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.

FishMonster Charters & Island Jane offers premium charter adventures in Key West and the Lower Keys, including offshore sportfishing, light tackle fishing, flats/backcountry fishing, split charters, MAX party boat fishing, snorkeling adventures, sunset cruises, private eco tours with clear kayaks, sandbar/dolphin excursions, family fun days, lobstering, and weddings. Family-owned and operated since 2006, with well-maintained USCG-inspected vessels and professional crew departing from A&B Marina at 700 Front St, Key West, FL 33040.

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 is the only licensed SNUBA company in Key West, Florida, founded in 1999, offering underwater experiences without scuba certification using a surface-supplied air hose. They provide private charters, scuba training, party cruises, cocktail cruises, boat tours, sunset weddings, special events, snorkeling, scuba diving, and custom excursions for groups up to 49 guests on their flagship vessel Good Times, serving locals, vacationers, and major cruise lines.

Sunset Sail Key West is a locally-owned fleet of historic sailboats in Key West, Florida, offering exclusive small-boat private and shared sailing charters with experienced captains. They provide authentic sailing experiences including sunset sails, snorkeling, daysails, weddings, private parties, sunrise toasts, full moon sails, and custom requests, emphasizing intimacy, flexibility, and away from crowds on vessels like the 33ft sloop High Tide, 50ft ketch Conch West, 32ft schooner Free Spirit, and guest ship When and If (up to 32 guests).

Argo Navis Key West Sailing Charters is a family-owned business operating a 75-foot luxury catamaran, the last commercial sailing vessel built in Key West, Florida. It offers year-round intimate, all-inclusive sailing experiences from Key West Historic Seaport, including sunset cruises, brunch sails, day sails, sandbar sails, and private charters for events like weddings, corporate retreats, and celebrations, featuring curated food and drink pairings in a music-free, uncrowded environment.

Salty Soul Charters is a private charter boat company in Key West, Florida, offering customized private boat charters to explore the island by water, including full day trips, half day adventures, sunset cruises, and special occasion charters like birthdays, proposals, and weddings. Guests can customize itineraries from listed excursions, encounter wildlife such as turtles, dolphins, and sting rays, visit sandbars and mangroves, with options for snorkeling and fishing.

The Schooner Spirit of Independence is a family-owned and operated classic sailing schooner since 1972, offering 2-hour sunset sails from Key West's Historic Seaport. It provides an intimate sailing adventure with five-star service, complimentary beverages like champagne, mimosas, wines, and beers, plus turkey focaccia sandwiches. Limited to approximately 26 passengers on a U.S. Coast Guard licensed vessel for up to 49, it features a steel hull for stability, storytelling by the crew, and options for public cruises or private charters for weddings, events, and gatherings. Built in 1800s style with exotic hardwood interior, it teaches seamanship to scouts.

The Key West Cocktail Cruise offers 2-hour adults-only sunset cruises on a spacious 47-foot catamaran, featuring all-inclusive craft beer, fine wine, and hand-crafted cocktails with premium spirits, hand-made mixers, and fresh-squeezed juices. Custom charters, sailing excursions for bachelor/bachelorette parties, weddings, and special events are available in Key West and the Florida Keys, with options for SNUBA, snorkel, scuba add-ons, and sandbar parties.