September 6th, 2026
Step aboard the 131ft Harvey Gamage for a front-row view of Gloucester’s Parade of Sail and the Mayor’s Cup Race. Feel the wind, learn from the crew, and witness classic schooners pass the Fishermen’s Memorial for a day of maritime heritage on the water.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
4–6 hours
Fitness Level
Light to moderate fitness; able to climb a few companionways and stand for extended periods on a moving deck.
Wildlife
History
The festival honors Gloucester’s long maritime and boatbuilding heritage and the sailing industry that helped build America’s coastal economy.
Conservation
Visitors are encouraged to minimize waste, respect marine wildlife, and follow local regulations; operators typically brief passengers on responsible behavior around protected areas.
Sunset Sail Salem
September 6th, 2026
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
Wind off the harbor is cooler than on land; bring a warm mid-layer and a waterproof shell to stay comfortable during the long parade and race.
Non-marking deck shoes
Wear shoes with good traction and non-marking soles to move safely on wet wooden decks.
Plan for seasickness
If you get queasy, take preventative medication before boarding and sit midship where motion is least noticeable.
Arrive early for boarding
Boarding begins at 9:00am; arriving on time ensures you get a preferred vantage and time to stow gear and get oriented.
Waterproof jacket
Protects against spray and coastal gusts during the parade and race.
fall
Non-marking deck shoes
Provide traction on wet wooden surfaces and protect the boat’s finish.
Sunscreen and sunglasses
Bright sun reflects off the water; protect skin and eyes during long viewing periods.
summer
Camera with extra battery
Capture sail profiles and action shots of the fleet and Fishermen’s Memorial.