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.

Robbie’s of Islamorada is a premier marina and activity hub in the Florida Keys, renowned for its world-famous tarpon feeding experience. It offers fishing charters, snorkeling, jet-ski adventures, sunset cruises, boat rentals, kayaking, paddleboarding, and more for families and adventure seekers.

Hawks Cay Resort Marina offers Florida Keys fishing charters with knowledgeable captains providing inshore and offshore trips for species like sailfish, bonefish, mahi mahi, swordfish, and snook, along with other marina activities including snorkeling, sunset cruises, and SCUBA.

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.

Thousand Trails is a comprehensive network of over 200 campgrounds and resorts located across North America, offering year-round outdoor recreational opportunities in diverse and scenic destinations such as North Carolina’s Crystal Coast, Oregon’s Mount Hood, and Florida’s Keys. With decades of experience in providing quality camping experiences, the company caters to a wide range of campers, from weekend visitors to full-time adventurers. Its unique appeal lies in the variety of accommodations available, including spacious RV sites with full hookups, cozy cabins, glamping tents, and tiny houses, all supported by well-maintained facilities and a commitment to excellent service. The campgrounds are situated in prime locations that provide easy access to natural attractions, beaches, hiking trails, and local points of interest, making each stay both convenient and memorable. The offerings at Thousand Trails are designed to accommodate diverse preferences and group sizes, including pet-friendly options and age-qualified communities for those 55 and older. Guests can choose from nightly, weekly, monthly, or seasonal stays, with membership plans available to enhance affordability and flexibility. Each campground features a broad range of amenities such as swimming pools, fitness centers, dog parks, pickleball courts, and organized social activities like live music, tournaments, and themed events. Whether visitors seek relaxation by the beach, outdoor adventures like fishing and boating, or family-friendly entertainment, the experience is enriched by attentive staff and a welcoming community atmosphere. This combination of extensive amenities, scenic locations, and customizable stay options makes Thousand Trails a preferred destination for campers seeking both comfort and connection with nature.

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.

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.

Manic Sportfishing is a Marathon, Florida charter business specializing in private fishing charters, reef and offshore trips, sunset cruises, island tours, snorkeling, and family-oriented excursions on safe, clean boats with experienced captains and mates. Owned by Captain Greg Fabrizzi, it offers various vessels for hardcore anglers, trophy hunting, sightseeing, and affordable group activities.

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.