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   [Boating Lifestyle](/articles/boating-lifestyle)# Captain Trip Smith's Exploring Paradise - The Florida Keys

 Nov 01, 2026

 

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### Cutwater 288CB Keys Exploration

Join Captain Trip Smith and his son as they transition from a challenging ICW journey into the vibrant, aqua-blue paradise of the Florida Keys aboard their new Cutwater 288CB. This video serves as the definitive reward for their three-day slog, demonstrating precisely why this pocket cruiser is engineered for extended family exploration.

The adventure begins by dialing in the vessel’s systems, utilizing Bluetooth monitoring for the lithium battery bank and verifying fuel burn calculations, confirming the boat’s efficient one-mile-per-gallon range. Underway, they navigate Tavern Creek to transition from the Gulf to the Atlantic side, showcasing the 288CB's ease of handling. Despite rolly conditions at Alligator Reef Lighthouse, the crew anchors successfully for a snorkeling session, enjoying the remarkably clear waters.

A critical seammanship moment arises when a careless boater anchors dangerously close, forcing Captain Trip to execute a careful and assertive anchor retrieval in rough seas. This segment provides an invaluable real-world lesson on situational awareness and etiquette. The mood shifts back to family fun as they spot wild sea turtles mating, paddleboard through serene mangrove tunnels, and discover a massive secret stash of lobsters (over 40!) in an underwater barrel.

Cap Trip concludes by highlighting the 288CB’s clever design features, including the convertible cockpit seating and standard-equipment paddleboard storage, defining what the ultimate Florida Keys cruising experience looks like. It's a blend of necessary captain's knowledge, breathtaking exploration, and quality family time in a truly unique destination.

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## About Capt. Trip Smith

Capt. Trip Smith is one of BoatTEST.com's lead captains and marine journalists. With years of experience testing hundreds of boats, Trip combines real-world boating knowledge with BoatTEST's rigorous performance-testing methodology. His reviews go beyond the specifications, covering handling, ride quality, comfort, design, and how each boat performs in real-world conditions, helping boaters make informed buying decisions.

**Follow Capt. Trip Smith on YouTube for more in-depth boat reviews, walkthroughs, and boating adventures:**  
[*Subscribe to Capt. Trip Smith's YouTube Channel*](https://www.youtube.com/@TripSmith)