Whether you’re planning for spring break or a seasonal getaway in the winter or summer, Clearwater Beach vacation rentals are perfect year-round. Nestled on Florida’s Gulf of Mexico coastline, this seaside town features sugar-white beaches, family-friendly events, educational attractions, fun local food, and much more. Without further ado, here are the 10 most popular things to do in Clearwater Beach.

1. Go Dolphin Watching

Little Toot is an authentic tugboat that can enter the shallows as well as the Gulf waters to see more dolphins and get your closer to them. It’s the vessel’s shape and power that creates a huge wake in which dolphins love to jump and party. Catch the breeze under the large canopy or bask in the sun on this 40-foot tug. The bar serves soft drinks, water, and beer, and there are restrooms onboard.

2. Join a Pirate Crew

If your Clearwater Beach vacation rental evokes the inner pirates among your crew, there’s a cruise for you. Board the Pirate’s Ransom with your little buccaneers for a dolphin-watching, swashbuckling adventure. The vessel is a replica Spanish galleon, complete with a Jolly Roger flag, cannon, and a pirate crew. Outfit your little pirates with hats, swords, and eye patches to prepare them to join the pirate crew and participate in the shenanigans. When you board the ship, the crew hands you a complimentary cocktail; then they set out to entertain the kids with games, songs, and water pistol battles for a memorable voyage on the high seas.

3. Tour Clearwater Beach on a Segway

See Clearwater Beach’s best attractions by joining The Segway Adventure for a guided tour that begins on the Beachwalk. The seven-and-a-half mile trek takes you up the Clearwater Memorial Causeway, with a scenic stop at the top. Next, you ride down the two-story circular sidewalk to the Clearwater Beach Marina. From there, you move on to the Harbor Oaks area where you see historic home sites that are over a century old. The tour takes a second break on the Harbor Oaks public fishing dock before you ride back across the Causeway to the beach.

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4. Experience Vertical Flight

Vertical Flight defies gravity, powers up in a vertical lift, settles gently into a hover, then departs from Clearwater Airpark’s helipad for your sightseeing tour, photo flight, manatee spotting, or sunset flight. Choose a tour that lasts between 12 and 60 minutes, or plan a customized tour with your pilot. Tours include flights along the Dunedin Causeway to Honeymoon Island, along Caladesi Island, and returning to Clearwater Beach via the Memorial Causeway. Longer flights add Fort Desoto Park and then circle the center span of the Skyway Bridge over Tampa Bay.

5. Taste Some Local Wines

Aspirations Winery bottles more than 25 different types of wine, including fruit-infused wines, dry reds, whites, and dessert wines. The grapes come from the finest grape growing regions around the country, and some from around the world. The small batches and their own recipes ensure that Aspirations Winery creates consistent-tasting bottles of wine year after year. Take a bottle or two back to your Clearwater Beach vacation rental to enjoy as you watch a spectacular sunset on your deck.

6. Catch the Party on Pier 60

When you look for attractions around Clearwater Beach, you can get so much more than just some sand between your toes at Pier 60. The 1,080-foot fishing pier and recreational park include restrooms, telescopes, a well-equipped playground, and several covered pavilions. The bait house offers drinks and snacks, rental equipment, souvenirs, fishing tackle, and bait. Sunsets at Pier 60 on Clearwater Beach feature daily festivities with artisans, crafters, and street performers two hours before until two hours after sunset.

7. Visit Clearwater Marine Aquarium

As a rescue and rehabilitation center for dolphins and sea turtles, Clearwater Marine Aquarium offers hands-on learning opportunities for families who want to understand the process. This tour includes VIP seats for the dolphin show. Dolphin lovers age three and older get the chance to don wetsuits, masks, and snorkels and interact with Atlantic Bottlenose dolphins. Participants receive a photo to take home.

8. Set Forth on a Treasure Kwest

A Treasure Kwest is a self-guided, interactive sightseeing tour that uses your smartphone to solve pirate-speaking clues, riddles, and puzzles to explore places, activities, and local businesses. It’s a fun way to learn about the city as you stroll along the beach and through the town. The Level 1 Kwest is designed for younger families, featuring untimed clues, riddles, and puzzles that are easier to solve, such as finding the smiling turtle. The Level 2 Mystery Treasure Kwest is for adrenaline junkies who like challenges and racing against the clock. Depending on the level and your pace, you walk up to three miles in about two-to-four hours.

9. Watch Car Racing

You don’t have to live life in the fast lane to enjoy watching the speed races at Show Time Speedway. Even with 4,000 grandstand seats, there’s still room for your lawn chairs and blankets. While coolers and snack foods aren’t carried into the grandstand area, you can enjoy lots of concession drinks and treats. If you enjoy tailgating, bring your grills, foods, and coolers and set up in the back-stretch parking area.

10. Explore the Art Galleries

From wildlife paintings to glass casting, and wine with art, Clearwater galleries captivate both the locals and visitors. Art & Wine Gallery on Clearwater Beach invites you to enjoy sipping your choice of wines and peruse the artwork on display. Just across the bridge, Robert Schoeller Fine Art combines a studio and gallery. Visit to enjoy his paintings of Native American art, landscapes, and tree paintings or to commission a custom portrait from a photo. Around the corner, the Marlene Rose Gallery features the artist’s works in glass. As one of the few women who work in glass cast, her pieces include butterflies, African pieces, abstracts, bells, and much more.

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