Trips with Second Wind Marine are all about gaining a new perspective; mainly of Florida's western coast. Commanding a 25-foot Bennington pontoon boat, Captain Charlie leads groups of up to six out onto the waters of the Gulf of Mexico as they relax, sightsee, or even fish. The vessel comes equipped with a Bluetooth connection as well as a WiFi hotspot?small creature comforts for folks to enjoy as they cruise the waves and enjoy any drinks or snacks they brought aboard. For a more immersive experience, Captain Charlie ferries passengers to snorkel sites in the Gulf, and leads charters to deep waters for those fishing for the really big boots.
Siesta Key Paddleboards' staff uses paddleboards to unlock adventures across the Gulf of Mexico and Sarasota Bay. They drop off and pick up paddleboard rentals at the area's sandy beaches, where groups can spend days floating atop Florida's blue-green waters and Jell-O–filled tide pools. For novices, instructors lead private and group sessions that teach the finer points of balancing on boards. The crew members also draw on their knowledge of local areas to lead tours, which pass by celebrity homes, through canals, and into hidden mangroves populated by aquatic wildlife.
Mark Toomey once helmed his own recruitment firm in Nottingham, England, on the outskirts of Sherwood Forest, but a disdain for damp winters led him to the sun-drenched beaches of Siesta Key. Since opening Robin Hood Rentals in 2009, Mark has persevered through what he calls "Florida's harshest winter in 30 years," during which temperatures teetered near the freezing mark. He equips visitors with rental land-based and aquatic craft that let them explore the area without having to saddle a horse or propose to a dolphin.
From its perch near the Jim Neville Marine Preserve, the company fits cyclists with a range of beach, mountain, and tandem bicycles; matches riders to a fleet of two-seat 49cc automatic scooters; and trains visitors to venture off on newer-model i2 LeanSteer Segways. They also let kayakers explore the local waterways from sunrise into the nighttime.