From Toronto, there is a very convenient service, direct flights operated by Azores Airlines (previously known as SATA). The flight takes only about 5 hours, which is great when you are traveling with smaller family members who are anxious to get out and explore... the fellow passengers' patience limit.
The prices of the flight, accommodation, food, and drinks are more than reasonable! One thing I would recommend is to definitely rent a vehicle - even though the island is small, you will be able to see and experience more if you have a means of transportation.
As for the itinerary itself, we have decided to take it slow on the day of arrival and simply wandered through Ponta Delgada.
For the following 5 days, we have followed the absolutely excellent "Ultimate 5 Day Itinerary in São Miguel Island, the Azores" (link: https://www.theintrepidguide.com/sao-miguel-island-itinerary-azores-travel-guide/), and the remaining days we spent in Ponta Delgada minus "Swimming with Dolphins and Whale-Watching"...
A few tips:
- Rent a car! and don't take shortcuts through a gravel/mud road and check and doublecheck where GPS takes you. That is especially important during or after a rainy day!
- In Furnas, I would definitely recommend trying Cozido das Furnas in Terra Nostra Garden Hotel. The guide (link above) recommend a few other places, BUT... even though Terra Nostra Garden Hotel is only 2-3 EURO more expensive, the restaurant itself is by far better and it gives you free parking and free access to the Terra Nostra park and the thermal pool (8 EURO).
- Unless you are cooking yourself, it is highly recommended to book restaurants ahead of time. Even in slow season, the popular restaurants are filling in quick! In Ponta Delgada, I can recommend the following: A Tasca, Taberna Açor, Casa da Rosa and Armazéns Cogumbreiro (breakfast and light lunch). Try to work in a lunch Lagoa Azul when exploring Sete Cidades.
- If you see a thermal hot pool, stop, park and relax for an hour or two...
- ... and the most important tip: DON'T RUSH AND ENJOY THE ISLAND!