Best Walking Tours in Clearwater 2025

Clearwater , Florida

From $ 25.00

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 offer over 35 different wines, made right here on site and we have a nice selection of local craft beers, cider and spiked seltzers, mostly local, as well as charcuterie. All of our wines are hand-crafted, right here at our veteran and family owned & operated winery.   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 $ 40.00

Step into the haunted history of Safety Harbor, Florida, on this top-rated Ghost and Haunted History Tour. Led by experienced paranormal investigator Cynthia Dominick, this walking tour takes you through the city’s most spirited sites—including the historic St. James Hotel, Safety Harbor Resort and Spa, and the elusive Hotel Frances. You’ll hear chilling ghost stories rooted in real local history, explore dark legends rarely told, and use authentic ghost-hunting equipment like spirit boxes and EMF detectors as you search for signs from the beyond. You may even encounter Cynthia’s longtime spirit companion, Mike—who’s known to make his presence known. This immersive experience is perfect for ghost hunters, history buffs, and anyone looking for a spooky night out in the Tampa Bay area. Every tour is different, depending on which spirits are ready to talk.

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 $ 145.00

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 with your choice of local craft beer, wine, or a house-made margarita.

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 $ 122.50

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 $ 40.00

Discover the haunted secrets of downtown Tarpon Springs on this spine-tingling Ghost and Haunted History Tour. Led by expert guide and paranormal investigator Ace Chapman, this tour takes you deep into the eerie past of one of Florida’s most historic cities. Explore haunted landmarks like the Tarpon Springs Train Depot, the Meres Building, the Cheney House, and the infamous Louise’s Saloon. Hear chilling true stories of lingering spirits—like Anna, Walter, and Charlotte—who are known to follow Ace through the shadows. Along the way, you’ll use real ghost-hunting equipment, including EMF detectors and spirit boxes, for a hands-on paranormal experience you won’t forget. Whether you're a believer or a skeptic, this tour is perfect for ghost hunters, history lovers, and anyone looking for a spooky and unforgettable night in Tarpon Springs.

Clearwater , Florida

From $ 165.00

The food tour that'll tantalize your taste buds with the rich greek foods that are found on the Aegean Islands. We'll talk about the history of Tarpon's early days and the Greek, Bahamian and Victorian influence. Take a walk through the 120 plus acres of the Sponge Dock District in Tarpon Springs, Florida.