Top Clearwater Historical Tours

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.

The Gulf Coast town of Dunedin may be small but it’s full of history. Discover the best of Dunedin on a small-group bike tour and discover landmarks like Hammock Park, Kellogg Mansion, the Fenway Hotel, and more. Listen to the town’s history from your guide and keep your eyes peeled for local wildlife while riding along the trail.

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.

See the best of Dunedin in an afternoon with this guided bike ride. Pedal past green spaces, such as Hammock Park and its idyllic butterfly garden; see the TD Ballpark baseball field, and learn about the history of the Fenway Hotel, and the Kellogg Mansion. Traveling with a guide means there’s no need to worry about navigating, and there’s an opportunity to learn plenty of fun facts along the way.

Our local guides are experts for your bicycle tour experience! We showcase the local gems within Tarpon Springs sharing the history of the area and the cultural significance it has on today's society.

Embark on a scenic journey to find bottlenose dolphins on this dolphin-watching cruise near Clearwater in Florida. From Clearwater Bay to the turquoise waters of the Gulf of Mexico, enjoy the incredible views along the Intracoastal Waterway. See and hear about the celebrity mansions on the coast, and listen as the captain shares interesting facts about the natural wonders of the Gulf Coast region. Snacks and beverages are available for purchase on board. Dolphin sightings are guaranteed on this exciting tour.

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. The evening cruise includes a DJ and dancing.

Experience the best of Florida’s coast aboard your own private boat. Charter this spacious boat for a few hours or an entire day and tell the captain what you’d like to see. Then, sit back and relax while you sail on the Gulf of Mexico in search of pristine beaches or idyllic swim spots. Book this experience for a special occasion or just a casual boat day.

50-foot shark themed vessel. The only shark that dolphins love, producing a "MEGA" wake that dolphins love to jump and play in. Covered vessel with sun area. Padded seats and restroom.

Watch as day turns into night off the coast of Florida on this sunset cruise from Clearwater. Enjoy the scenery and peaceful calm of a late-afternoon cruise on board a double-decker catamaran vessel with plenty of space to stretch out and soak up the breathtaking view. Watch a beautiful Florida sunset as the sun glows and gently settles into the Gulf of Mexico. Toast the new evening with a glass of Champagne.

Cruise out on the Gulf of Mexico and watch the sun dip below the horizon on this cruise from Clearwater. Sail along the Intercoastal Waterway, keeping an eye out for bottlenose dolphins and listening to commentary about your surroundings. Just as the sun is setting, guests 21 and older enjoy a champagne toast before sailing back to the dock.

Enjoy the exclusivity of a private boat trip for you and your party during this half- or full-day excursion. Your captain guides you through waterways for up-close views of wild dolphins and stops at secluded islands where you have time to relax on pristine beaches and swim in the Gulf of Mexico. Feel free to customize the itinerary with your captain to suit your group's interests. Price is per boat.

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 to the skies on a helicopter tour of Clearwater Beach and its surroundings. You'll have bird's-eye views of the white sands, turquoise water, Pier 60, golf courses, and the barrier islands. This is a great way to escape the crowds and gain another perspective on this popular vacation destination. Booking in advance means you won't risk a sold-out tour.

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.

You'll learn abot the history of Tarpons early days and the Vicorian influence 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"