Sweet Liberty Catamaran Sailing & Boat Tours

Sweet Liberty has sailed out of Naples City Dock in Crayton Cove since 1991, making it one of the longest-running sailing charter operations on the Naples waterfront. The company’s main vessel is a 53-foot sailing catamaran, a boat large enough to carry a good-sized group while still sailing under wind power for at least part of most trips, which sets it apart from the mostly power-driven fishing and sightseeing boats that share the same dock.

The standard cruise lineup includes sunset sails, timed to Naples Bay’s reliable Gulf Coast evening light, along with shelling excursions that run out to nearby barrier islands and sandbars where guests can walk the beach and collect shells during a stop in the trip. General sightseeing cruises round out the daytime schedule, covering the bay’s mangrove shoreline and the waterfront homes that line much of the route between the city dock and Gordon Pass.

Beyond the catamaran, Sweet Liberty operates the Sweet Tiki, a smaller six-passenger floating bar boat that functions more like a mobile lounge than a traditional tour vessel, giving the company a second, more intimate product alongside its larger group cruises. Both vessels are available for private charter, and the company markets itself for weddings, corporate events and even memorial services, a niche that reflects how a boat on Naples Bay can double as an event venue with a built-in scenic backdrop.

Booking runs through the company’s own site using an online reservation system, standard practice among the more established charter operators at the city dock, and pricing varies by cruise type and length rather than following a single flat rate. The Crayton Cove location, tucked into the historic Naples City Dock area, places Sweet Liberty within walking distance of Third Street South’s restaurants and shops, making it easy to pair a sunset sail with dinner downtown afterward.

With more than three decades in business at the same dock, Sweet Liberty has built a name recognizable to longtime Naples visitors and residents, and it remains one of the few sail-powered charter operations working out of a waterfront otherwise dominated by power boats. That combination of a genuine sailing catamaran, a long operating history and a location inside Naples’ most walkable downtown district has kept it a consistent presence on the water for a generation of Naples winter visitors.

Sailing under a catamaran’s twin hulls also gives passengers a notably steadier ride than a monohull sailboat in most conditions, a practical detail for guests who might otherwise worry about seasickness on their first time aboard a sailboat. That stability, paired with the boat’s open deck space, has made Sweet Liberty a common choice for guests who want the experience of sailing without the more pronounced heeling of a traditional keelboat.