Top Clearwater Tours, Sightseeing & Cruises - page 2

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.

Paddle around Clearwater Beach with the help of a guide to help you spot some amazing local wildlife as you soak up the sights of the sea. Keep your eyes peeled for dolphins and manatees from your transparent kayak while your CPR and first-aid-trained tour leader helps you make memories to last a lifetime.

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.

Discover the beautiful scenery of Florida’s Gulf Coast with ease on this half-day private eco boat tour from Holiday. Go island hopping, with stops at Caladesi Island, Honeymoon Island, and Anciote Key Preserve state parks, where you can relax on the beach, play in the water, and look for shells, wildlife, and historical sites.

Freestyle jet skiing is the ultimate adrenaline rush, combining skill, speed, and creativity on the water. Imagine powering across the waves, launching into the air, and performing jaw-dropping flips, spins, and aerial tricks with total control and style. It’s all about testing your limits and experiencing the thrill of high-energy water action like never before. Whether you’re an experienced rider perfecting advanced maneuvers or a beginner eager to try something exciting, our premium freestyle jet skis are built to deliver exceptional performance, balance, and responsiveness. Designed specifically for extreme riding, they provide the power and stability needed to help you ride confidently and make every session unforgettable. Get ready to elevate your adventure and experience freestyle jet skiing at its finest!

Freestyle jet skiing delivers an unmatched rush for anyone eager to take water sports to the next level. Feel the excitement as you ride across the waves, launch into the air, and perform impressive flips, spins, and daring tricks with confidence, balance, and style. Every ride is an opportunity to challenge yourself, improve your skills, and experience the thrill of complete freedom on the water. From experienced freestyle athletes to first-time riders seeking an unforgettable adventure, our premium high-performance jet skis are engineered to meet the demands of extreme riding. Built for power, agility, and control, they provide the perfect combination of speed and stability to help you maximize every jump, maneuver, and landing. No matter your skill level, you’ll enjoy an adrenaline-filled experience designed to create lasting memories and take your freestyle riding to new heights.

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!

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh less than 275 pounds - IMPORTANT- plan to arrive 45 minutes before departure time for mandatory check in to collect your boarding passes. -Our USCG credentialed Captain & Crew will welcome you on board like an old friend and treat you to a relaxed sailing excursion. -Expect a 5 Star "True Sailing Experience" on our 52' custom steel Schooner sailing vessel. -Our motto is "We SAIL and We SAIL Well"!

Freestyle jet skiing delivers the ultimate combination of excitement, performance, and adventure on the water. Feel the rush as you cut through rolling waves, launch into the air, and pull off incredible flips, spins, and aerial tricks with skill and precision. Every session is packed with energy, speed, and nonstop action, creating an unforgettable experience for adrenaline lovers and water sports enthusiasts seeking the next level of thrill. Whether you’re an experienced rider refining advanced freestyle techniques or a beginner ready to push your limits, our high-performance jet skis are designed to handle the intensity of extreme riding. Engineered for exceptional power, balance, and maneuverability, they offer superior control and responsiveness in every move. From sharp turns to smooth landings, our jet skis help you ride confidently while maximizing every moment of excitement on the water.

Take a tour of one of Florida's handful of wineries on this excursion in Clearwater. Follow your guide through a tour of the winery whilst you learn about wine production methods. Then, enjoy a tasting of three onsite-produced wines. Nibble charcuterie as you go to keep your palette neutral so you are able to pick up on the unique flavor profiles.

Experience Clearwater Beach like never before on a guided clear kayak tour! Paddle through the sparkling turquoise waters and explore the scenic waterways in a completely transparent kayak, offering unparalleled views of the underwater world. This is a family-friendly adventure is perfect for all skill levels. Keep an eye out for dolphins, manatees, and other fascinating marine life as you journey from the dock area to a beautiful sandbar. Our knowledgeable guides will share intriguing stories about the local ecology, wildlife, and the history of Clearwater Beach, making this an unforgettable experience.

Experience the best of Florida’s coast aboard your own private boat. Charter this spacious boat for a half 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.

Freestyle jet skiing is the perfect combination of adrenaline, adventure, and nonstop excitement on the water. It gives riders the opportunity to push the limits of performance while experiencing the unmatched thrill of speed, agility, and freedom. Picture yourself carving through open water, launching off rolling waves, soaring through the air, and landing exciting spins, flips, and freestyle tricks with precision and confidence. Every ride offers a rush unlike any other, blending skill, balance, and power into one unforgettable experience. Whether you’re a seasoned rider looking to perfect your next trick or a first-time adventurer ready to challenge yourself, our high-performance jet skis are designed to deliver maximum excitement and control. Engineered for freestyle riding, they provide outstanding handling, stability, and responsiveness, allowing you to ride harder, push further, and fully enjoy every second on the water.

