

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.

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!

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.

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.