Sail the Chesapeake Aboard Schooner Windsong

Schooner Windsong — Cape Charles Sailing on the Chesapeake Bay

Schooner Windsong LLC operates out of Cape Charles, Virginia, offering a selection of schooner cruises and private charters on the Chesapeake Bay. Key trips include the Cape Charles Sunset Sail, Cape Charles Daysail, Cape Charles 4th of July Fireworks Cruise, and a Full Day Charter with options for swimming and paddleboarding.

Why choose Schooner Windsong in Cape Charles?

• Authentic schooner experience: Cruises take place aboard the traditional Schooner Windsong, a classic sailing vessel suited to leisure sails on the Chesapeake Bay.
• Variety of trips: Public sails and private charters provide options for short experiences or extended full-day adventures.
• On-water activities: Full-day charters can include swimming and paddleboarding; box lunches from local restaurants are available for charters.
• Special events: The Cape Charles 4th of July Fireworks Cruise pairs a sunset sail with waterfront fireworks viewing; guests may bring food and drinks for onboard enjoyment.

Featured trips

Cape Charles Sunset Sail

A scenic sunset sail departing from Cape Charles, offering views of the Chesapeake Bay at dusk. This option is designed for passengers seeking a relaxed evening on the water.

Cape Charles Daysail

A daytime sailing experience on the Chesapeake Bay that showcases coastal scenery and sailing time aboard a traditional schooner.

Cape Charles 4th of July Fireworks Cruise

Experience a sunset sail followed by a fireworks display viewed from the water. Guests are encouraged to bring favorite foods and beverages to enjoy aboard the schooner.

Full Day Charter

Customize a full-day Chesapeake Bay charter aboard Schooner Windsong. Options include swimming and paddleboarding and catered box lunches from local Cape Charles restaurants, making it suitable for groups, friends, and family outings.

Practical information and booking

• Location: Cape Charles, Virginia — sails operate on the Chesapeake Bay.
• Trip types: Sunset, Daysail, Fireworks Cruise, and Custom Full-Day Charters.
• Charter options: Swimming, paddleboarding, and local box lunches for full-day charters.

For exact schedules, availability, safety guidelines, guest capacity, and booking details, contact Schooner Windsong LLC directly. Booking policies, seasonal schedules, and weather-related updates may affect trip dates and departure times.

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Booking a sail with Schooner Windsong connects passengers to a traditional schooner sailing experience in Cape Charles on the Chesapeake Bay. Prospective guests seeking sunset views, daytime sails, fireworks viewing from the water, or a customizable full-day charter will find clear trip options and on-water activities available through the operator.