Top Clearwater Cruises & Sailing

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.

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 double-decker catamaran 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.

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.

50-foot shark themed vessel. The only shark that dolphins love, producing a "MEGA" wake that dolphins love to jump and play in. Covered vessel with sun area. Padded seats and restroom.

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. The evening cruise includes a DJ and dancing.

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.

Embark on a scenic journey to find bottlenose dolphins on this dolphin-watching cruise near Clearwater in Florida. From Clearwater Bay to the turquoise waters of the Gulf of Mexico, enjoy the incredible views along the Intracoastal Waterway. See and hear about the celebrity mansions on the coast, and listen as the captain shares interesting facts about the natural wonders of the Gulf Coast region. Snacks and beverages are available for purchase on board. Dolphin sightings are guaranteed on this exciting tour.

Take your booze cruise to the next level and hop on a floating tiki bar on Clearwater Beach. Gently float on the Gulf of Mexico while enjoying your favorite cocktail and admiring the natural landscape of Florida’s coast. Bring your choice of beverages and snacks on board and play your favorite tunes with the provided Bluetooth speaker for a relaxing day on the water.

Climb aboard a schooner for an afternoon of sailing in Clearwater Beach with this tour. Enjoy sea breezes and admire views of the coastline 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.

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.

Enjoy an afternoon on this narrated 2-hour sightseeing cruise along Tampa Bay and Clearwater’s beautiful inland waters. On board the elegant 'StarLite Majesty' yacht, choose from the open-air outer deck or if it’s too warm, select the climate-controlled cabin inside. Either way, soak up the views and if you choose, you can add on lunch once you're aboard the vessel. Listen as the captain points out the area’s popular landmarks and history and look for dolphins and other wildlife on the journey.

Depart from our beautiful Holiday Inn at Indian Rocks location with one of our guides! We will take you down the beatiful intercoastal Indian Rocks beach up to a more open area. There, our guides will let you go out and enjoy a thrilling experience on the jetski up and down the coast of Indian Rocks & Clearwater Beach!

***Please arrive 30 minutes prior to your booking*** With the best Captains in the business, our staff members will show you the coast of ClearWater Beach, with our dolphin friends just swimming alongside of you. Sit down and relax on our brand new tour boat while we take you for an amazing tour! This tour is nothing shy of breathtaking. Come make memories that will last a lifetime with your friends and loved ones.

Get away from the crowds and find your peaceful place off Clearwater Beach with this private pontoon boat rental. Keep your eyes peeled for dolphins out there for a treat. This flexible tour lets you bring your own food and drinks, then discuss with your captain where you want to go. Island hop, stop to collect shells, and possibly even stay for sunset- it’s up to you.

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.

***Please arrive 30 minutes prior to scheduled departure time*** Get ready to enjoy your drinks in the best way on the Gulf. Once you board our brand new TIKI Boat, our Captains will show you the beautiful coast of Clearwater Beach like you have never seen before. This is a Bring Your Own Booz Cruise (BYOB) We can do just about everything except serve you your drinks! Head over to our website and book your BYOB TIKI Cruise today! ***Please complete the following waivers prior to your arrival***

Clearwater Beach is well-known for its amazing sunsets, though there’s plenty of equally exciting activities to enjoy when the sun is shining. Jump on this fun boat and sail out into Clearwater’s Gulf waters. You’ll glide around the shoreline with your captain pointing out landmarks and celebrity houses. Then, stay aboard for a souvenir shelling experience. No matter how good your searching skills are, everyone will take home seashells and sharks teeth.

We provide everything you need for an enjoyable and successful day on the water. This includes first class service, a clean and safe boat, a knowledgeable and personable captain, all of the needed fishing supplies (rods, reels, tackle, bait, and chum), as well as complimentary water and sunscreen. We provide a safe and enjoyable experience for anglers of all ages and experience levels. Kids are always welcome and encouraged on board.

The desert plays a huge part in Dubai’s culture and this safari helps you to experience the best of it. Enjoy a thrilling dune bashing session in a 4x4 with an experienced driver. Then, slide down a giant sand dune on a sandboard for stunning views of the desert. A camel for a relaxing ride around the dunes. Enjoy traditional pastimes like shisha smoking and henna hand painting, plus pose for pictures in historic dress. As the sun sets, feast on barbecue and take in a tanoura dance and fire show.

Sea Paradise Charters will take you on this private cruise to the best spots on the water to see Clearwater Beaches award winning and breathtaking views, sandbars and marine life. Let us be the highlight of your vacation! Sit back and relax! You'll enjoy fun, laughter, & magnificent sites you've never imagined while making lasting memories! We are experts at finding dolphins on the cruise, and you'll get amazing pictures of your amazing cruise that you can keep forever! Captain Trevor holds a Master United States Coast Guard License. He brings with him experience and knowledge of the Clearwater Gulf Coast ensuring you'll have an extraordinary boat ride. His passion for boating, nature, and marine life guarantee he will help you make the most of your guided tour. He will even help you design your dream cruise!

We are a family owned boat tour operator in Madeira Beach. We specialize in private boat tours to secluded sandbars and barrier island beaches. Along the way we'll see dolphins, local wildlife and beautiful waterfront homes. Once anchored at your beach of choice you can indulge in shelling, a leisurely beach walk and swimming in the clear blue waters. Your're welcome to bring your own snorkel equipment. Our goal is to make you safe, comfortable and to have fun engaging in the activities you choose. It's going to be a special day you won't forget.

A BOAT DAY offers private, customized boat charters for small groups of 1-6 passengers. Sit back and relax on the very comfortable, 24 foot Hurricane Deck Boat 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, bachelor(ette) parties, marriage proposals, romantic getaways, reunions, spreading ashes, or any other reason!

Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island or Sunset Cruises. 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 above the tranquil Gulf waters. And for an escapade to remember, join us on our Caladesi Island Tours, where untouched nature meets serenity. Let Fins Up Clearwater be your guide to unforgettable moments and endless wonder along Florida’s stunning coastline.