The Big Island
São Miguel is the largest of the Azorean islands, and as such there are a lot of things to see and do there. There are direct flights from Boston, New York, Providence, Toronto and Montréal to Ponta Delgada Airport, the main airport on São Miguel island.
If you are planning on visiting Sao Miguel, or any Azorean island for that matter, I highly recommend renting a car. There is a bus system available, but for sightseeing purposes the buses do not run frequently enough. As I mentioned in my introductory post, driving around the Azores is a blast. You get amazing views at every corner, and the roads are very well maintained.
There are major car rental companies like Sixt, Enterprise and Hertz, but I suggest renting from Ilha Verde instead. They were very professional, and have a more modern fleet of vehicles available. There are a few mixed reviews online, so we may have just lucked out. However, the car we got from Ilha Verde was objectively much nicer than the one we got from Sixt, with a cheaper price to boot. In April, rental prices were $20-$30 a day for a compact car. Expect prices to be much higher during the busy summer months.
One tip - if you are not an expert in driving stick shift, the Azores is certainly not the place to brush up your skills as there are too many mountainside roads. While an automatic car will cost a little more, it may be worth it for peace of mind.
Hotel vs Airbnb
If you want to use points for a free stay, unfortunately you are out of luck. There used to be a few nice SPG hotels, but since the merger of SPG into Marriott, it seems those hotels decided not to become Marriott properties. There are still lots of affordable hotels around, ranging from hostel accommodations to luxury resorts. However since our group consisted of four people, Airbnb was the cheaper option.
For the first part of the trip we stayed in the central part of the island in an Airbnb which cost only $30 per person per night. It was a truly local experience in a very small town with lots of dogs! The Airbnb even had a shared pool. but unfortunately the weather was not warm enough for us to use it.
For the last part of the trip we stayed closer the main city of Ponta Delgada at the pineapple house. Little did I know that the house would actually be on a pineapple plantation, which is cool enough in itself. Over the course of the trip we also learned that the Azores is famous for its uniquely flavored pineapple. Surprise, surprise, our Airbnb host was the owner of the plantation, so he gave us a private tour and some amazing homemade pineapple jam! I definitely recommend staying at this house if you visit São Miguel!
In general, every Airbnb host we interacted with was incredibly gracious. Each one provided us with local breakfast foods upon arrival, and everyone happily told us which sights to visit. You could easily tell that each host was proud of their home island, which I feel really added to our experience.
So despite this being a points-centric website, in the Azores, I would suggest staying at an Airbnb! If you use your Chase Sapphire Reserve, you will be able to get 4.5% of your cash back with Airbnb bookings since it counts as a travel purchase.
West, Center, East
São Miguel is relatively small, and you can drive from one side to the other side of the island in about four hours. Depending on where you are staying, however, there can still be a fair amount of day to day driving to see the sights. I suggest breaking up the island into three parts, and sticking to one part of the island per day.
Three to four days on São Miguel island should give you sufficient time to see most things. In the next three parts of this Azorean series, I will go into more detail about where to eat and what to see on the different parts of the island!