Spend eight private hours on a catamaran out of Oxford or St. Michaels, MD. Enjoy a fully crewed day with SUPs, a water hammock, fishing gear and optional catering for an all-ages celebration on the water.
Spend eight private hours on a catamaran out of Oxford or St. Michaels, MD. Enjoy a fully crewed day with SUPs, a water hammock, fishing gear and optional catering for an all-ages celebration on the water.
Verified experiences and guided adventures in the surrounding area.
Operated by Shore & Island Sailing Charters · Greenwich, New York
easy.
8 hours.
Minimal fitness required—able to step on and off a dinghy or ladder, swim optional.
Private day sails are available from Oxford or St. Michaels, MD; confirm your chosen meeting point at booking.
Yes—each charter includes a captain and mate who handle navigation, safety and provisioning.
SUPs, a Sun Chill water hammock and basic fishing gear are included with the charter.
Guests may BYOB; a professional bartender service is available as an add-on for a fee.
Yes—the catamaran has a day head for guest use during the charter.
This is an all-ages cruise; life jackets and safety briefings are standard for families.
St. Michaels and Oxford each have long maritime histories tied to shipbuilding and the Eastern Shore’s working waterfronts.
Use reef-safe sunscreen, avoid anchoring on submerged grasses and follow crew guidance to minimize wildlife disturbance.
Shore & Island Sailing Charters is based in Greenwich, New York and offers private catamaran charters that depart from Oxford or St. Michaels, MD. The company focuses on private, reservation-based experiences aboard catamarans for groups seeking a full day on the water or an evening sunset cruise. Shore & Island Sailing Charters lists two primary trips: the Private Full Day Sailing Catamaran Charter, which provides a personalized day on the water with coastal views and relaxed cruising, and the Private Sunset Sailing Catamaran Charter, which departs at sunset for an evening cruise as the sky turns vibrant. Each trip is described as a private charter, meaning the vessel is reserved exclusively for the booking party. Details about vessels, crew qualifications, safety protocols, and exact itineraries are provided at booking and may vary by departure port. Shore & Island Sailing Charters is featured on The Adventure Collective, where the business is presented alongside trip summaries and booking information. Prospective guests should review available departure locations (Oxford or St. Michaels, MD), trip durations, and booking terms before reserving. The business emphasizes private charters on catamarans and provides direct options for full-day and sunset experiences for those seeking an exclusive sailing outing.
Book with Shore & Island Sailing Charters