Clearwater, Florida Tours & Activities in 2026

Clearwater , Florida

From $ 25.00

Started in 2010, Aspirations Winery was named by Yelp and House Beautiful Magazine as the #1 winery in the State of Florida, and we are consistently ranked as one of the top things to do in Clearwater! Our relaxed atmosphere, along with friendly staff, make Aspirations Winery a must visit! We handcraft over 40 different CLEAN wines, made right here on site and we have a nice selection of local craft beers, cocktails, food & more! All of our CLEAN wines are hand-crafted, right here at our veteran and family owned & operated winery. We also have a beautiful private event space for your next special event or fundraiser. Although we specialize in making some of the tastiest award winning, fruit-infused wines around, we also produce your favorite dry reds, whites as well as some dessert wines. Round up your friends and book yours today and see why we are a top rated winery in Florida!

Clearwater , Florida

From $ 74.00

Take a 100% clear kayak-guided tour with us! Enjoy a one-of-a-kind experience where you can come and see Clear through Clearwater! We take great pride in offering amazing clear kayak adventures in the beautiful waters surrounding Clearwater Beach. As experienced Tour Guides, we've worked hard to make sure our tours are anything but run-of-the-mill. We regularly find Dolphins, Manatees, and many other types of wildlife. Our guides have been trained in CPR, first-aid, and ACA Kayak rescue so you can rest assured you’re guide has the training to have a safe and fun tour. At Sea Glass Kayaking, we would like to inform everyone that we operate on a reservation-only basis No walkup's are available. Please note that due to license requirements in the city of Clearwater, Guided rental customers at our 69 Bay Esplanade location are required to launch the kayaks themselves. Our team is available to offer instruction to ensure a successful launch. Please sea our website for more info.

Clearwater , Florida

From $ 33.96

If you are joining another party or reservation, please note the reservation name in the "Special Requirements" section on the booking page. Take a leisurely afternoon sightseeing cruise in Florida’s beautiful inland waters aboard a luxury yacht with optional luncheon service. Your captain will provide informative narration on the area’s history and points of interest. Head to the outer decks and look for dolphins and other wildlife, or relax in the climate-controlled luxury of the vessel’s interior.

Clearwater , Florida

From $ 69.00

Experience the beauty of Tarpon Springs like never before as you paddle through the scenic Anclote River in a completely clear kayak! While the water here has a natural tannin tint, our transparent kayaks still provide a unique way to view the fascinating ecosystem beneath you. This tour takes you through the heart of Florida’s famous sponge-diving town, where you’ll paddle past the historic Tarpon Springs Sponge Docks and explore the winding waterways of the Anclote River. The area is home to a variety of wildlife, including fish, birds, and the occasional dolphin sighting. While wildlife encounters can’t be guaranteed, each trip offers a chance to experience Florida’s natural beauty up close. This guided tour is a fun and relaxing way to explore one of Florida’s most charming coastal destinations. Whether you’re looking for a peaceful escape or a unique outdoor adventure, our clear kayaks provide an unforgettable experience.

Clearwater , Florida

From $ 54.00

Experience Anclote River and everything it has to offer. You'll be guided through the mangroves spotting wildlife along the way. Learning about the Eco Systems here in Florida and stopping by the Historic Sponge Docks.

Clearwater , Florida

From $ 40.00

Experience the longest-running ghost tour in Safety Harbor, where haunted history, true crime, and real paranormal activity come together after dark. Led by local resident and professional paranormal investigator Cynthia Dominick, this immersive 90-minute walking tour explores the stories that shaped downtown Safety Harbor. Guests hear chilling accounts connected to an infamous hanging tree, a devastating historic fire, a murder linked to a possible brothel, a destructive unnamed hurricane, a daring bank robbery, and the city’s funeral home past. Along the route, guests learn about reported ghost sightings at the St. James Hotel, investigate legends surrounding the haunted dog statue, and uncover why Safety Harbor’s healing waters and sacred Tocobaga grounds are believed to hold lingering energy.

Clearwater , Florida

From $ 40.77

If you are joining another party or reservation, please note the reservation name in the "Special Requirements" section on the booking page. Get your friends together for a little midday party aboard a sleek, yacht-style luxury vessel! Enjoy the scenery of Clearwater Bay as you cruise to the sounds of live entertainment!

