For all ages! • 8 Hour Charters • Perfect for the family!
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.
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Difficulty
easy
Duration
8 hours
Fitness Level
Minimal fitness required—able to step on and off a dinghy or ladder, swim optional.
Wildlife
History
St. Michaels and Oxford each have long maritime histories tied to shipbuilding and the Eastern Shore’s working waterfronts.
Conservation
Use reef-safe sunscreen, avoid anchoring on submerged grasses and follow crew guidance to minimize wildlife disturbance.
Shore & Island Sailing Charters
For all ages! • 8 Hour Charters • Perfect for the family!
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.
Location
Greenwich, NY
Business headquarters
Departure Ports
Oxford & St. Michaels, MD
Select your preferred marina
Private Charters
Exclusive
Private vessel for each booking
Trip Types
Full day & Sunset
Daytime and evening charters
Choose a full-day or sunset charter departing from Oxford or St. Michaels, MD — private bookings are available for groups and special occasions.
Book early for summer weekends
Summer weekend slots fill fast—reserve at least 4–6 weeks ahead to secure preferred dates and start locations.
Bring reef-safe sunscreen
The charter supplies shade and coolers but not reef-safe sunscreen—protect the water and your skin.
Pack layers and a waterproof bag
Sea breezes can be chilly; bring a wind layer and a dry bag for cameras and phones.
Let the crew know activity plans
Tell the captain if you want to fish, paddle or anchor for lunch so the crew can prepare gear and plan the route.
Reef-safe sunscreen
Protects skin and the local marine environment during long sun exposure.
summer
Waterproof phone case/dry bag
Keeps electronics and valuables dry when swimming or on the bow.
Non-marking deck shoes
Protects the boat’s deck and provides traction when moving about.
Light wind jacket
Blocks sea breeze on open-water stretches and cooler mornings.
spring