Delta flies to Ponta Delgada from New York-JFK in the summer. Azores Airlines (aka SATA regionally) flies from Boston and Toronto year-round. Tip: A cheap flight from Minneapolis to Boston on JetBlue (also sold on azoresairlines.pt) may open up more options.
Inter-island flights: Up to $100 one-way on SATA. Be flexible in case of cancellations; try to book connecting flights on the same ticket. If you are flying to or from mainland Portugal, SATA will route you to or from another island within 24 hours for free (see encaminhamentos.sata.pt).
Stopovers: Azores Airlines offers a free stopover for up to seven days on the way to Lisbon, Porto and other destinations (stopover.azoresairlines.pt).
Packages: Many trips (and travel inspiration) are available at azoresadventures.com and azores.com.
Where to stay
Casa da Lomba: Villas in Mosteiros, São Miguel. 011-351-910-934-815; booking.com.
Quinta da Meia Eira: Ecolodge in Castelo Branco, Faial. 011-351-965-435-925; meiaeira.com.
Azoris Angra Garden: Hotel in Angra do Heroismo, Terceira. 011-351-295-206-600; azorishotels.com.