Sunset sails, private charters, and day sails aboard the Margaret Ann, Tamerlane, and Schooner Serenity.
Choose from two-hour sunset sails, private vintage-boat charters, and relaxed day sails on Lake Michigan.
boat-charters · Douglas
Enjoy a private afternoon sailing on Lake Michigan aboard the Schooner Serenity near Douglas, Michigan. Relax or get involved with sailing in a peaceful, scenic setting perfect for families and friends.
Sailing S.H. & Saugatuck operates from South Haven, Michigan and offers curated sailing experiences on Lake Michigan. The operation features multiple vessels: the 37-foot Margaret Ann, the classic 1960s wooden Tamerlane, and the Schooner Serenity. Trip options include two-hour Margaret Ann sails at dawn or sunset, private charters aboard Tamerlane for up to six guests, and afternoon day sails on the Schooner Serenity.
Each experience highlights scenic cruising, relaxed on-deck time, and optional passenger participation with the crew. The Margaret Ann trips provide short, scenic escapes ideal for romantic evenings, sunlit afternoons, or early-morning sails. Tamerlane private charters offer an intimate vintage-boat setting for small groups who want a personalized outing. The Schooner Serenity day sail delivers a leisurely afternoon option that pairs well with dining in nearby Saugatuck or Douglas.
Sailing S.H. & Saugatuck lists specific trip durations and vessel details at booking so guests select the right experience. Crew members attend every sailing to manage the vessel and assist passengers. Basic safety procedures are followed during all excursions.
Visitors choose Sailing S.H. & Saugatuck for the variety of boats, straightforward booking for private and shared sails, and the scenic Lake Michigan itineraries departing from South Haven. The business provides authentic on-the-water experiences for both local residents and visiting travelers. Reservations are required to confirm vessel selection and time. Schedules vary by trip; prospective guests should consult the business's booking information for available dates and departure times. Departure and return occur directly at the South Haven harbor meeting point.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Departures from South Haven harbor
Historic and modern sailing vessels
Small-group private outings available
Short scenic evening escapes
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sailing S.H. & Saugatuck listing.
Sailing S.H. & Saugatuck offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Select a Sunset Sail, Private Charter, or Day Sail — check availability and secure the preferred vessel.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.