The demand for a unique Sam Nigro "Glostoar" is pretty steep...and although he does donate most of his oars to businesses and non-profits, coaxing him to paint an oar is sometimes possible.   
Custom oars take time and Sam strives to make each oar special for those on the receiving end.
Sending a text to:  617-875-6183  and describing what type of "Glostoar" painting you are looking for.. ie...your home...your boat...your pet...a gift for a loved one...etc.. is a good first step.  Being direct, polite and detailed works pretty good.  Sam is a boomer that loves tech--but the fingers are best suited for painting and fishing....so you may get no response, or a strange response.. It's recommended that you keep trying with niceness and praise...and you most likely will succeed.   Sam is on Facebook as well.  Providing detailed photos of the subject you are interested in will follow.. if the project is accepted.   Some info about what you want the oar to capture will be needed.  It is preferred that you stop by his Fisherman Way, Gloucester property and pick out the oar...or a sizing helps by text photos.  Sam wants the oars he presents to be done with meaning and love...so it really is a process...but a pleasant one.   Sam has dozens, I mean a "shipload" of oars to choose from "in stock" (while you and I are sleeping he is visiting his friends at Todd Farm and beyond..he gets em all). 
  This is an art lover, legend, supporter and provider entering his   "finest work era"... the "jury" status will be the publics choice.   
Thanks for your interest.