This is a rare opportunity to acquire a well-established, highly profitable seasonal sailing charter business located on the beautiful North Fork of Long Island. Operating only 4–5 months per year, this business offers an exceptional lifestyle with strong demand, excellent guest reviews, and a loyal repeat clientele.

The sale includes a classic 45’ sailing yacht (surveyed at $140,000) that serves as the centerpiece of the experience. The vessel is offshore-capable, beautifully maintained, and consistently praised by guests for its comfort, stability, and striking classic design. Its unique aesthetic and pedigree set this operation apart from other charters and contribute significantly to its brand identity.

This turnkey business includes all branding, website and domain, social media accounts, top-rated online profiles, booking software, operational checklists, customer lists, marketing assets, and well-established systems that make the business easy to run and efficient. The reputation is exceptional, supported by years of 5-star reviews across major platforms. Strong SEO and high visibility ensure repeat inquiries and consistent booking demand throughout the season.

The business operates with low overhead and does not require a storefront. Its profitability is driven by professional presentation, exceptional guest experience, and a highly efficient operating model. Demand during summer months regularly exceeds available sailing slots, leaving room for meaningful expansion for a new owner who wants to operate more frequently, extend the season, or add specialized offerings.

Growth opportunities include adding more daily sails, expanding into shoulder seasons, offering themed or premium experiences, developing partnerships with local wineries, hotels, and wedding venues, or hiring additional captains to increase weekly capacity. With strong regional tourism and consistent interest in boutique, small-group activities, the potential for increased revenue is significant.

The vessel is currently hauled for the winter, allowing for convenient out-of-water inspection. A full in-water sea trial will be available at spring launch. The timing gives a new owner several months to learn the business, become familiar with operations, and prepare for the upcoming season. Seller will provide transition support, including operating guidance, vendor introductions, and assistance with early-season planning.

This is an excellent opportunity for a USCG-licensed captain, couple, investor, or hospitality entrepreneur seeking a thriving, well-structured seasonal business with a strong brand and a remarkable vessel. Whether you wish to run the business personally, expand its offerings, or simply enjoy the lifestyle benefits of owning a premier sailing experience, this turnkey operation is positioned for continued success.

Financial details, equipment list, and business name will be provided to qualified buyers after a brief pre-screening and signed NDA.