Top Clearwater Tours, Sightseeing & Cruises

Our Evening Sunset Cruise is a 2 hour cruise of the Intracoastal Waterway, Clearwater Pass, and into the Gulf of Mexico (weather permitting). Your crew will point out interesting Gulf Coast sights, including the ICW's abundant dolphins! Our boat is a 46-foot long, 2 deck vessel certified by the Coast Guard to carry 49 passengers. We limit cruises to 36 people to ensure a comfortable and spacious cruise for all guests. A complimentary champagne toast is included for all guests age 21 and over. Beer, wine, hard seltzers, and soft drinks are available for purchase while on board. Please note - the boat departs at the listed time. Please arrive 15 minutes prior to facilitate check-in and boarding.

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.

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.

Spice up any Florida vacation aboard an exciting dance cruise on Clearwater Bay. Beginning in Clearwater Beach, relax, enjoy the beautiful scenery, and listen to live music on board the elegant StarLite Majesty yacht. Choose from the open-air observation deck or select the air-conditioned dining cabin inside. Either way, the view is incredible and the party is just getting started. Upgrade to include a 3-course lunch; there are six delicious meals to choose from, plus a variety of beverages available to purchase.

We offer a 3 1/2 hour trip starting between 9 AM and 11AM. Pickup is available at two locations, Clearwater Beach recreation center docks or Bellair Boat Launch docks. Both locations usually have ample parking available. This is a private charter, meaning your group will be the only passengers. Children are welcome, but for their safety small children will be required to wear life jackets. You may spend up to two hours exploring the beaches or islands; the rest of the time will be spent cruising. If you prefer all the time can be spent cruising and sight-seeing. Activities include snorkeling, dolphin watching, shelling, swimming, sight seeing, island exploration, bird watching and much more. If desired, we stop at Caladesi or Honeymoon Island and other nearby remote beach areas for picnics and other activities.

Taking off from Clearwater Airpark just minutes from the beach this flight will give you a birds-eye view of some of the top-ten most popular beaches in the world. The sand is a beautiful white, the marine life is plentiful, the barrier islands are pristine and the thrill of flying over it all is something you will never forget. Don't forget your camera.

We will embark on an 8 mile loop of the Clearwater Beach & Boardwalk area. We will go over the Causeway Bridge, go to the old fishing pier and what is considered "Old Clearwater," possibly see some dolphins and take in the panoramic views of CWB then head back to our starting point as we cross Pier 60.

Enjoy a refreshing Ice cream on-board our brand new 50 passenger catamaran. This tour is a great way of exploring the beautiful Clearwater Beach for the whole family. The boat is fully shaded to protect customers from the sun.

Departing from Clearwater Airpark just minutes from the beach, what a view from above! Iconic Pier 60 features a boardwalk, fisherman and boats galore, a marina with yachts, a park, and beautiful beaches. The sand is a beautiful white, the marine life is plentiful and you cannot beat the thrill of flying over it all.

Departing from Clearwater Airpark just minutes from the beach, head north towards the famous Tarpon Springs Sponge Docks. Fly by Pinellas County’s largest lake on the way to the Anclote River. Continue south along the coast over the beautiful waterfront mansions of Palm Harbor and Crystal Beach then glide over Clearwater Beach, Honeymoon Island, and Caladesi Island like you never have before! The sand is a beautiful white, the marine life is plentiful, the barrier islands are pristine and the thrill of flying over it all is something you will never forget. Don't forget your camera.

Our one-of-a-kind floating Tiki Bars are the newest and best way to experience the water. These tiki boats are a lot of fun and should be on everyone’s bucket list! Take in views of Clearwater Beach from the Gulf of Mexico and admire the many stunning homes and boats which line the harbor, all while sipping your favorite drink. Our tours offer up-close encounters with dolphins, manatees and other wildlife. Bring your own beverages of choice, food or snack. We provide USCG certified captains, coolers with ice, and Bluetooth radio to play your favorite tunes. Why pay for over priced drinks at a land bar, when you can bring your own drinks on a floating Tiki Bar!

50 foot Shark themed vessel. The only shark that dolphins love. Covered vessel with sun area. Padded seats and restroom.

Adults and children of all ages love the Little Toot because of our “tug boat” shape and power, we create a huge wake that Dolphins love to jump and play in. The Little Toot offers closer dolphin sightings because the boat is lower to the waters edge. We provide a narrated sightseeing tour of Clearwater Harbor and the Gulf of Mexico.

Take to the skies on a helicopter tour of Clearwater Beach and its surroundings. You'll have bird's-eye views of the white sands, turquoise water, Pier 60, golf courses, and the barrier islands. This is a great way to escape the crowds and gain another perspective on this popular vacation destination. Booking in advance means you won't risk a sold-out tour.

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 10 passengers. Sit back and relax on the very comfortable, 27 foot double-decker Platinum 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, bachelor(ette) parties, marriage proposals, romantic getaways, reunions, spreading ashes, or any other reason!

Established in 1999, Encounters With Dolphins has been safely providing guests the opportunity to view dolphins, learn about Clearwater and enjoy the sand and sun on Compass Island and maybe even take a dip on the island! We are a veteran owned and operated small business founded on the principal of wanting our guests to have the same experiences we would want to have on our vacation! All of us work tirelessly to ensure that all of our customers have an enjoyable, relaxing time with us!

Explore delightful Dunedin on a bicycle tour that will amaze the senses. Experience the history of our quaint little Gulf Coast town! Your tour guide will escort you through small town Dunedin, while narrating the history of our community. Visit one of a kind locations that are off the beaten path (literally)! Enjoy historical landmarks, blooming fauna, and breathtaking views, all while riding a bike on the Pinellas Trail and side streets of Dunedin. You may encounter some of the local wildlife...like peacocks in the park or spot a dolphin playing in the gulf waters. Each tour is fun, unique and different….always something new! Come join us for a leisurely, 3-hour, 6-7 mile tour around our great town! (Don’t worry, it’s flat!)

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!

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.

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 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, bachelor(ette) parties, marriage proposals, romantic getaways, reunions, spreading ashes, or any other reason!

THE PRICE IS FOR A 4-HOUR BOAT CHARTER AND INCLUDES UP TO 6 PEOPLE IN YOUR GROUP. A Boat Day offers private, customized half-day and full-day boat charters for small groups of 1-6 passengers. Sit back and relax on the very comfortable, 24 foot Hurricane Deckboat 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!

A great way to end the day. Enjoy a relaxing ride from Cove Cay Marina to Whiskey's Joe Bar and Grill were food and drinks are available for purchase and then enjoy your ride home while the sun is setting. Food and Beverages are not included but guest may bring on board their own food and beverages.