Set sail on a captivating evening cruise with live Americana, roots, and country music aboard the Ardelle at Headlands. Experience breathtaking sunsets paired with talented musicians in a maritime setting.
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More ways to explore the area's outdoor wonders
Wildlife
History
The area has a maritime history dating back to the 19th century, known for its shipping and fishing communities.
Conservation
Maritime Heritage Charters is committed to eco-friendly practices, minimizing impact through responsible boating and waste reduction.
Maritime Heritage Charters
Set sail on a captivating evening cruise with live Americana, roots, and country music aboard the Ardelle at Headlands. Experience breathtaking sunsets paired with talented musicians in a maritime setting.
Maritime Heritage Charters operates heritage schooner sails and private charters based in Gloucester, Massachusetts. The company maintains and sails two traditional vessels, the historic 58’ fishing vessel Ardelle and the six-passenger Isabella, offering public sails and tailored private experiences across Gloucester harbor and the Essex River. Maritime Heritage Charters presents a seasonal schedule of festival sails, sunset cruises, music evenings, and quiet restorative voyages that showcase Cape Ann’s maritime history and coastal scenery.
Each voyage emphasizes authentic sailing, safety, and local knowledge. Public offerings include Gloucester Schooner Festival events such as the Parade of Sails, Parade of Sail, Greet the Fleet, and front-row Fireworks and Festival cruises; themed sunset music sails and the Silent Sail; as well as competitive Schooner Challenge participation with Maritime Gloucester apprentice cadets. Private charters provide customizable options for small groups, romantic evenings, family celebrations, and weekend or weekday hires with full crew service.
Maritime Heritage Charters partners with local musicians and Cape Ann artists for special-event programming and hires trained captains and crew to operate all sails. The business highlights small-group intimacy aboard Isabella and the historic character and capacity of the Ardelle for larger private bookings. Guests are encouraged to book early during the May–September season when festival and private dates are in highest demand. All descriptions reflect current published trip offerings and vessel details. Bookings typically include an experienced captain, crew assistance, and narrated local history that highlights Gloucester's fishing heritage and schooner traditions during each scheduled sail. Reservations are available online today.
Tours Offered
10 distinct sails
Festival, sunset, and private options
Vessels
Ardelle & Isabella
Historic 58' Ardelle and six-passenger Isabella
Season
May–September
Peak months for scheduled sails
Capacity
Private & public
Group sails and six-passenger private
Secure front-row festival views, sunset music sails, or an intimate private charter aboard Ardelle or Isabella—book early for May–September dates.
Arrive early to secure good viewing spots
Get there at least 15 minutes before departure to find a comfortable spot with the best sunset views.
Dress in layers for changing weather
Evening breezes can get cool—bring layers to stay comfortable during the cruise.
Bring a camera for scenic sunset shots
Capture the vibrant hues and scenic water views that make this sail truly special.
Limit alcohol consumption to stay alert and enjoy the music
Moderation ensures you fully enjoy the live performances and beautiful surroundings.
Sunscreen
Protect your skin from UV rays during the outdoor sail.
summer
Binoculars
Enhance your view of distant ships or wildlife in the water.
Foldable chair or blanket
Bring comfortable seating for relaxing during the performance.
spring; summer; fall; winter
Windbreaker or light jacket
Stay warm against breezes that pick up in the evening.
spring; fall; winter