Top Clearwater Walking Tours

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.

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.

Spice up any Florida vacation with a cruise on Tampa Bay. Beginning in Clearwater, enjoy a beautiful sunset (depending upon the time of year) and listen to live music on board the elegant 'StarLite Majesty' yacht. Choose from one of the open-air observation decks or the climate-controlled dining cabin inside. For dinner (at own expense), choose from several delicious gourmet meal entrees along with salad, dessert, and coffee or tea. Then dance the night away or take a romantic stroll along the deck.

The Gulf of Mexico is known for wild dolphin sightings and this tour from Clearwater Beach helps you discover the pods. Climb aboard the Little Toot, a tugboat-style boat, that creates a big wake that dolphins like to play in. While you’re out on the water, enjoy lively commentary about the dolphins and the surrounding area.

Dolphin encounters are quite common in the Gulf of Mexico, but this boat tour lets you get a closer look at them. Sail out towards Compass Island and keep your eyes peeled for the playful creatures while your captain provides commentary about your surroundings. Then, once you reach the island, jump in the water to search for marine life, collect shells, or simply enjoy the water.

The original Tarpon Springs ghost tour. Led by screenwriter and local guide Ace Chapman. Real history. Real true crime. No theatrics. This walking tour covers the story of Marshal Ruben Jones — described by a former Mayor as "the toughest, meanest, killingest man" in Tarpon Springs. Elected Marshal for 12 straight terms. Shot a man in the back at Spring Bayou. Tried and acquitted. Found with 80+ bullet wounds on a hunting trip. Case unsolved. His gold badge is at the Tarpon Springs Police Department. Guests use dowsing rods at the historic Train Depot and a spirit box during select moments. Many have heard their own names. There is also Mary — a documented spirit who responds to Ace on demand. Her story is shared on the tour. No costumes, no actors, no fake equipment. The original Tarpon Springs ghost tour. Running since 2023. Badge of Excellence on Viator.

Take a daytime or evening cruise around Clearwater, Florida aboard the Calypso Queen. A lunch or dinner buffet, as well as an open bar featuring rum punch, wine, and beer, is included. A full bar and dessert available for purchase. The evening cruise includes a DJ and dancing.

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.

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 is known for its beaches and sunsets, but there’s a different tale to this Gulf Coast city when the stars come out. Join this spine-tingling small-group walking tour through Clearwater’s Safety Harbor, covering documented true crime, local legends, and paranormal activity at historic landmarks—no costumes or theatrics. Includes entry to the Safety Harbor Resort and Spa lobby, and guests participate in hunting for ghosts using paranormal equipment.

Jimbos Jumbo Food Tours isn’t just about eating—it’s an interactive, high-energy adventure that blends amazing street food, quirky local history, and lively competition. Our exclusive walking trivia game keeps guests engaged, with a mystery prize awaiting the winning team! With a mix of hidden gems, bold flavors, and non-stop laughs, we create an unforgettable experience that’s as entertaining as it is delicious! Plus, only on our tour will you learn the Secret Chant, a magical celebration of food and fun. So come hungry and munch your way through Safety Harbor’s tastiest spots while competing for foodie glory—only the sharpest minds and hungriest bellies can win! Big bites, big laughs, and unforgettable fun await! An unforgettable experience that’s as entertaining as it is delicious!

Learn all about the fishing and sponging industry in Tarpon Springs with this guided tour along the Florida city's Sponge Docks. You'll also learn all about the Greek-American community here in the city and even get to sip on thick, dark "mud coffee" while snacking on traditional Greek pastries.

Discover the best of Clearwater Beach and cover a lot of ground on a guided Segway tour. Join your guide and small group for a roll down the boardwalk, across Causeway Bridge, Pier 60, and more. Enjoy commentary about the area from your guide, keep your eyes peeled for dolphins in the distance, and enjoy panoramic views while you ride.

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.

You'll learn abot the history of Tarpons early days and the Victorian influences, which still graces Spring Bayou. You'll arrive at the historic train depot and learn aabout the lives and lifestyles of he residents of the "Venice of the South"