Calypso Breeze Evening Casual Cruise
Sail Madeira Beach with music, dancing, and an optional tropical dinner buffet
From$59/ personincl. taxes and fees
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Discover what we've curated for you
Sail Madeira Beach with music, dancing, and an optional tropical dinner buffet
Discover what we've curated for you
2 hours
Complimentary drinks w/ buffet, DJ
Sail the calm waters off Madeira Beach on a casual evening cruise. Enjoy music, dancing, tropical drinks, and an optional island-style dinner buffet.
Boarding begins 30 minutes before departure. Resort-casual attire is recommended; avoid swimwear and tank tops. Infants ages 2 and under must be included in the reservation.
Cruise fares are non-refundable. If you miss your departure, fares are not refundable or reschedulable. For regularly scheduled cruises, rescheduling requires at least 24 hours’ notice. For special event and holiday cruises, no refunds or rescheduling are permitted.
John's Pass Village & Boardwalk; 177 Boardwalk Pl. E., Madeira Beach
StarLite delivers consistently memorable experiences on the water, with guests returning year after year for good reason. The crew stands out repeatedly in reviews, with servers like Jennifer, Lauren, Stephanie, and Makenna earning specific praise for their attentive, personable service. The food exceeds expectations for most guests, from lunch cruises to elaborate five-course New Year's Eve dinners, though a few mention occasional issues with meat preparation. Multiple reviewers spot dolphins along the way, and the captains keep everyone informed and entertained throughout the journey. What really shines through is how the company handles challenges. During rough weather at Gasparilla, management arranged trolleys back to port rather than subjecting guests to a choppy return trip, the kind of thoughtful decision that earns loyalty. The atmosphere works for everything from intimate celebrations to a 42-person birthday party, with dancing, drinks, and beautiful waterway views. One guest mentioned the DJ being lackluster, but most rave about the music and overall vibe. After two decades of loyal customers and special occasion celebrations, it's clear this operation knows how to create experiences worth repeating.
My family of four just completed the 2026 Gasparilla Cruise and Parade. Everything went perfectly, well except for the weather, so Nature only gets two stars for that. The boarding process was quick. Our assigned table was already set up with various fruits and yummy muffins when we arrived. Our server, Jennifer was very attentive, repeatedly asking if we needed anything throughout the day. Lunch and dinner were better than I expected. The offerings were broad-based, so it would have been hard not to find something you liked. The captain timely informed us of the itinerary, which required some changes due to the extreme weather. Kudos to the management for pre-arranging trolleys to take everyone back to Port St. Petersburg from Gasparilla, at considerable expense, no doubt. I have been a boater for over 50 years, and I was not looking forward to the return trip in 35 mph winds and 4 ft. seas. Lastly, kudos to the crew as well. There they were with the wind chill in the 30s, sincerely greeting and guiding everyone off the ship, and thanking everyone for coming. Arrrg!Count me in for next year.
Cabana Key
February 1, 2026
My family of four just completed the 2026 Gasparilla Cruise and Parade. Everything went perfectly, well except for the weather, so Nature only gets two stars for that. The boarding process was quick. Our assigned table was already set up with various fruits and yummy muffins when we arrived. Our server, Jennifer was very attentive, repeatedly asking if we needed anything throughout the day. Lunch and dinner were better than I expected. The offerings were broad-based, so it would have been hard not to find something you liked. The captain timely informed us of the itinerary, which required some changes due to the extreme weather. Kudos to the management for pre-arranging trolleys to take everyone back to Port St. Petersburg from Gasparilla, at considerable expense, no doubt. I have been a boater for over 50 years, and I was not looking forward to the return trip in 35 mph winds and 4 ft. seas. Lastly, kudos to the crew as well. There they were with the wind chill in the 30s, sincerely greeting and guiding everyone off the ship, and thanking everyone for coming. Arrrg!Count me in for next year.
Cabana Key
February 1, 2026