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Easy Sailing • Sleeps 4 • Perfect for Bay Adventures Set sail on a well-kept and seaworthy 1990 O’Day 272 — an ideal cruiser for couples, small families, or solo sailors looking to explore the Bay in comfort and confidence. This boat is thoughtfully rigged for solo sailing, making it easy to handle whether you’re an experienced sailor or a confident beginner. Despite being easy to manage alone, it comfortably sleeps up to 4 people, making it perfect for overnight trips, relaxed weekends on the water, or a unique getaway experience. Features: - Built in 1990 – solid, proven design - Well-maintained & seaworthy - Rigged for solo sailing – simple, efficient sail handling - Sleeps 4 comfortably - Cozy interior with space to relax, eat, and unwind - Great balance of performance and comfort - Perfect for day sails, weekend cruising, or learning the ropes Whether you’re looking for a peaceful solo sail, a romantic sunset cruise, or a fun weekend escape with friends, this boat delivers a smooth, reliable sailing experience in a classic cruiser that’s easy to love. Sailing lessons are available as well as full charters. Captain available on request: $200/hour
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You’ll get helpful information for your departure after your booking is confirmed.
Street Address For Arrival
Departure Location
Free cancellation up to 5 days before your trip.
Important Policies & Booking Notes Weather Cancellations: Safety comes first. If conditions are unsafe (high winds, storms, small craft advisories), the trip may be rescheduled or refunded at the owner’s discretion. Light wind, fog, or overcast weather are normal Bay conditions and not grounds for cancellation. Late / No-Show Policy: Late arrivals do not extend the rental period. No-shows or cancellations within 5 days of departure are non-refundable. Safety Requirements: All passengers must follow safety instructions and local boating laws. Life jackets are provided and required for children and non-swimmers. No operation under the influence of drugs or alcohol. Bareboat Requirements: This is a bareboat rental unless a captain is arranged in advance. Renters must demonstrate basic sailing competency and safety knowledge before departure. A brief checkout may be required. Boat Rules: - No smoking on board - No illegal substances - Pets are ok with me - Shoes off in cabin - Respect the boat and equipment - Any damage beyond normal wear may be charged to the renter - Portapottty head Misuse/overfill fee: $150–$250 if instructions are ignored or damage the unit. Return Condition: Boat must be returned on time and in the same general condition as departure. Excessive mess, lost gear, or damage may result in additional fees. Overnights (if applicable): Overnight stays must be approved in advance. Quiet hours at marinas must be respected. Captain available on request: $200/hour