Top Clearwater Cruises & Sailing

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.

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.

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.

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.

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.

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.

See wild dolphins in the Gulf of Mexico on this relaxing dolphin-watching tour. Board your catamaran at a central location in Clearwater and head out on the gulf to search for wild dolphins. While you wait for them to come out and play, enjoy a delicious ice cream under the shade of the boat. Your captain provides about the local wildlife as well as your surroundings.

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.

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.

Enjoy the exclusivity of a private boat trip for you and your party during this half- or full-day excursion. Your captain guides you through waterways for up-close views of wild dolphins and stops at secluded islands where you have time to relax on pristine beaches and swim in the Gulf of Mexico. Feel free to customize the itinerary with your captain to suit your group's interests. Price is per boat.

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.

Experience the best of Florida’s coast aboard your own private boat. Charter this spacious boat for a few hours or an entire 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.

Zip through the waterways of Clearwater Beach aboard a private jet boat. Create an itinerary with your captain and visit several locations like Caladesi Island, Honeymoon Island, and the Intercoastal Waterway. Spend your day swimming, snorkeling with provided equipment, soaking up the warm Florida sun, dolphin watching, or sightseeing, the choice is yours.

THE PRICE IS FOR A 4-HOUR BOAT CHARTER AND INCLUDES UP TO 8 PEOPLE IN YOUR GROUP. A Boat Day offers private, customized half-day and full-day boat charters for small groups of up to 8 passengers. Sit back and relax on the very comfortable, 25 foot double-decker Funship 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 charters are perfect for family outings, birthdays, anniversaries, graduations, bachelor(ette) parties, marriage proposals, romantic getaways, reunions, spreading ashes, or any other reason!

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.

Soak up some of Florida’s most spectacular beachy scenery, and enjoy a relaxing excursion out on the water, on this private boat charter. Pick between half- and full-day itineraries; meet your guide at your preferred local address; and 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.

-A 2 hour Daysail is the perfect way to enjoy our smooth afternoon sea breeze as it powers us along the coast of Clearwater Beach. Whether you are a seasoned sailor or if this is your first time sailing, the Schooner Clearwater will be a memorable visit. - IMPORTANT- plan to arrive 45 minutes before departure time for mandatory check in to collect your boarding passes. We require a timely check in to report our passenger count for the USCG and to ensure everyone enjoys a 2-hour cruise -Our USCG credentialed Captain & Crew will welcome you on board like an old friend and treat you to a relaxed memorable visit. -Expect a 5 Star "True Sailing Experience" on our 52' custom steel Schooner sailing vessel. -Our motto is "We SAIL and We SAIL Well"!

Whether you're in the mood for a sandbar party, dolphin watching, or just relaxing, your trip is completely custom. An experienced Captain will be provided, enabling you to sit back and enjoy a safe and relaxing day on the water. Clearwater is home to Bottlenose Dolphins who love to play behind the boats. You may also see Manatees, Sting Rays, and more! The barrier islands, such as Caladesi Island and Three Rooker Island, can only be accessed by boat. This means less crowds, social distancing to the max, and blissful tranquility.

The Tampa Bay area is known for its saltwater fishing but for those who want a more relaxing experience, book this private bass fishing tour on Lake Tarpon. Meet your captain at the lake and spend a few hours or a whole day on the water trolling for largemouth bass. Whether you’re a visitor or a resident, this experience is a great way to enjoy Florida’s wildlife and catch some fish.

Offering fun on the water with private charters for up to six people. Whether your looking for a fun day at the beach, fishing, watching the sunset, or just going for a stroll on the water...you adventure awaits.

Set sail on the Gulf Coast aboard your own boat with this pontoon rental from Tarpon Springs. Choose from a half- or full-day rental and set your own pace to explore the Florida coast. Pontoons can fit up to eight passengers, great for smaller get-togethers, and come equipped with coolers, an entertainment center, and a 12-volt power receptacle for your comfort.

Bring your favorite food beverages and enjoy the Gulf breeze while on the lookout for our Dolphins and manatees that love to welcome our guests. Your Captain will intrigue you with the history of our local area and his many stories of travel making you feel like an old friend....