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.

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 Bottom Boats offers customizable private boat charters in Key West, Florida Keys, with two vessels: a Classic Party Boat accommodating up to 36 guests for large celebrations like birthdays, bachelor parties, and corporate events, featuring a loud sound system, onboard bathroom, USB charging, and sandbar parties; and an Eco Tiki Vessel for up to 12 guests for intimate nature explorations, romantic sunset cruises, and backcountry trips with authentic tiki design and shallow-draft access. Charters are 4 or 6 hours, fully customizable to destinations like Boca Grande, Snipes Keys, Jewfish Basin, Mud Keys, backcountry, and open waters, including excursions such as sandbar socializing, dolphin watching, floating, island hopping, and cruising.

Tiki Boat Adventures offers private tiki bar boat charters in Key West, FL, featuring USCG-approved 20-foot custom tiki boats for sandbar trips, sunset cruises, harbor tours, bachelor/bachelorette parties, birthdays, and other celebrations. Guests enjoy relaxing under thatched canopies with onboard amenities like a bathroom, cooler, Bluetooth speakers, and a tiki bar, accommodating up to 6 guests per boat for personalized water adventures in the turquoise waters of the Florida Keys.