What you'll do:

Celebrate your bachelor or bachelorette weekend with tropical drinks, food, music, dancing, waterfront views, and island-style fun aboard the Calypso Breeze. Plus enjoy complimentary beer, wine, and rum punch with buffet purchase! This casual evening cruise from John’s Pass is perfect for groups that want something festive and easygoing without planning another ordinary dinner reservation.

The Calypso Breeze is a colorful, Caribbean-themed, triple-deck cruise boat with enclosed dining levels, an open-air top deck, DJ entertainment, and an optional tropical island-style buffet. Buffet tickets include complimentary beer, wine, rum punch, and soft drinks, with full bar service and desserts available for purchase onboard.

Why we love it for your party:

• Tropical party cruise energy - A fun, casual way to celebrate on the water with music, drinks, dancing, and island vibes.

• DJ entertainment - The live DJ plays island favorites and today’s top hits, creating an easy celebration atmosphere for groups.

• Optional island-style buffet - Guests can add a tropical buffet with items like mango-glazed chicken, beef teriyaki, chilled shrimp, blackened white fish, pulled pork, rice, beans, fruit, salad, and more.

• Beer, wine, rum punch, and soft drinks included with buffet tickets - A major win for party groups, as long as guests book the buffet option.

• Open-air top deck - Perfect for waterfront views, photos, fresh air, and taking in the Madeira Beach scenery.

• Enclosed, air-conditioned dining levels - A great comfort feature for Florida weather, especially for groups dressed up for a celebration.

• Perfect for bigger groups - The Calypso Breeze is Coast Guard approved to carry up to 150 passengers, with each dining level seating up to 75 guests.

• John’s Pass location - The cruise departs from John’s Pass Village & Boardwalk, making it easy to pair with shopping, bars, restaurants, beach time, or a full bach weekend itinerary.

About this experience partner:

Calypso Tropical Cruises is part of the Starlite Cruises family, offering casual island-style cruises from Clearwater Beach and Madeira Beach. The Calypso Breeze brings the tropical party experience to John’s Pass with a colorful Caribbean-themed vessel, DJ entertainment, an optional island-style buffet, drinks, dancing, and waterfront views.

The Calypso Breeze is designed for casual sightseeing, lunch, and dinner cruises along the intracoastal waterways, with two enclosed air-conditioned dining levels, an open-air third deck, restrooms, a full-service bar, galley, and sound system.

Additional information:

• Location: John’s Pass Village & Boardwalk, 177 Boardwalk Pl. East, Madeira Beach, FL 33708

• Duration: 2 hours

• Cruise type: Evening casual tropical cruise

• Vessel size: 68-foot triple-deck cruise boat

• Age: All ages welcome; guests must be 21+ with valid ID to consume alcohol

• Included with Buffet Ticket: 2-hour inland water cruise, Tropical island-style dinner buffet, Complimentary beer/wine/rum punch/soft drinks

• Available for purchase: Full bar service and desserts

• Boarding: Boarding begins 30 minutes before departure

• Check-in: Check in at the ticketing window located next to the entrance of the parking garage

• Accessibility: Some areas of the vessel are only accessible by stairs

• Weather: Cruises generally operate rain or shine, subject to captain / Coast Guard discretion

• Late arrivals: Missed departures are not refundable or reschedulable unless purchasing trip protection.