I hope that I may be able to offer some insight or advice for visiting the Azores. I have been there 7 times over the last 20 years, and when we go, we visit family and sight-see through the eyes of the locals. Santa Maria is our "home" island and the one I am most familiar with. It is low-key and has a rural atmosphere. It is the sunniest of the islands, hence its' nickname is "Ilha do Sol". It is very undeveloped (peaceful) and a very relaxing island, except during the "Mare de Agosto" music festival held annually in August. Christopher Columbus visited here on his return voyage of "discovering" the Americas. Santa Maria is a 15 minute flight away from Sao Miguel, but way less busy. It has the notable best beach in the Azores, Praia Formosa!
The island of Sao Miguel could keep you enchanted for a week, my top choices there are the Sete Cidades overlook (drive to the bottom where the stone bridge is and come up the other side of the lakes!), the village and Lagoa das Furnas (and the beach on the lake where they cook food in the dirt using only the volcanic heat), the tea plantation near Ribeira Grande (Cha Gorreana), from Ribeira Grande drive the old windy road to the Nordeste (not the new highway) where the miradours (scenic lookouts and flower gardens are), check out the different Logoas (lakes) on the island, and the town of Ponta Delgada itself is historical and beautiful. See the convent where the Santo Cristo statue is, visit the large marketplace in town, the pineapple plantation, the farm where tobacco is grown (located between Ponta Delgada and Vila Franca do Campo), the villages of Povoacao, Vila Franca do Campo, Rabo do Peixe... and Ribeira Grande are walkable and beautiful (10 minutes away are the caldeiras) . Plus there are numerous walking/hiking trails on Sao Miguel (actually, all the islands have them). If you like hiking or scenic walks, here is a good website www.trails.visitazores.com
The best beach in Sao Miguel is at Vila Franca do Campo, and there is also a water park there. A small ferry can take you to the small island (ilheu) which you can see from Vila Franca. .
All over the island you can walk the villages, frequent the shops and markets, relax at the countless outdoor cafes and the new port area, taste the different wines...and liquors made from pineapple and passion fruit (you can visit the factories as well)...the seafood, cheese and meats are splendid. The old buildings and churches are mostly dated from the 1500s and 1600s.
Terceira is a mix between Sao Miguel and Santa Maria...and a 1/2 hour flight away from Sao Miguel...I visited this island only once so I am not any expert there...what I saw I really liked! The town of Angra do Heroismo is fabulous!!
Study the flight times from www.sata.pt, the Azorean airline.. They fly non-stop from Boston all year and the flight time is just over 4 hours. SATA also code-shares with other airlines for year round travel from Canada and the rest of the United States. They also provide the inter-island flights. There is a summer inter-island ferry service available if you like slower travel. The best months to visit the Azores, weather speaking, are from April through November...of course June through August are the busy tourist season. The other months can be cool and rainy.
Peruse an Azorean guidebook or this link- www.azores.com for info on all the islands. Lots of videos on Youtube as well.
The other islands I have not mentioned are more out of the way, but I am sure just as special as the ones I really know.
If I can help in any way regarding visiting the Azores for a vacation, or you would like some genealogy guidance for your Azorean ancestry (I am always doing this when I am there), send me a Private Message.
FYI...An Azorean traffic jam is caused when the cows travel on the roads! I sure hope Rick pays a visit to these islands one day, there is so much he could add to his Portugal book for sure!