Top Clearwater How to Get Around in 2026

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. A full bar and dessert available for purchase. The evening cruise includes a DJ and dancing.

Hop aboard Clearwater’s ultimate dolphin-spotting boat tour. This high-speed adventure lets you cover more of the Gulf—and increases your chances of seeing dolphins up close as they play and surf in the wake. Cruise past celebrity homes and coastal landmarks on this powerful 73-foot vessel captained by seasoned pros.

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.

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 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.

The Starlite Infinity offers more than a standard sightseeing cruise—it’s a full evening experience on the water. Guests can enjoy scenic views along Clearwater Beach and the Intracoastal Waterway, relax in comfortable indoor seating, step outside to open-air deck spaces, sip cocktails, enjoy DJ entertainment, and dance as the night continues. What makes this cruise unique is the combination of atmosphere, entertainment, and flexibility. Your ticket includes the cruise, reserved seating, music, and dancing. Freshly prepared entrees and beverages are available for purchase on board. It’s an ideal choice for date nights, celebrations, visitors, locals, and groups looking for a memorable night out on the water. If you are joining another party or reservation, please note the reservation name in the "Special Requirements" section on the booking page.

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.

Wildlife cruises are always a gamble when it comes to spotting animals—but during this boat ride along the emerald-green waters of Clearwater Beach, dolphin sightings are guaranteed. Relax onboard the comfortable, restroom-equipped boat as you take in the Gulf Coast’s picturesque scenery, listening to insights about the region’s history and natural heritage from guides along the way.

Explore the Anclote River on a guided kayak eco tour with a small group. Follow your wildlife expert guide as you paddle through the mangroves, keeping an eye out for wildlife such as dolphins, manatees, and bald eagles. Learn about the unique ecosystem and stop at the historic Tarpon Springs Sponge Docks along the way.

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.

Leave our launch with your guide before the sun has set. Navigate through the mangroves and the shallows as you witness the surrounding ecosystems transition from day to night, a time when the wildlife is most active. You will arrive at a bridge and wait as you hear the bats under the bridge getting louder and louder. Then watch as they depart their home, sometimes a handful sometimes over a hundred, depending on weather conditions. Paddle back as the night sky gets darker and your guide will talk you through some of the visible constellations.

Climb aboard a schooner for an afternoon of sailing in Clearwater Beach with this tour. Enjoy sea breezes and admire views you wouldn't get if you stayed on shore 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. Note that hard soled shoes are not allowed onboard for safety.

Spot dolphins and other marine life on this playful boat ride aboard a one-of-a-kind 50-foot shark-themed vessel. This specialized boat creates a mega wake that attracts dolphins, and the boat’s shark design is fun for all ages. While on board, you’ll hear interesting Clearwater Beach facts and stories, as you spot attractions and famous homes on land and dolphins in the water.

Clearwater has some of the best voted beaches in the United States and this exciting tiki tour is a great way to experience the Gulf waters. Hop aboard the only U.S. Coast Guard certified tiki boat in Clearwater Beach for a fun day under the sun. Perfect for celebrations, this cruise can hold over a dozen people for a party. An open bar with beers and cocktails is included.

Many beaches, sandbars, islands, and backwater coves along Florida’s Gulf Coast are only reachable by boat—but some operators try to pack in as many travelers as possible, making a cruise feel more like a spin in a cramped elevator. Treat yourself to a deluxe experience on this private, chartered boat ride, whether that's swimming, picnicking, spotting bottlenose dolphins, or simply relaxing on deck to your own music—Bluetooth included.

Embark on a scenic journey to find bottlenose dolphins on this dolphin-watching cruise from Clearwater in Florida. Enjoy the incredible views along the Intracoastal Waterway, passing celebrity mansions while listening to the captain’s commentary. Snacks and beverages are available for purchase on board. Dolphin sightings are guaranteed on this exciting tour—in the unlikely event you don’t see them, you can take another cruise at another time for free.

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 Clearwater Beach like never before on your guided two-hour Dolphin Kayak and Island Excursion departing directly from Shephard’s Beach Resort. Paddle through calm Gulf waters as you search for wild dolphins, observe the natural beauty of Bird Island, and enjoy fascinating coastal history shared by local guides. Guests may also spot gentle manatees and sea turtles while enjoying Clearwater’s famous crystal-clear waters and shallow sandbars. Perfect for beginners, families, and adventure seekers looking for an unforgettable experience on the water.

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.

Whether you're a seasoned pro or a first-time rider looking to test your limits, our high-performance jet skis are specifically designed to handle the demands of freestyle riding, ensuring you get the most out of your experience! Freestyle jet skiing is the ultimate adrenaline rush, combining skill, speed, and creativity on the water. It’s all about testing your limits and experiencing the thrill of high-energy water action like never before.

Whether you're a seasoned pro or a first-time rider looking to test your limits, our high-performance jet skis are specifically designed to handle the demands of freestyle riding, ensuring you get the most out of your experience! Freestyle jet skiing is the ultimate adrenaline rush, combining skill, speed, and creativity on the water. It’s all about testing your limits and experiencing the thrill of high-energy water action like never before.

Set sail on a lively Tiki Getaway cruise along Clearwater Beach, where you can soak in the sun and enjoy the open air. This 1.5 to 2-hour tour features a spacious tiki boat with plenty of seating and a friendly crew eager to share fascinating stories about the local history and landmarks. Dolphin sightings are common, so keep your camera ready. Guests can bring their own beverages (no glass, please) and enjoy complimentary water and soda on board, making it a perfect outing for groups of friends or families looking for a casual, fun atmosphere. - 1.5 to 2-hour cruising experience along Clearwater Beach - BYOB cruise with one complimentary water or soda provided - Spacious tiki boat with ample seating and shade - Dolphin sightings are common; perfect for families and groups - Enjoy golden hour for a Clearwater Beach sunset - Restroom available on board

Spend an unforgettable half-day exploring Clearwater’s islands and calm Gulf waters aboard Salt Therapy with Captain Clearwater. This 4-hour private cruise is the perfect balance of adventure and relaxation—see dolphins, visit sandbars, swim, snorkel, or anchor up for a floating picnic. Bring your own drinks and tunes while your USCG-licensed captain shares local stories and secret spots known only to Clearwater regulars. With flexible pickup points and a laid-back pace, this is how locals spend their day off: sun on your face, salt in the air, and time on your side. All Captain Clearwater charters are private, customizable, and flexible based on weather and guest preference. Highlights • Half-day (4-hour) private charter aboard Salt Therapy • Explore sandbars & barrier-island beaches • Dolphin watching & swimming stops • Cooler, ice & bottled water included • Pickup in Clearwater, Belleair & IRB Chase the sun, drop the anchor, and let island time take over—“Boat Like a Local.”

You'll learn abot the history of Tarpons early days and the Victorian influences, which still graces Spring Bayou. You'll arrive at the historic train depot and learn aabout the lives and lifestyles of he residents of the "Venice of the South"