Top Clearwater Cultural Tours

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.

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.

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.

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.

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.

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.

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"

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 Award for Best Tour, Silent Slayer has built its reputation on real experiences, not theatrical ones. This 90-minute walking tour covers documented history and paranormal activity downtown, including a hanging tree, a devastating fire, and a bank robbery, with stops at the historic Safety Harbor Resort and Spa lobby. The tour begins near City Hall, where since 2021 Silent Slayer has documented a firetruck phenomenon with no explanation. Guests finish with a ghost hunting sampler at the Elf Tree and a stop at the ancient Baranoff Oak. No costumes. No actors. No scripted jump scares.