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.

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.

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.

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.

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.

Classic Harbor Line offers private yacht charters on the 105-ft. Schooner America 2.0 in Key West, guiding guests through emerald green waters for daytime sightseeing sails, magical private sunset cruises, corporate events, birthday parties, weddings, anniversaries, and company outings. The U.S. Coast Guard-certified vessel accommodates up to 85 guests with bar and catering options, located in historic Old Town Key West.

SNUBA® Key West, located in Key West, Florida, has been offering unique underwater adventure experiences since 1999. As the only licensed SNUBA® provider in the area, the company specializes in introducing guests to the underwater world without requiring scuba certification. Their operations are supported by a fleet of well-maintained vessels, including the 47-foot luxury catamaran Good Times, equipped with modern amenities such as cushion seating, full marine head, fresh water rinse, and safety equipment. The experienced crew, consisting of certified rescue divers, divemasters, and instructors, ensures a safe and enjoyable experience for divers of all skill levels. SNUBA® Key West is also recognized for servicing major cruise lines, bringing thousands of visitors annually to explore the vibrant coral reefs and diverse marine life of the Florida Keys. The company offers a range of activities including SNUBA® diving, scuba diving, snorkeling tours, and dive training courses, catering to families, beginners, and certified divers alike. SNUBA® allows participants to breathe underwater using a surface air supply connected by a 20-foot hose, enabling exploration up to 20 feet deep without heavy scuba gear or prior certification. Guided by professional instructors, guests enjoy personalized underwater tours of notable dive sites such as Eastern Dry Rocks and Western Sambo, encountering colorful coral formations and abundant tropical fish. Additional services include underwater photography, private charters, cocktail cruises, and special event hosting, making SNUBA® Key West a versatile destination for adventure seekers and groups looking to experience the natural beauty of the Keys in comfort and safety.

Sunset Sail Key West is a locally owned and operated sailing charter company based in Key West, Florida, offering authentic and memorable sailing experiences on a fleet of classic vessels. With decades of sailing expertise and a deep passion for the sea, the company specializes in historic schooners and custom sloops, including the meticulously restored schooner When and If, which serves as the crown jewel of their fleet. Their commitment to genuine boatmanship and a personal approach sets them apart from typical party boats, providing guests with an intimate and elegant way to explore the crystal-clear waters of the Florida Keys. The company offers a variety of private and shared sailing charters tailored to different interests and group sizes, including two-hour sunset sails, day sails, snorkeling excursions, and custom trips such as stargazing or wildlife tours. Guests can choose from intimate cruises aboard historic yachts or private charters on the sloop High Tide, accommodating up to 28 or 12 guests respectively. Each sailing experience is led by knowledgeable local captains and crew who prioritize safety, comfort, and a genuine connection to the sea, ensuring that visitors enjoy a personalized and unforgettable adventure on the water.

Located in Key West, Florida, Argo Navis is a 75-foot luxury catamaran and the last commercial sailing vessel constructed in the city. Operating year-round from the Key West Historic Seaport, it offers a unique sailing experience where guests can enjoy the tranquil beauty of the Atlantic Ocean meeting the Gulf of Mexico. The vessel stands out for its spacious design, ensuring no overcrowding, and its commitment to providing a serene atmosphere without music, allowing passengers to fully appreciate the natural surroundings. As part of the Hindu Charters family, Argo Navis combines local heritage with modern luxury, making it a distinctive choice for sailing enthusiasts and visitors alike. Argo Navis provides a variety of sailing experiences including Sunset Cruises, Brunch Sails, Day Trips, and Special Events, all featuring carefully curated craft beers, cocktails, fine wines, and a range of light to hearty menu options. The catamaran is also available for private charters, accommodating weddings, corporate meetings, classes, and other special occasions with personalized service and attention to detail. Guests can expect an intimate and relaxed atmosphere with ample space to stretch out and enjoy the scenic views, complemented by offerings such as charcuterie-style appetizers and bean-to-bar chocolates selected with sommelier guidance. The vessel’s dog-friendly policy further enhances its appeal to a broad range of customers seeking a memorable maritime experience in Key West.

Dolphin Safari Charters is a family-owned business based in Key West, Florida, specializing in intimate dolphin watching and snorkeling tours since 2005. Recognized by National Geographic Travel and featured in local guides, the company offers a unique small-group experience with a maximum of six guests per boat, ensuring personalized attention and respectful encounters with wild dolphins. Departing from Perry Hotel Marina on Stock Island, just minutes from downtown Key West, their tours are led by experienced local captains who provide expert knowledge of the best dolphin habitats and pristine coral reefs. This approach distinguishes them from larger commercial operations by focusing on comfort, safety, and an authentic connection to the marine environment. The company’s offerings include morning dolphin watching tours, vibrant reef snorkeling adventures, and private boat charters that can be customized to combine dolphin encounters, snorkeling, and visits to secluded Florida Keys sandbars. All tours provide necessary snorkeling gear and refreshments, creating a hassle-free experience suitable for families and visitors of all skill levels. Their private charters aboard the boat Vitamin Sea allow guests to tailor their day on the water, whether chasing dolphins, exploring hidden islands, or relaxing on quiet sandbars. With a commitment to eco-friendly practices and a family-oriented atmosphere, these tours deliver memorable, crowd-free excursions that highlight the natural beauty and wildlife of the Florida Keys.

Lost Reef Adventures is a premier scuba diving and snorkeling company based in Key West, Florida, with over 40 years of local expertise. Located at the Key West Bight Marina, this PADI 5-Star Dive Center specializes in small, personalized reef trips that explore North America’s only living coral reef. The company is known for its professional and friendly crew, commitment to safety, and access to world-class dive sites such as the famous Vandenberg wreck. Their extensive experience and local knowledge ensure that every guest, from beginners to advanced divers, enjoys a unique and memorable underwater adventure. The company offers a variety of services including twice daily snorkeling and scuba diving excursions, scuba instruction, and specialty courses like the PADI Resort Course and Open Water certifications. All snorkeling and diving gear is provided, with options for equipment rental and purchase available at their full-service dive shop. Lost Reef Adventures caters to families, first-time snorkelers, certified divers, and those seeking advanced training, providing expert guidance and comfortable, safe experiences in the clear tropical waters of Key West. Additional offerings include sunset cruises and special event hosting, making it a versatile choice for visitors looking to explore the vibrant marine life and coral reefs of the area.