Outback with Jack

Outback with Jack offers private, customized backcountry charters in the Lower Florida Keys, departing from Sugarloaf Key. Led by Captain Jack, a Florida Keys native, the business introduces guests to the area’s calm, shallow waters, secluded sandbars, mangrove tunnels, and local wildlife. Charters take place aboard a 26-foot tritoon and accommodate up to six people, with experiences tailored to each group’s interests.

Guests can choose fishing for species such as snapper, grouper, and sea trout, or enjoy a sandbar outing with time to swim, relax, and explore. During the appropriate season, Captain Jack also guides hands-on lobster diving and crabbing trips, including snorkeling and help locating a catch. The company describes its adventures as all-inclusive, with fishing gear and guidance provided for fishing excursions.

Private options include four-hour and six-hour customized trips, with base prices covering up to four guests and additional charges for extra passengers. Special charter requests may also be arranged.