Booking Azores Airlines
I am not an AV geek like many in the miles and points space, so I have never been one to collect airlines. While many people reading this are probably in the other boat, it just was never me. Having said that, I am kind of excited about my trip next year after booking Azores Airlines. More so because I finally get to go to the Azores, a place high on my list for years, but the novelty of flying Azores Airlines is a nice additional spiff to the trip. After playing around with some Azores flights, dare I say it offers some value for flights to Europe? You do need to pay cash, but I think it could make sense for many people out there.
A Little About Azores Airlines
Azores Airlines is a small international airline based in the Azores Islands off the coast of Portugal. The headquarters are in Ponta Delgada, which is located on the island of São Miguel.
According to Wikipedia, Azores Airlines only has 10 planes in their fleet. The planes consist of Airbus A320-200 (3), Airbus A320neo (2), Airbus A321LR (3) and Airbus A321neo (2). They are set up more like domestic airplanes, so there is no lie flat set up on their long haul flights. That makes sense because their longest flights are about the same as flying cross country in the United States.
Currently the only airports in the US that Azores Airlines flies into is New York (JFK) and Boston (BOS). They also fly to North America cities of Montreal and Toronto. They have a decent little network throughout Europe too, which includes places like Lisbon, Barcelona (seasonal), Porto, London, Frankfurt, Paris (seasonal) and a few more destinations in Portugal.
The reason I ended up booking Azores Airlines is because they allow stopovers when planning their flights. This allowed me to book a couple of nights in the Azores, and a flight to Portugal after my stopover, all for the same price. That was too good of a deal for me to pass up, especially with a little deal stacking in the process.

My Azores Airlines Booking
I started my search out of Boston and New York to see which one offered better flight times and deals. I had hoped that Boston would have been the more viable option. That is because flights from Detroit to Boston are usually cheaper and easier to come by versus flying into JFK. I do also have the option to book into LGA and transit to JFK, but I hate doing that. Needless to say, I went into my trip planning with my fingers crossed that Boston would work out. It did not, since the price was a few hundred dollars more expensive versus flying out of New York. Sad trombone.
Working In A Stopover
Next I went to looking at various stop over options. I would be meeting up with some friends to celebrate a 50th birthday over a long weekend. I needed to land Friday morning and then would be ready to move on sometime Sunday. This was super easy to play around with on the Azores Airlines site using the multi-city booking option. I selected a flight out of JFK on Thursday night, landing Friday early, and then selected a flight out on Sunday. The flight out of the Azores will likely go to Lisbon, although Porto and some other destinations are options. You could then connect to other airports on Azores Airlines, or their interline agreement partners – like TAP Portugal.
After some searching, I knew that I could add a flight on Sunday to Lisbon without increasing the cost of the initial booking from JFK to Ponta Delgada (PDL). I decided to see how far I could push this though. I ended up trying some other airports in Europe to connect to from there, using Lisbon as a connection. In my searches this would usually would bump up the cost another couple hundred of dollars. There were some options that would keep the price about the same – like Frankfurt. I wanted to avoid Frankfurt if I could, because I loathe that airport. Even though it has some great options home to Detroit, or the East Coast of the US, I have been there enough that I wanted to skip it if I could.
Settling On Lisbon
I settled on just booking the flight to Lisbon and end it there after running a ton of searches. Even though I have yet to be able to find something good home from Lisbon, it is a good base of operations to build out something else if I need to. I have been tinkering with flying to Zurich for a few days, since I found a good award home using Aeroplan from there. I have plenty of time to figure that out though, and I just wanted to get my have of my itinerary locked in.

Stacking Deals For The Win
When it came time to book I was originally just going to book directly on the Azores website with my Capital One Venture X Business. I could then use points to wipe away the charge if I wanted to. This is something I do regularly, even if it isn't the best redemption option. That is when it dawned on me that my annual fee just posted and that meant I had a $300 travel credit to use. The problem was that I wasn't sure if Azores Airlines would show up on my searches. Even though I loathe travel portals, if it was possible to book my preferred routing then this would be a solid use for my credit.

Booking Via The Capital One Travel Portal
I was a little surprised that it was possible to book Azores Airlines via the Capital One travel portal. I could even build out a multi-city stopover and it priced out the same as on the Azores site. There was an additional small credit for a little over $30 on my account to use on top of the $300 credit too. This was from a flight booking I did last year with my yearly travel credit. The price dropped before the flight and Capital One proactively adjusted my booking which added the credit to my account.
My Cost Of Booking
All in all, my flight from New York to Ponta Delgada, with a two night stopover and then a flight to Lisbon, cost a little over $1000 in “business”. The flight in economy would have been around $300, and I could have booked it entirely with my travel credits. I decided to splurge since it was an overnight flight, and I needed to be able to hit the ground running with a group of friends meeting me there. Even though the business class looks to essentially be international premium economy, I felt like it was worth it for the extra comfort.
Booking Azores Airlines: ToP Thoughts
If you are interested in visiting the Azores, or just Portugal in general, then I think booking Azores Airlines should be on your radar. The prices, in economy especially, offer a fairly cheap gateway into Europe. Being able to add in a stopover in the Azores is just icing on the cake. There are even a couple of points hotel options in the Azores to book. The prices are pretty affordable points wise too. If you have some travel credits with your Venture X or Venture X Business then this could look even more enticing.
While calling Azores Airlines' business class business is generous, it should be comfortable enough. I flew something similar to Rio earlier this year in Delta Premium Economy, and I felt like it was fairly decent. There is a potential of Azores Airlines having to swap out plane types and me being stuck in a regular seat though, because of their limited fleet. Should that happen I will be arguing for a refund at the airport. From what I have read their call centers leave a lot to be desired if I waited until I got home. Have you ever flown Azores Airlines? Let me know over in the ToP Facebook Group.
