Discover the peaceful charm of Salem Harbor with a private 2-hour Day Sail aboard 'When And If.' Perfect for history lovers, nature fans, and anyone wanting a relaxing escape on the water, this experience offers stunning views and personalized service. Keep reading to find out more about this unique sailing adventure!
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; minimal physical exertion required.
Wildlife
History
Salem's maritime history dates back to the 17th century, making its harbor a historic hub for explorers and sailors alike.
Conservation
Sunset Sail Salem emphasizes eco-friendly practices by minimizing waste and respecting local marine ecosystems during sails.
Sunset Sail Salem
Discover the peaceful charm of Salem Harbor with a private 2-hour Day Sail aboard 'When And If.' Perfect for history lovers, nature fans, and anyone wanting a relaxing escape on the water, this experience offers stunning views and personalized service. Keep reading to find out more about this unique sailing adventure!
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.
Location
Salem, MA
Sails on Salem Sound
Classic Yachts
Malabar X & When And If
Two crewed, historic vessels
Award Winner
Malabar X
Recognized winner in its class
Tours Offered
11
Private and public sails
Book a private charter or join a 2-hour day or sunset sail aboard Malabar X or When And If — secure preferred dates now.
Wear weather-appropriate clothing
Sailing sessions can be cool and windy, so dress in layers and bring a light jacket.
Bring your camera
The scenic views of Salem Harbor and surrounding coastline make for fantastic photo opportunities.
Arrive early
Arriving 15 minutes beforehand ensures a relaxed boarding experience and time to enjoy the harbor views.
Prepare for variable weather
Check the forecast and consider bringing sunscreen or hats for sun protection.
Light waterproof jacket
Protection against wind and splashes on the water helps keep you comfortable throughout the sail.
spring|summer|fall|winter
Sunscreen
Shield your skin from UV rays during sunny sailing days for added sun protection.
summer|spring
Sunglasses
Reducing glare from the water enhances visibility and comfort during your trip.
summer|spring
Hat or cap
Provides shade and helps protect your face from the sun while sailing.
summer|spring