Top Clearwater Cruises & Sailing

You'll find a wide variety of Clearwater cruises from dolphin tours to sunset cruises—and even a floating tiki bar tour. These are the cruises that receive the highest reviews and ratings from prior guests: 

• Little Toot Dolphin Adventure at Clearwater Beach
• Clearwater Encounters with Dolphins Tour
• 2 Hour Sunset Cruise in Clearwater, Florida
• Mega Bite Dolphin Tour Boat in Clearwater Beach
• Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Yes. Getting out on the water when visiting Clearwater is a favorite activity for visitors as you’ll get to see marine life and a variety of birds up close. These cruises are very budget-friendly and offer a relaxing way to see more of the Gulf Coast.

The price for these cruises typically averages around US$40 per person with discounted tickets available for kids. Private cruises typically charge a per-group rate that ranges from US$300 to over US$1,000 depending on the length of time and itinerary.

Yes, Clearwater’s location on the Gulf Coast typically provides clear and calm waters ideal for sailing. You can book a sunset or half-day sailing excursion that takes you between the barrier islands to sail offshore where you might even spot some friendly dolphins.

Casual clothing with sun protection is typically sufficient for most Clearwater cruises, while sunset cruises can be a bit dressier. You’ll want to wear shoes that are sturdy and slip-resistant (no high heels) as the deck may get wet. If your cruise includes an opportunity to swim, wear your swimsuit and bring a towel and sun cover-up.

While seeing dolphins is never guaranteed, you can often see these playful marine animals on a Clearwater cruise once you head out of the marina. Your captain will likely take you to areas where these animals are typically spotted.

There are tons of fun tours and excursions in Clearwater aside from cruises and sailing trips. According to previous travelers, these are the best activities to book for your next trip:

• Sunset Cruises 

• Snorkeling

• Kayaking

• Glass Bottom Boat Tours

• Ghost Tours

Prices vary for Clearwater cruises and sailing trips depending on the duration and inclusions. If you’re looking for high-quality experiences on the lower end of the price range, these are the best tours to book now: 

• Clearwater Daytime Yacht Sightseeing Cruise with Optional Dining

• Shark Teeth and Shells, Dolphin and Shelling Tour Boat Clearwater Beach

• Mega Bite Dolphin Tour Boat in Clearwater Beach

• !! Flippers Fun Boat !! Dolphin Adventure Clearwater Beach!

• Clearwater Evening Yacht Cruise with Optional Dining

There are plenty of Clearwater cruises to choose from, so take time to find one that fits your group and interests, whether it’s a relaxing sunset sail, a family-friendly pirate cruise, or a dolphin-watching tour. Some cruises include food, drinks, or entertainment, while others don’t—check the tour description carefully before booking to find one that suits your needs best.

To make the most of your Clearwater cruise or sail, dress for the weather—bring sunscreen, sunglasses, and a light jacket for cooler breezes on the water. Arrive early to get the best seats and avoid last-minute stress. Pack binoculars for wildlife to enhance your experience, and don’t forget your camera. Bring a valid ID if drinks are served, and a small cash to tip the crew.

The best time to book Clearwater cruises is in the summer and fall, especially October and November, when the weather is warm, humidity drops, and crowds thin out. You’ll also enjoy calmer waters and better availability. Cruises run year-round, and while summer is lovely, a fall booking offers a more relaxed experience on and off the water.