Planning a trip to the Azores is daunting, especially in off season when islands are less easily accessible, and picking which islands to go to and how to get there takes time.
It wasn’t hard to get to Sao Miguel, with direct daily flights to Ponta Delgada from Boston, and it was quick and inexpensive. It’s a red-eye flight, so arriving at sunrise meant booking a hostel was tricky. I managed to check into Bruma Hostel at 8 am, and got to shower and have breakfast before snuggling into bed for a day nap.
I met up with a couchsurfer from Lisbon at a taberna for some 80 cent beer and bifana, then he drove us to Lago do Fogo for a picture perfect view. We watched the sunset at the western point of the island, Ferraria and then taberna hopped our way back to Ponta Delgada. I was always the only woman inside, a smokey and dodgy lit space, so I preferred the outdoors and Nordeste much more. My favourite places in Sao Miguel were Cete Cidades and Furnas Lake, especially bathing in the nearby geothermal springs, Poca da Bona Beija.
I then visited the triangle islands – Faial, Pico and Sao Jorge, each for only a couple of days or nights. I flew to Horta, Faial and couchsurfed there with an Italian who had the flu (a sensitive time to be close to anyone sick) but a gorgeous view over Pico island. The first 2 days I barely even saw the island, but the last day I could see the entire mountain, all the way to its peak.
Faial had some dramatic landscapes on the west end, where Capelinhos volcano erupted from 1957 to 58. Horta was the most charming town, with art and cafe culture thriving among the charming facades, and houses being rebuilt and refurbished all around.
When I went to Pico, I only hiked up until the Casa de Montanha visitor center, since everything higher up than that was fogged out. I tried some local wine from the wine co-op in Madalena.
Sao Jorge was my personal favourite, at least for the outdoors. The hiking, dramatic sea-cliffs and fajas made you want to stay outside all day. I rented a scooter, since a car would keep me too much inside, and drove some of the crazy roads from the coast to the cliffs and across the island. The deserted lighthouse Ponta dos Rosais on the north tip was creepy, but the whale lookout and Sete Fontes forest nearby were worth visiting. Sao Jorge is the king of place you can hitchhike a taxi, and a man still plows his field with rope, steel and oxen.
Terceira was a brief 1 day and 2 night stop. I slept at Hostel de Palmeira, quite likely the best hostel I’ve ever seen, in Praia da Vitoria, and had an entire 8-bed dorm and sea-view balcony to myself. In the morning I ran on the black sand beach, and it was always warm enough, even in the rain.
I rented a car from the Lajes airport on Terceira to get to Angra do Heroismo, considered by some to be the first city of the Atlantic. Its an historical place, beautifully located and has a beach in the city center. It had great restaurants, Tasca das Tias especially for steak, and I tried sea barnacles for the first time at O Pirata.
There were a lot of other mentionable things I did there in 10 days, and a lot more things I didn’t get the chance to do. Ideally, plan to go there for 2 or 3 months and simply go to every island, for a week each, and then you wont have to worry about planning in advance. I definitely plan on returning, specifically to see Corvo and Flores, and hope to see a whale next time.