Discover the North Shore waters aboard the vintage sailboat When And If with Sunset Sail Salem. This private daysail offers personalized routes, stunning coastal views, and a chance to experience the sea in an intimate setting. Perfect for special occasions or a relaxing day on the water, it’s a highlight for any outdoor enthusiast in Salem.
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Difficulty
easy
Duration
2–4 hours
Fitness Level
Suitable for most fitness levels, with no prior sailing experience required
Wildlife
History
Salem’s maritime history dates back centuries, with sailing being a central part of its cultural identity since the colonial era.
Conservation
Sunset Sail Salem emphasizes environmentally responsible sailing practices, helping to preserve the coastal ecosystem for future generations.
Sunset Sail Salem
Discover the North Shore waters aboard the vintage sailboat When And If with Sunset Sail Salem. This private daysail offers personalized routes, stunning coastal views, and a chance to experience the sea in an intimate setting. Perfect for special occasions or a relaxing day on the water, it’s a highlight for any outdoor enthusiast in 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.
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.
Dress in layers
Weather at sea can change rapidly, so bring layered clothing to stay comfortable throughout the trip.
Bring sunscreen and sunglasses
Protection from the sun will make your sail more comfortable, especially during midday hours.
Secure loose items
Hold onto or stow away personal belongings to prevent them from falling overboard during the sail.
Arrive early
Getting to the harbor ahead of schedule ensures a relaxed start and plenty of time to enjoy your sail.
Layered clothing
Adjustable outfits ensure comfort despite changing weather conditions on the water.
spring|summer|fall|winter
Sunscreen
Protect your skin from strong UV rays while out on the open water.
summer
Sunglasses
Reduce glare from the water and enhance visibility during your sail.
summer
Binoculars
Great for spotting wildlife and appreciating distant coastal scenery.
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