Enjoy a day of adventure exploring the waters of Clearwater Beach. Step away from the crowds on Clearwater beach and island hop, dolphin watching, snorkel, shelling, and enjoy the nature our waters have to offer. Relax and enjoy the sunshine on our 27 foot pontoon boat with incredible stereo system and comfortable seating. Hope to see you soon!

Skip the crowded pontoon boats and step aboard a private 6-passenger Sea Ray designed for a more personal and unforgettable day on the water. Smaller, faster, and far more intimate than large tour boats, this experience lets you explore farther and enjoy the water the way it was meant to be. Relax, swim, and play with all the fun water toys included—from paddleboards and snorkel gear to the popular Bote Hangout floating dock, plus oversized pool noodles for ultimate lounging. Whether you're looking for a fun day with friends, a family adventure, or a laid-back cruise, this experience delivers comfort, flexibility, and a truly local vibe. The boat also includes an onboard restroom for added convenience so you can stay out on the water longer. And remember—it’s not just about the boat, it’s about the captain. Your experienced captain knows the best spots to explore, relax, and make the most of your time on the water.

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.

Soak up some of Florida’s most spectacular beachy scenery, and enjoy a relaxing excursion out on the water, on this private boat charter. 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.

Freestyle jet skiing is the ultimate thrill for riders who want to push the limits on the water. Imagine carving through waves, launching into the air, and pulling off breathtaking flips, spins, and high-energy tricks with total control and style. It’s an adrenaline-packed experience that combines speed, skill, and freedom like no other water sport. Whether you’re an experienced freestyle rider or a beginner ready to challenge yourself, our top-performance jet skis are built to deliver power, balance, and precision for every ride. Designed specifically for freestyle action, they provide the stability and responsiveness needed to maximize every jump, turn, and maneuver. Get ready to elevate your adventure, master new tricks, and experience the excitement of freestyle jet skiing at its best.

Explore the waters of Clearwater on this island hopping and dolphin watching cruise. Travel by motor boat through the bay, with time to stop at a shallow sandbar for swimming and relaxation. The BYOB format and onboard music create an upbeat social setting, while the guided route offers a convenient way to enjoy Clearwater Beach from the water.

Explore beautiful Tarpon Springs with this hassle-free tandem kayak tour, where your guide takes care of all your gear and navigation, so you can just enjoy the experience. Spot wildlife with your guide’s help, who makes sure you don’t miss anything. Also stop by Tarpon Springs’s Historic Sponge Docks, and make sure to bring some home for useful souvenirs.

Take our luxury kayaks to a nearby spoiler island to play and explore! Our tour is not your typical gimmicky trip on a kayak! We want you to experience the island and what better way to get there than a 35-minute scenic paddle (one way/60-minute total) to it! Our kayaks are the most stable kayak in the industry. On our way we try to spot local wildlife (not guaranteed). When we get to the island go explore while jamming to your favorite tunes, search for shells, play some beach games, replenish and enjoy island time like us locals do!

* PRICE IS PER TANDEM KAYAK FOR 2 PEOPLE! * Experience the best kayaking adventure in Clearwater Beach, FL! Our 2 1/2-hour guided kayak tour takes you from North Clearwater Beach to a picturesque spoiler island in the heart of the intracoastal waterway. Paddle in comfort with our top-rated kayaks, specifically designed for smooth and stable navigation in the calm waters of the area. You will not flip over in our kayaks. During your journey, you’ll pass by stunning waterfront homes, lush landscapes, and encounter local wildlife, offering you a unique perspective of Clearwater's natural beauty. Once we reach the spoiler island, you’ll have an hour to relax, swim, play beach games, or explore the island at your leisure. We provide everything you need for an unforgettable adventure, including towels, a Bluetooth speaker for your favorite tunes, beach games, and a cooler stocked with refreshing water and snacks. Book your Clearwater Beach tour today for an unforgettable experience!

Take to the water and leave the crowds behind on this private, half-day boat tour led by a captain from Florida’s Clearwater Beach. Explore the coastline, look out for dolphins, and take a dip in the water before cooling off with ice cooler and bottled water included. Enjoy the flexibility to customize your itinerary with island hopping, stops at beach bars, sunbathing time, or more – it’s all up to you.

Embark on a sky-high adventure that will show you Clearwater from a whole new perspective. You’ll enjoy an unforgettable private helicopter ride with a professional crew that ensures your safety. Soar across Clearwater Beach’s sparkling blue water and white powder sand, enjoy a bird’s eye view of the famous Pier 60 fishing pier, and sweep above Florida’s first golf course at the scenic Bellair Country Club.