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 cr…
★★★★★★★★★★4.7(104)Rated 4.7 out of 5 from 104 reviews30 minFree cancellation
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…
★★★★★★★★★★4.9(81)Rated 4.9 out of 5 from 81 reviews30 minFree cancellation
Clearwater's original clear kayak tour · 2.5 hours · free cancellation 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 anythin…
★★★★★★★★★★4.4(112)Rated 4.4 out of 5 from 112 reviews2 h 30 minFree cancellation
Embark on an unforgettable adventure with ParrotDise Express Boat Tours, offering premier Dolphin Excursions and captivating Sunset Tours in Clearwater and Dunedin. Cruise aboard the 47-foot ParrotDise Express, specially designed for optimal dolphin sightings, as you navigate stunning coastal waters. Experience wild dolphins up close while enjoying breathtaking views of Clearwater Beach and nearb…
★★★★★★★★★★4.8(68)Rated 4.8 out of 5 from 68 reviews2 h 30 minFree cancellation
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 s…
★★★★★★★★★★4.9(57)Rated 4.9 out of 5 from 57 reviews3 hFree cancellation
2026 Besties Award-winning original Safety Harbor ghost tour, running since 2021. Led by certified guide Cynthia Dominick. Real history. No theatrics. Safety Harbor is a small coastal town on Tampa Bay. After dark, it tells a different story. This is Safety Harbor's only ghost tour and the longest running — founded in 2021 by Cynthia Dominick. With a 4.9-star Google rating and the 2026 Besties Aw…
★★★★★★★★★★4.8(62)Rated 4.8 out of 5 from 62 reviews1 h 30 minFree cancellation
Discover Clearwater the local way on this 3-hour private boat tour aboard Salt Therapy with Captain Clearwater. Ideal for couples, families, or small groups, this mid-length adventure lets you see dolphins, visit sandbars, and relax along Florida’s Gulf Coast without rushing the day. Bring your favorite drinks, cue up the Bluetooth, and explore calm backwaters and island coves locals love most. W…
★★★★★★★★★★5.0(43)Rated 5.0 out of 5 from 43 reviews3 hFree cancellation
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!
★★★★★★★★★★4.6(55)Rated 4.6 out of 5 from 55 reviews1 h 30 minFree cancellation
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. Professional…
★★★★★★★★★★4.9(41)Rated 4.9 out of 5 from 41 reviews1 hFree cancellation
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 pa…
★★★★★★★★★★4.4(65)Rated 4.4 out of 5 from 65 reviews1 h 15 minFree cancellation
Escape the crowded group tours and experience Clearwater from the water on a more personal island adventure. Paddle across the beautiful Intracoastal Waterway to a secluded spoil island, where you’ll have time to explore, search for shells, play beach games, relax and enjoy your favorite music. Along the way, keep an eye out for dolphins, manatees and other local wildlife that frequently call the…
★★★★★★★★★★5.0(31)Rated 5.0 out of 5 from 31 reviews2 h 30 minFree cancellation
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…
★★★★★★★★★★5.0(28)Rated 5.0 out of 5 from 28 reviews4 hFree cancellation
Experience Clearwater from a new perspective as you paddle across bright turquoise water in a completely see-through kayak. This tour brings you closer to wildlife encounters that feel authentic. Dolphins often cruise through the harbor, rays move quietly along the shallow flats, and pelicans and herons perch along the water's edge. With a marine wildlife expert leading the way, you'll learn fun…
★★★★★★★★★★5.0(27)Rated 5.0 out of 5 from 27 reviews2 hFree cancellation
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 sa…
★★★★★★★★★★4.8(29)Rated 4.8 out of 5 from 29 reviews2 h 30 minFree cancellation
Experience one of the top-rated Clearwater Beach pontoon tours with private 2-hour and 4-hour options for up to 6 guests. Choose our 2-hour evening sunset cruise for a relaxing ride along the coast as you watch the sun set over the Gulf. Looking for more adventure? The 4-hour tour gives you time to explore local favorites like Caladesi Island, Honeymoon Island and Three Rooker, with opportunities…
★★★★★★★★★★5.0(24)Rated 5.0 out of 5 from 24 reviews4 hFree cancellation
Discover fascinating history, fun facts, and local favorites with our expert tour guides and historians as you explore the charming Main Street community of Dunedin along the Intracoastal Waterway. Experience the town’s vibrant vibe and incredible cuisine while enjoying delicious food and handcrafted drinks. The tour kicks off at Lucky Lobster, where you'll savor their famous lobster pizza paired…
★★★★★★★★★★4.8(28)Rated 4.8 out of 5 from 28 reviews3 hFree cancellation
Explore the vibrant heart of Clearwater in style aboard our spacious paddle pub boat! Set sail through the beautiful bay, passing luxurious yachts and picturesque mansions that line the shoreline, with a USCG-certified captain at the helm and a good chance of spotting dolphins along the way. Perfect for couples and medium-sized groups looking for a lovely day out, this 2-hour scenic cruise combin…
★★★★★★★★★★4.5(29)Rated 4.5 out of 5 from 29 reviews2 hFree cancellation
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…
★★★★★★★★★★5.0(18)Rated 5.0 out of 5 from 18 reviews4 hFree cancellation
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 a…
★★★★★★★★★★4.3(27)Rated 4.3 out of 5 from 27 reviews3 hFree cancellation
2026 Besties Award-winning original Tarpon Springs ghost tour. So good it was copied. Led by Ace Chapman — and long story short, it never is. Now in its fourth year, this is the original Tarpon Springs ghost tour, led by screenwriter and longtime local guide Ace Chapman. The history is real, researched, and specific — never borrowed, embellished, or sold as a paid upgrade. The tour covers downtow…
★★★★★★★★★★4.7(21)Rated 4.7 out of 5 from 21 reviews1 h 30 minFree cancellation
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 i…
★★★★★★★★★★5.0(15)Rated 5.0 out of 5 from 15 reviews4 hFree cancellation
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 Clearwa…
★★★★★★★★★★4.6(18)Rated 4.6 out of 5 from 18 reviews2 hFree cancellation
Explore Florida's Gulf Coast on a private inshore fishing charter from Holiday through the waters surrounding Anclote Key and nearby backcountry. This diverse coastal fishery combines shallow flats, protected waterways, barrier islands, and natural shorelines for a scenic day on the water. Depending on the season and conditions, target snook, redfish, spotted seatrout, tarpon, and other inshore s…
★★★★★★★★★★5.0(12)Rated 5.0 out of 5 from 12 reviews6 hFree cancellation
* PRICE IS PER TANDEM KAYAK FOR 2 PEOPLE! * Skip the crowded group tours and experience Clearwater from the water at your own pace. This 2.5-hour private guided kayak adventure is reserved exclusively for you and your group. We’ll paddle from North Clearwater Beach through the calm Intracoastal Waterway, passing beautiful waterfront homes, tropical scenery and local wildlife on our way to a seclu…
★★★★★★★★★★5.0(12)Rated 5.0 out of 5 from 12 reviews2 h 30 minFree cancellation
