Top Clearwater Cruises & Sailing

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 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.

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.

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.

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.

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.

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.

Clearwater Fun Boat invites you to an ICE CREAM TOUR. A unique experience for the whole family. Come join us for a fun filled excursion to see and learn about beautiful Clearwater Beach, watch dolphins and relax while having a wonderful ice cream sundae. We offer daily Ice Cream Tours, Sunset Tours and Adult Only Booze Cruises.

Go in search of bottlenose dolphins on this dolphin cruise from Florida’s Clearwater Bay to the beautiful, emerald-green waters of the Gulf of Mexico. Enjoy $5.00 "You Call it" cocktails during this Happy Hour Dolphin Exploration Tour! Listen to great music as your Crew highlights interesting facts about the Gulf Coast and our Celebrity homes in the area. Dolphin sightings are guaranteed!

This is the only boat of its kind in the entire United States. We not only do tour of the Clearwater Beach area but we also can provide a one of a kind shelling adventure that is fun for all ages. Everyone can take home shark teeth and shells.

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.

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.

We offer private, customizable, scenic boat tours, sunset cruises, and island hopping. We are all about fun, family, and being on the water. Relax and let us show you how to avoid the crowds and beach like a local. See and explore Florida's beautiful beaches and waterways on a private boat with a licensed Captain. Serving Clearwater Beach, Dunedin, Palm Harbor, and Indian Rocks Beach. My vessel is a safe and comfortable Century 2200 Center Console with cushioned bow and stern seating. I always supply a USCG-approved Type 1 PFD for each occupant.

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!

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!

Enjoy a day of adventure exploring the barrier islands of Clearwater Beach. Get away from the crowds and see dolphins, island hop, snorkel, shell, and park on secluded islands away from all the crowded beaches. Play or relax on our 18ft. water mat and bring as many drinks and food as you want! We offer sunset tours as well! These tours are great for families, friends, bachelorette parties, bachelor parties, work parties, reunions, marriage proposals, birthdays, anniversaries, and you're want to get away for the days! These tours can be customized from 2-6 hours.

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!

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.

One of a kind 25' Pontoon Boat with Water Slide! Explore local waters and islands, visiting beaches that are only accessible by boat. See Historic Sponge Docks from the Anclote River and wildlife in their natural habitat during your private charter.