Designed as a larger sibling to the legendary Contessa 32, this 39-foot sailboat emerged from the drawing board of David Sadler in the 1980s, carrying forward the proven seaworthy characteristics that made the Contessa name synonymous with offshore capability. Built by Jeremy Rogers in the UK, the Contessa 39 represents a thoughtful evolution of the design philosophy that created one of sailing's most respected blue-water cruisers. While maintaining the robust construction and conservative design principles of her smaller sister, the 39 offers significantly more interior volume and comfort without sacrificing the seakindly motion that defines the Contessa lineage. Her moderate displacement hull and well-balanced sail plan make her equally suited for serious offshore passage-making and extended coastal cruising. The cockpit layout emphasizes safety and functionality, with high coamings and thoughtfully positioned winches. Below, the accommodation strikes a practical balance between comfort and seaworthiness, with sturdy joinery and sensible storage solutions throughout. Though fewer examples were built compared to the famous Contessa 32, those who sail the 39 consistently praise her solid feel, predictable handling, and confidence-inspiring behavior in challenging conditions, making her a worthy choice for serious cruising sailors.

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vs. Baltic 39, Dehler 38, Sabre 38 Mkii, Sweden Yachts 38, X 382