Escape the ordinary with a luxurious private sunset cruise on Salem’s historic waters aboard When And If. Experience breathtaking views and memorable moments on this exclusive yacht adventure. Read on to learn what makes this trip a standout in Massachusetts’s maritime scene.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; minimal physical activity required
Wildlife
History
Salem's maritime history dates back to the 17th century, with its story of commerce, shipbuilding, and seafaring legends deeply intertwined with the local culture.
Conservation
The boat operators prioritize eco-friendly practices like waste reduction and marine safety to preserve Salem’s coastal environment.
Sunset Sail Salem
Escape the ordinary with a luxurious private sunset cruise on Salem’s historic waters aboard When And If. Experience breathtaking views and memorable moments on this exclusive yacht adventure. Read on to learn what makes this trip a standout in Massachusetts’s maritime scene.
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.
Arrive early for the best sunset views
Getting to the dock ahead of your scheduled departure ensures you can settle in and find the perfect spot for sunset photography.
Dress in layers for ocean breezes
Even during summer evenings, a light jacket or sweater can keep you comfortable as the temperature drops after sunset.
Bring your camera and binoculars
Capture the vibrant colors of the sunset and catch views of wildlife in the harbor area, like seabirds or occasional seals.
Confirm reservation and weather conditions
Weather can change quickly at sea; double-check your booking and be prepared for possible wind or light rain.
Layered clothing
Bringing layers helps you stay comfortable as temperatures shift after sunset.
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Sun protection
Sunscreen and sunglasses shield you from UV rays during the day and early evening.
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Camera or smartphone
Capture the stunning sunset and harbor views from the water.
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Binoculars
Use binoculars to observe seabirds or distant ships around the harbor.
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