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Calypso Tropical Cruises


Tropical Dining, Sightseeing & DJ Party Cruises 
in Clearwater & Madeira Beach, FL

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A Calypso Tropical Cruise brings island vibes to life! Enjoy a fun, casual cruise with a casual buffet vibrant atmosphere, and stunning ocean views. By day, relax with lunch and sightseeing; by night, dance to DJ beats on a lively party cruise. Select cruises include complimentary beer, wine, and rum punch with your buffet ticket! We also offer group events, weddings, and holiday specials. Find your ideal getaway and book your adventure today!

Evening Cruise

Groups Events

Daytime Cruise

Wedding & Receptions

Specialty / Holiday Cruises

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Meet Our Fleet

Calypso Queen

Step aboard the Calypso Queen—a lively, 65-foot Caribbean-style cruise ship made for relaxing sightseeing, lunch, or dinner along the intracoastal waterways. It features two air-conditioned indoor dining decks, an open-air top deck with waterfront views, two full-service bars, a galley, restrooms on both dining levels, and a state-of-the-art sound system.

Map Marker Clearwater Beach, FL

Users Up to 150 passengers

Four images of a tropical-themed riverboat with outdoor deck, interior seating, and sunset silhouette.

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Calypso Breeze

Climb aboard the Calypso Breeze—a vibrant, 68-foot Caribbean-style cruise ship perfect for laid-back sightseeing, lunch, or dinner on the intracoastal waterways. Enjoy two air-conditioned indoor dining decks, an open-air top deck with stunning views, full-service bar, galley, restrooms, and a top-notch sound system.

Map Marker Madeira Beach, FL

Users Up to 150 passengers

Yellow ferry with palm decor, rooftop seating, indoor dining, and colorful drinks.

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The StarLite Family

StarLite Dining Yachts

An unforgettable evening on the water with chef-prepared entrees, panoramic coastal views, and lively music.

 

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Dolphin Racer

Enjoy a thrilling, narrated Dolphin Racer cruise with guaranteed dolphin sightings—or your next ride is free! Watch dolphins jump & surf through the Gulf Beaches.

 

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Tiki Island Cruises

As you embark on this tiki tour, your friendly boat crew will share fun facts and interesting stories about the area’s rich history, famous residents and harbor landmarks.

 

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Top-Rated Cruises in Clearwater & Madeira Beach, FL