Best Clearwater Walking Tours 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 $ 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 $ 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 $ 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 $ 124.00

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 $ 40.00

Tarpon Springs may be known for its sponge docks and rich Greek heritage, but after dark, another side of the city comes alive. Join Ace Chapman, a screenwriter and longtime local guide, on the original and longest-running ghost tour in Tarpon Springs. This guided nighttime walking tour explores the haunted streets of downtown and the stories connected to historic landmarks such as the Train Depot, the Cheney House, and the Meres Building — all viewed from the outside as you uncover the city’s darker past. Ace’s tours are known for their authenticity. There are no made-up stories and no theatrics, just well-researched history, local insight, and reported paranormal activity shared with honesty and respect.

Clearwater , Florida

From $ 129.00

This isn’t a cookie-cutter food tour — its begins on the highest roof top bar (10th Floor) on Clearwater Beach, with a full-on bride tribe experience. Guests enjoy an all inclusive event with food and alcoholic drinks, a hilarious Bachelorette Trivia Challenge (complete with a secret prize), and even learn our famous Pre-Marital Celebration Chant that turns heads wherever we go! Our Bachelorette Mimosas, Munchies & Fun Food Tour is Clearwater Beach’s ultimate pre-wedding party on foot — where every sip, bite, and life time memories are created. - Explore Clearwater Beach's top beach food & drink spots with an enthusiastic guide. - Engage in a hilarious marriage trivia with a surprise gift for the winning team. - Customizable to your theme! - ADA-friendly tour.

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.

Clearwater , Florida

From $ 259.95

Looking to make unforgettable beach memories this March? Available all month long, our St. Patrick’s Day beach photoshoot is perfect for couples, friends, families, and solo travelers who want stunning photos with expert posing guidance. This fun seasonal photoshoot is perfect for anyone wanting festive beach portraits with a St. Patrick’s Day feel, without needing to book on St. Patrick’s Day itself. In just 1 fun-filled hour, we will guide you through easy, flattering poses. No experience needed. Whether you're celebrating St. Patty’s Day, a spring getaway, or just want an excuse to throw on your green, we’ve got you. After your session, your photographer will deliver your favorite 8 edited digital images plus 1 FREE, with the option to purchase more. No pressure. No obligation. Just stunning memories with a festive St. Patrick’s touch. If you would like us to travel to your location for your session, please include that request in the Notes section when booking.