The Windrose 5.5 is an American trailerable sailboat that was designed by W. Shad Turner as a pocket cruiser and first built in 1977.

The hull has a raked stem, a plumb transom, a transom-hung rudder controlled by a tiller and a fixed fin shoal-draft keel.

[1][4] The design has sleeping accommodation for four people, with a double "V"-berth in the bow cabin and two quarter berths under the cockpit.

"[3] In a 2010 review Steve Henkel wrote, "by 1980 the design trend was toward wider boats, for extra stability as well as cabin space.

Principal among these were (a) eliminating the potentially troublesome steel centerboard and substituting instead a shallow iron-filled keel, and (b) rearranging the cabin space for more elbow room.