Clearwater , Florida

From $ 34.95

Guaranteed Dolphin Siting! Set Sail for Adventure. Explore Clearwater Beach on an Unforgettable Dolphin, Island Swim & Sunset Cruises. Enjoy your Island Sandbar stop at One Tree Island, where you can enjoy the beautiful waters of Clearwater Beach. Welcome aboard the ultimate coastal adventure with Fins Up Clearwater! Dive into the crystal-clear waters of Clearwater Beach and let us whisk you away on a journey of discovery and delight. Embark on our exhilarating Sandbar Tours, where you can explore hidden treasures and pristine shores. Glide through the waves on our Dolphin Cruises, witnessing these majestic creatures in their natural habitat. Experience the breathtaking beauty of a Sunset Cruise as the sky paints a masterpiece. Let Fins Up Clearwater be your guide to unforgettable moments and endless wonder along Florida’s stunning coastline.

Clearwater , Florida

From $ 62.00

Sharkey's Glass Bottom LED illuminated Fish Feeding Night tours in our glass bottom kayaks is an amazing experience with our tour guides paddling in calm shallow waterways under the stars! Our tour guides will point out sea birds and various sea-life such as different fish species, shrimp, crabs, conch shells which will be well illuminated with our high powered underwater custom LED lights. We paddle along a nature preserve with mangrove shorelines and canals so we sometimes even see wild animals such as Racoons along the shoreline. We've also experienced manatees and dolphins on many of our tours. Definitely one of the most exciting things about our kayak tour is that we will feed fish at a certain point of our tour as well which is a blast for everyone! With very little to do at night this is an amazing rare experience under the stars that you'll never forget!

Clearwater , Florida

From $ 52.00

You'll Stroll the World Famous Sponge Docks and learn about the thriving fishing and sponging industry. Taste authentic Greek pastries and coffee in a Bakery that is almost to 100 years old. Walk where the first sponge divers stored there sponges. All tours can be customized and/or private!

Clearwater , Florida

From $ 104.00

We have experienced parasail captains with over 50 years combined and they are entertaining as well as informative about what to expect on your activity. We can take a few observers on the boat as well for a nominal fee and if you change your mind and want to go we can do that too!

Clearwater , Florida

From $ 119.00

The Fun Food Tour!—it’s a full-on Tiki-Tastic adventure! A ridiculously fun, high-energy, beach bites, bold Trivia & belly laughs, 3 HR walking food adventure through the heart of Clearwater Beach! - Food & Drink Experience 5 locally loved & hidden gems food tastings - Local Quirky History Learn fun local history without ever feeling like a history class. - Hilarious Trivia Challenge Guests are split into teams for a fun, interactive trivia contest woven seamlessly into the experience - Secret Prize Winning teams earns a secret prize. - The Magical Foodie Chant Our legendary foodie chant—a playful moment that bring smiles. - Complimentary Photo Package We capture the laughs, the competition, and the memories—so you can relive the experience & share it afterward! - Optional - Alcoholic Drink Package Come hungry, bring your A-game, and get ready for unforgettable memories!✨ The Fun Food Tour!!!

Clearwater , Florida

From $ 65.00

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!)

Clearwater , Florida

From $ 99.00

Looking to make beach memories? Our Express Photoshoot is perfect for couples, families, and solo travelers who want stunning photos with expert posing guidance in less time. In just 30 fun-filled minutes, your photographer will guide you through easy, flattering poses. No experience needed! Whether you're celebrating a milestone, marking your vacation, or just want beautiful sunset shots, we've got you. At the end of the session, your photographer will deliver your favorite 4 fully edited, digital images from the session, with the option to purchase more. No pressure. No obligation. Just stunning beach memories.

Clearwater , Florida

From $ 259.95

You’ve waited all year for this trip—make it count. Our photo sessions aren’t just pictures, they’re an experience: laughter in the golden light, sand between your toes, the kind of joy that sneaks up on you and stays forever. Whether it’s your chosen family, your wild-hearted kids, or your once-in-a-lifetime getaway, we’ll capture the spirit of it all—with heart, artistry, and soul. Professionally edited images delivered the same night. Fridge-worthy. Frame-worthy. Heart-worthy.

Clearwater , Florida

From $ 68.00

Experience a once in a lifetime opportunity of kayaking with Manatees. Start at our launch then paddle past the historic Sponge Docks, learning about the area's unique history. Then, enter the mangroves and learn all about their important role as part of Florida's coastal ecosystems. Float into the freshwater spring to join the Manatees in the warm water. Your guide will instruct you on how to safely navigate the water so you do not disturb these protected mammals. Then work your way back while the guide continues to point out wildlife along the way.