I love the hand-painted faces and brass buttoned blue jackets on these vintage wooden sea captain nesting dolls--plus the short white pant legs and black boots peeking out below those jackets, and the pipes in the corners of the mouths of the largest two! From what I've found, these sea captains are among the most collectible of all nesting dolls, and justifiably so I think as they're pretty charming!
I'd guess these date from the 1960s. I believe there were originally five of them and that it is the second largest that is missing. The largest measures 6 1/2" tall x 2 5/8" wide. Following, in sequence, they measure: 3" tall, 2 1/4" tall and 3/4" tall. The smallest, which fits inside all of the others, is solid wood (does not open). The jacket of the largest is a lighter blue than the rest, but based on others I have found is original to this set. They are in good overall condition, with what appears to be some peeling to their varnish/coating--as documented in detailed photos.