Chrysler 20 Sailboats for Sale

Hull Type

Monohull · wing

Rig

Masthead Sloop

LOA

20' · 6.1 m

Disp.

2,200 lbs · 998 kg

First year

1977

The Chrysler 20 was introduced in the mid1970s as a compact, trailerable response to the growing demand for "pocket cruisers" that could be easily managed by a small family or a solo sailor. Designed by the esteemed naval architect Halsey Herreshoff, the boat was intended to bridge the gap between Chrysler’s smaller daysailers, like the Mutineer 15, and the larger, more substantial Chrysler 22 and 26 models. Despite its shorter overall length, the Chrysler 20 retains the distinctive Herreshoff aesthetic—functional, sturdy, and surprisingly stiff under sail. It remains a popular choice for sailors who prioritize ease of launching and retrieving without sacrificing the security of a ballasted keel and a weathertight cabin.