Stock Island, Florida

Sunset Watersports is Key West’s Original Watersports Company, established in 1984, family-owned and operated for over 40 years. They offer a wide range of watersports activities including jet ski tours, sandbar charters, reef snorkeling, parasailing, dolphin watching, sunset dinner cruises, private charters, boat rentals, golf cart rentals, and Key West weddings on luxury catamarans for 2 to 149 guests, focusing on safety, fun, exceptional service, and best value.

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.

Barefoot Billy’s is a Key West charter business offering private catamaran charters for up to 6 passengers, exploring secluded sandbars, shallow reef patches, and tropical wildlife in the Florida Keys backcountry. Charters depart from locations including Casa Marina’s private beach, featuring custom outings with cushioned seating, cooler, and dive ladder for activities like snorkeling and sandbar visits.

Fury Water Adventures offers customizable private charter boat rentals on state-of-the-art catamarans in Key West, including half and full day options for groups. Charters can blend snorkeling, kayaking, sand bar relaxation, sunset viewing, catering, beverages, and more, with the largest fleet and deck space in Key West.

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.

Key West Paddle appears to be a paddle tour or charter business focused on kayaking, paddleboarding, and related water activities in Key West, such as mangrove tours, sandbar visits, and snorkeling, based on contextual search results referencing paddle charters; however, no direct information from http://www.keywestpaddle.com/ was available in the search results.

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.

Honest Eco Tours is a family-owned business based in Key West, Florida, specializing in authentic eco-friendly boat excursions designed by biologists. Founded in 2014 by a local biologist and his family, the company emphasizes genuine wildlife experiences in the National Wildlife Refuge, focusing on respectful and educational interactions with marine life. Their custom-designed boats, including the 37-foot catamaran SQUID, are engineered for safety, comfort, and environmental responsibility. With a commitment to small group sizes averaging eleven guests and a warm, hospitable atmosphere, Honest Eco Tours offers a unique and immersive way to explore Key West’s natural environment. The company provides a variety of multi-activity tours such as dolphin watching combined with guided snorkeling, kayaking through mangroves, sunset sails, and sandbar adventures. These tours cater to families, friends, and nature enthusiasts seeking an intimate and educational experience on the water. Guests enjoy expert-led wildlife interpretation, beginner-friendly snorkeling in calm waters, and organic refreshments aboard. Private charters are also available for personalized adventures, including pet-friendly options. With a focus on conservation and guest satisfaction, Honest Eco Tours delivers memorable excursions that connect visitors to the vibrant marine ecosystem of Key West.

Two Conchs Charters is a family-operated sportfishing business based in Marathon, Florida, with additional locations in Key West, Key Largo, Lighthouse Point, St. Augustine, and Oak Island, North Carolina. Founded by second-generation Florida Keys fishing guide Capt. Jack Carlson, who brings over 20 years of experience, the company is now run alongside his three sons, all professional captains. The fleet consists of more than 20 charter boats ranging from 17 to 43 feet, staffed by a team of expert guides dedicated to providing top-quality fishing experiences. Two Conchs is recognized for its extensive local knowledge, multi-generational expertise, and presence on prominent fishing networks such as the Sportsman Channel and World Fishing Network. The charters offer a wide variety of fishing adventures tailored to different skill levels and interests, including flats and inshore fishing for species like tarpon, bonefish, and snook, reef and wreck fishing targeting snapper and grouper, as well as offshore trips for pelagic species such as mahi-mahi, tuna, and marlin. Specialized excursions include bridge fishing for tarpon, deep Gulf trips for trophy catches, and even swordfish expeditions in the Atlantic. Beyond fishing, Two Conchs provides island eco and sandbar tours, fishing camps for skill development, and lodging options in Marathon. The company caters to novices and experienced anglers alike, emphasizing patient instruction and a fun, educational atmosphere on the water.

FishMonster & Island Jane, located in Key West, Florida, offers premium charter adventures specializing in sport fishing and island excursions throughout the Lower Keys. With over a decade of experience since 2006, this family-owned and operated business is known for its well-maintained, USCG-inspected vessels and professional, friendly crew. Their unique combination of offshore, inshore, and backcountry fishing options, alongside eco-tours and sunset sails, provides a comprehensive and authentic Florida Keys experience. The company’s commitment to safety, quality equipment, and personalized service sets it apart in the competitive Key West charter market. The business provides a diverse range of activities including offshore sportfishing for species like tarpon and grouper, light tackle fishing, flats and backcountry fishing, as well as split charters and party boat fishing aboard the stable twin-hulled FishMonster MAX. Island Jane Charters offers island adventures on vessels such as the Floridays and Looking Glass, featuring snorkeling, private eco-tours with clear kayaks, sandbar and dolphin excursions, and sunset cruises. These offerings cater to families, corporate groups, and fishing enthusiasts seeking a customizable and memorable day on the water in the clear, vibrant waters of Key West.

Get Up And Go Kayaking is a premier clear kayak tour company headquartered in Florida, with additional locations across Texas, Tennessee, and North Carolina. Established in 2016, it has grown into the world’s highest-rated clear kayak tour provider, known for its innovative transparent kayaks that allow paddlers to observe underwater wildlife and scenery in stunning detail. The company’s unique approach combines eco-friendly guided tours with expert local knowledge, offering an immersive experience through some of the most beautiful waterways, including Florida’s iconic springs and coastal areas. With over 30 locations and a commitment to conservation, the business stands out for its dedication to environmental stewardship and exceptional customer satisfaction, as reflected in thousands of five-star reviews. The company offers guided clear kayak tours suitable for paddlers of all skill levels, emphasizing small group sizes to ensure personalized attention and an intimate connection with nature. Guests can explore diverse ecosystems such as mangrove tunnels, hidden sandbars, and manatee habitats, all while learning about local flora and fauna from knowledgeable guides. Tours typically last around two hours and include safety equipment like life jackets, with tandem kayaks that can be adjusted for solo paddlers. Ideal for tourists and outdoor enthusiasts seeking a unique adventure, these tours provide a memorable way to experience wildlife and natural landscapes up close, with a strong focus on sustainable practices and wildlife conservation.

Key West Boat & Jet Ski Adventures is a premier watercraft rental and tour company located in Key West, Florida. Specializing in smaller group sizes, the business offers a more personalized and intimate experience compared to larger tour operators. With over 200 five-star reviews in just over a year, it stands out for its commitment to customer service and safety. The company partners with Sea-Doo to provide the latest jet ski models, ensuring high-quality equipment for all guests. Its unique approach includes guided jet ski tours, private boat charters, and eco-friendly kayak excursions, all designed to showcase the natural beauty of the Florida Keys. The company’s offerings cater to a wide range of customers, from families and couples to groups celebrating special occasions. Activities include freestyle jet ski rentals, guided jet ski tours suitable for all experience levels, kayak rentals and eco-tours, party boat charters, snorkeling trips, and dolphin tours. Private boat rentals feature spacious, custom-designed vessels equipped with premium water toys and amenities for a comfortable day or evening on the water. Whether exploring mangrove creeks, sandbars, or the vibrant coral reefs of Key West, guests enjoy a mix of adventure and relaxation with knowledgeable guides who enhance the experience through local insights and personalized attention.