Sail Salem: Private Charters & Sunset Cruises on Salem Sound
Experience classic yachts, award-winning sailing, and customizable private charters from Salem, Massachusetts.
Featured Sails & Charters
Private charters, 2-hour day and sunset sails, and seasonal festival voyages aboard Malabar X and When And If.
About Sunset Sail Salem
Sunset Sail Salem is a Salem, Massachusetts sailing operator offering a curated collection of private charters, two-hour public sails, and special-event voyages on classic yachts.
The fleet centers on two notable vessels: the award-winning schooner Malabar X and the classic yacht When And If. Trips include private charter daysails and sunset sails on both yachts, public 2-hour sunset and day sails, and seasonal trips such as the Gloucester Schooner Festival. Specific themed sails include Morning Mimosa Sail and G&T Tuesday Sail, plus options that let guests customize route and experience.
Private charters provide an exclusive experience where a captain and crew manage navigation and onboard service while guests relax or participate at their discretion. The When And If accommodates larger gatherings — noted for hosting up to 32 guests — and is frequently used for sunset charters and private events. The Malabar X is highlighted for its competitive recognition as an award-winning schooner and for its role in festival and race events.
Public two-hour sails feature scenic passage along Salem Sound, with sunset cruises emphasizing coastal views and onboard storytelling from seasoned crew members. Morning and themed sails add beverage-focused hospitality and light participation opportunities.
Sunset Sail Salem positions itself as a third-party provider of memorable on-water experiences in the North Shore region, focused on classic vessels, customizable private charters, and public sails that showcase Salem Sound and nearby coastal landmarks.
Reserve a Classic Salem Sail Today
Book a private charter or join a 2-hour day or sunset sail aboard Malabar X or When And If — secure preferred dates now.