Set sail into maritime history at Gloucester Schooner Festival, where tall ships and old-world sailing come alive with energy and tradition. Discover what makes this coastal event a must-see for adventure-seekers and history lovers alike.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
Full day festival events
Fitness Level
Suitable for most visitors, no special fitness required
Wildlife
History
Gloucester is known as America's oldest fishing port, dating back to 1623, and has a long-standing tradition of maritime craftsmanship.
Conservation
Efforts are ongoing to preserve Gloucester’s natural harbor and promote sustainable fishing practices to protect local ecosystems.
Sunset Sail Salem
Set sail into maritime history at Gloucester Schooner Festival, where tall ships and old-world sailing come alive with energy and tradition. Discover what makes this coastal event a must-see for adventure-seekers and history lovers alike.
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 views
Get to the waterfront early to secure a good spot for watching the sailing races and dockside activities.
Bring layers and sun protection
The seaside can be unpredictable—dress in layers and wear sunscreen for a comfortable day outdoors.
Watch the wind conditions
Sailing is wind-dependent, so check weather forecasts and be prepared for changing conditions.
Participate in dockside tours
Join guided tours of the schooners to learn about their history and their crews' skills.
Binoculars
Great for viewing distant ships and details up close during the parade.
Sunscreen
Protect your skin while enjoying full sun exposure on the waterfront.
Hat and sunglasses
Shield yourself from the sun and glare during outdoor activities.
Comfortable walking shoes
Explore dock areas and town sites comfortably.