Lazy Dog Adventures is a Key West-based charter business offering kayak and stand-up paddleboard tours, rentals, lessons, paddle yoga, paddle fit, and backcountry boat trips including sandbar charters. They focus on exploring the quiet side of Key West's mangrove ecosystem, sea grass beds, and sandbars with experienced guides, operating year-round from Hurricane Hole Marina.

Hurricane Hole Key West, Florida offers a full service marina, restaurant, dockside bar, watersports, and fishing charters. Located on Cow Key Channel with easy access to the Atlantic Ocean and Gulf of Mexico, it provides dockage for vessels up to 34 feet, ethanol-free gasoline, live/frozen bait, tackle, and an on-site dive shop. Known locally as 'The Hole', it is a one-stop spot for dining, recreation, and boating activities from sunup to sundown.

Geiger Key Marina is a waterfront marina, RV park, and fish camp offering boat slips, fuel, rentals, fishing charters, kayak and paddleboard rentals/tours, an on-site restaurant serving locally sourced seafood, showers, laundry, and access to Florida Keys fishing reefs and mangroves.

Sunset Watersports, located in Key West, Florida, is the island’s original and longest-standing watersports company, established in 1984. With over 40 years of experience and more than 18,500 five-star reviews, it has built a reputation as a trusted, family-owned provider of premier watersport excursions. The company is known for its commitment to world-class customer service, top-quality equipment powered by Mercury Marine engines, and a carefully curated selection of the best island experiences. Its unique position as the oldest parasail company in the United States and its extensive range of activities set it apart in the competitive Key West tourism market. The company offers a wide variety of watersport activities and tours designed for all ages and skill levels, including guided jet ski tours, parasailing, snorkeling trips, sunset and dinner cruises, eco kayak adventures, sandbar charters, dolphin watch tours, and golf cart rentals. Notable offerings include a 28-mile jet ski tour around Key West with multiple stops at iconic locations such as the Southernmost Point and Boca Chica Sandbar, as well as the only air-conditioned dinner cruise on the island featuring a tropical buffet and open bar. Guests can also enjoy self-driven mini speed boats, eco-friendly kayak tours through mangrove islands, and family-friendly dolphin encounters. Each experience is designed to provide memorable, safe, and engaging adventures that showcase the natural beauty and unique culture of Key West.

Kayak Kings of Key West offers exhilarating kayaking activities and fun, unique guided tours through mangrove tunnels and mazes in Key West, featuring wildlife like nurse sharks, jellyfish, and manatees. They provide 2-3 hour tours including sunrise, sunset, and upcoming adventures like sandbar parties and treasure hunts, along with kayak and paddleboard rentals.