Good for you - go!   Others have give such wonderful and specific
advice.   We went last year and stayed 5 weeks, visiting 5 islands.
We also spent a total of 3 days at the Archives and had wonderful
success in finding our records.    We don't speak Portuguese, but did
ok.    I have a trip description with photos on my blog.   Just click
on the label for Azores over on the right side-bar.  
http://marciaandalan.blogspot.com/

A great place to get specific information, and find a guide, is on the
Trip Advisor page for the Azores.  There is an extensive forum where
you can ask questions, plus there are a large number of lodging
reviews on this site.  I did the bulk of my planning using this site,
and got great information and hands-on help.
http://www.tripadvisor.com/Tourism-g189123-Azores-Vacations.html   I
posted several reviews when we came home on this site and encourage
others to do the same.

Another of my favorite Azores sites is the ExPat Island Guide that can
be found here http://www.expatislandguide.com/expat_set.htm    The
owner of the site, Roberto Santo Cristo Soares, is also a frequent
contributor on Trip Advisor's Azores forum and helped us a great deal
in planning and even making arrangements for our trip, particularly
while on San Miguel.

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