Herreshoff 50 Sailboats for Sale & Market Overview

The Herreshoff 50, primarily recognized in the modern cruising community as the Herreshoff Caribbean 50, represents a bridge between the legendary racing heritage of the Herreshoff Manufacturing Company and the late-20th-century era of blue-water fiberglass yachting. Designed by Halsey Herreshoff—grandson of the prolific Nathanael G. Herreshoff—this model was conceptualized as a sea-kindly, long-range ketch capable of handling the heavy trades of the Caribbean and the rigors of ocean crossings. While the "50" designation has been used historically for the New York 50 (NYYC 50) racing class of 1913, the production model most commonly encountered today is the 50-foot ketch built largely by D. Cheng Boat Builders in Hong Kong and other semi-custom yards during the 1970s and 80s. These vessels were often constructed with input from innovators like Garry Hoyt, aiming to combine a traditional aesthetic with a versatile centerboard configuration that allowed for both deep-water stability and shoal-draft exploration.