When I saw a photo similar to the one above, of two picturesque lakes, I became obsessed with the nine islands that make up the Azores and would not rest until Nat said, “Let’s go!” There was something about the lush, sparsely inhabited landscapes that captured me. With short notice, our work schedules aligned and I had only a couple weeks to plan a two week trip to Lisbon and the Azores (an autonomous region of Portugal).
The Nine Azores Islands
Sao Miguel – largest, most populated, most visited, most to do
Santa Maria – warmest, best beach
Terceira – second most populated, unique caves
San Jorge – cheese, great surfing
Pico – highest peak in Portugal, whale watching
Faial – moon-like volcanic landscapes
Graciosa – less touristy, few “sights” to visit
Flores – western most island, hydrangeas
Corvo – smallest
Our Two Weeks in Lisbon and the Azores
Days 1-5: Lisbon city life
Days 6-9: Sao Miguel lakes, hikes, sunsets, hot springs
Day 10: Faial day-long layover, private tour of the island
Days 11-13: Terceira stay on nature preserve, caves
Days 14: Lisbon sad good-byes
How did we choose which islands to visit? It was so hard! Sao Miguel is a shoo-in. From there, it seems that first-time visitors should stick to Terceira, Pico, Faial, and San Jorge. These islands have the most “tourist attractions” and also have frequent flights. It is popular to visit Sao Miguel, Pico and San Jorge as the three are quite close. My advice is to go with your gut, or alternatively, go with the coolest accommodations!
What you should KNOW
People have sometimes said they were bored in the Azores, so let me say this: If you need nightlife, shopping, buzzing atmosphere and entertainment, then seek out a different trip. The Azores are wild, natural, quiet, and mostly untouched. You will find yourself relaxing, hiking, eating loads of fish and cheese, and driving. There is an expansive stillness to the Azores that you can settle into and explore at your own pace, and the views offered more than enough entertainment for us.
How did we GET THERE and GET AROUND
We chose to fly in and out of Lisbon (2.5 hr flight), spending time there on either end. If you are traveling from the U.S. you can fly from Boston (5 hr flight). This will save you time and money. Between the islands, we took short flights on SATA. The flights were not as affordable as one would expect so the airfare does add up. In warmer months, ferries are a more affordable option to commute between islands.
Note: The SATA airline that services the Azores can be a bit unpredictable, and sometimes flight times can change or be cancelled with little notice.
On Sao Miguel we rented a car. After reading numerous reports of scams, I did a detailed walk-through and took several photos of the car, so as not to be accused of any damage during drop-off. We had no issues with the rental, thankfully. If you need an automatic car, don’t delay in reserving one. On Terceira, our AirBnB came with a car for an additional cost. Lastly, during our one day on Faial, we hired a private tour for the day. You must rent a car in the Azores and you must be a comfortable driver – the roads are windy and, if weather conditions are poor, visibility can be tough.
Where did we STAY
AirBnB all the way! If you go into an Azores vacation expecting luxury, you will be disappointed. While yes, there are upscale rentals and beautiful homes, and even a suitable hotel or two, that is not really the true Azores experience. The only issue I had with AirBnB is they all had a 3-night minimum, which dashed plans on Sao Miguel of splitting time on the East / West side of the island. I found that hosts were not willing to make exceptions. If you are going with a group, the world is your oyster, as there are several larger homes that are simply jaw-dropping.
In Terceira our accommodation exceeded all of our expectations. Set on a wildlife preserve, down a steep hill and without any other home in sight, it was unlike any other place we had stayed before. A British couple had spared no expense in building the property, which was modern, austere, and included a glass-walled shower. If there wasn’t so much to explore on Terceira, we would have spent an entire day exploring the grounds of the property.
Before you BOOK…and TIPS
Pack smart. No one will care how you are dressed. We mostly wore outdoorsy or hiking clothing. Depending on the season, I’d make sure you have a good raincoat and a solid pair of hiking boots.
Check the webcams. The weather varies vastly from place to place on the island, especially on Sao Miguel. Most of the views, like Sete Cidades or Lagoa do Fogo, can be a complete bust if there is fog. Save yourself the drive, check the cameras, and head out to the clearest area! We kept our days flexible and on the foggiest day did Furnas.
Plan your days. This is especially important on Sao Miguel which requires more driving. Mark your map in advance to make the most of your time in different parts of the area. This also is important for meals – if you will be out late, be prepared and have food already purchased at home. As New Yorkers, the “city that never sleeps”, our first night we got caught out late, without dinner, and had a tough time finding food. Also on that note, make sure your phone is charged 🙂
Stay tuned for a run-down of our itinerary and how we spent our time in the Azores. Be sure to follow along on Instagram to see more photos, and check out our story highlight!
Hope this inspires you to get out, wherever you are.
– Nat and Riki
Nat + Riki 
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