For all ages! • 2 Hour Charters • Perfect for the family!
Spend two hours gliding across the Chesapeake Bay as the sun drops behind marsh islands—this private catamaran charter from Oxford or St. Michaels, MD blends comfort, water toys, and a crew-ready experience for families and small groups. Add a bartender or bring the kids for SUPs and an unforgettable coastal sunset.
More ways to explore the area's outdoor wonders
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; guests should be able to step aboard and stand or sit on deck for the duration
Wildlife
History
St. Michaels and Oxford are historic Chesapeake ports with maritime roots dating to the colonial era and a longstanding skipjack and boat-building tradition.
Conservation
The Chesapeake Bay is a sensitive estuarine system—keep waste off the water, use reef-safe sunscreen, and follow crew guidance to minimize disturbance to birds and marshes.
Shore & Island Sailing Charters
For all ages! • 2 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.
Reserve the sunset slot early
Popular evening departures sell out—book your preferred date and add-ons at least two weeks ahead for summer weekends.
Bring layers and a light jacket
Temperatures fall quickly after sunset on the Bay—pack windproof layers and a warm midlayer.
Prepare for motion
If you’re prone to seasickness, take preventive medication before boarding and choose a seat near the center of the boat.
Protect your camera
Use a polarizing filter to reduce glare off the water and fasten straps to protect gear on a moving deck.
Light waterproof jacket
Wind and spray increase at sunset; a waterproof shell keeps you warm and dry.
spring
Polarizing sunglasses
Cuts surface glare and improves visibility for wildlife and sunset colors.
summer
Non-slip deck shoes
Soft-soled, grippy shoes make boarding and moving on deck safe.
Seasickness medication or wristbands
Useful for anyone prone to motion sickness, taken before boarding.