Best airline option from Boston to the Azores?

TAP does not fly from Boston to the Azores. They might be selling tickets as a code-share partner with Azores Airlines, which is the only airline that does fly nonstop from Boston to either Terceira (Lajes) or Sao Miguel (Ponta Delgada).

At the top of this Portugal is a post, Azores Travel Advice, written by the webmaster. You will find a link that will bring you to my Azores guidebook. You should read the first 52 pages, which are totally free to access. In these pages will be all the information you need regarding flying to, and among, all the Azores islands.

Good advice above from Carl. BTW his guidebook is excellent and anyone even thinking about a trip to the Azores should get his guidebook and study it before they do anything else.

I've flown both TAP (to/from the Azores from Lisbon) and SATA/Azores Airlines (within the islands). If you're flying inter-island, you have no choice, you're on SATA (though sometimes code-shared with TAP). Both airlines are perfectly fine, though fairly basic and utilitarian. Weather-related delays in the Azores are not unusual, so don't plan any critical connections expecting Swiss-watch precision, that's not how things work there.

That said: United now has seasonal service from Newark (EWR) to the Azores, but that won't be going in February. Which raises a question: hopefully you are not going to the Azores expecting a warm, tropical beach experience in February. It won't be snowy and freezing, but it won't be "swimming weather" for anyone but the most dedicated crazies. The Azores is not really a "beach" destination any month of the year, and it's highly unlikely you will want to get in the water there in February (unless you do the Polar Bear Club plunge thing on January 1). If you're looking for a warm sun and swimming vacation in February, you might want to look elsewhere.

I have to keep my comments brief, but I would not recommend the Azores in February, I would say it’s probably the worst month to go weatherwise.. The weather can get iffy and it can affect flights due to high winds. Save that trip for April vacation. Azores Airlines is basically your only option. The previous responder was correct that that the flight through TAP is code sharing with Azores airlines. I fly to the Azores a few times a year and the airline has improved greatly in the last handful of years. The issues that Azores airlines has are during the high summer season.

Thanks everyone for your thoughtful replies, I really appreciate it! Thanks for the clarification on the codesharing with SATA/TAP.

My challenge is that we’re limited to the school holidays and my teenager is already doing a school trip over April break. I would book this trip to the Azores for April in a hot minute if it was an option! I’m not so concerned about the weather there in February, being from New England, it will still be warmer and rain is ok. I am worried about flight delays and/or flights being affected by weather as we are working within the school calendar and my teenager is prone is airsickness.

Definitely love everything I’m seeing about the Azores and will definitely visit, even if it’s not this time!

Expect rain. Probably more than a little.

The Azores may be the wettest place I've ever been (and I live in Seattle). If it's not actively raining, it's humid enough that it might as well be. And some actual rain will come along soon enough.

That was my impression from being there in the summer. February? Yes, it'll be less wintery than New England, but don't expect much warmth.

My wife and I are headed to Sao Miguel in 2 weeks. Our last visit, we flew into Terceira and took a puddle jumper to visit Sao Miguel. Our last trip was also in January, and being from New England, we thought the weather was great! Sure it rains frequently, but much like New England "if you don't like the weather, just wait a minute and it will change" , is also true of the Azores. We also appreciate that the direct flight out of Boston has you there in just 4 1/2 hours. Additionally, the scenery is stunning, the people are very friendly, The food is wonderful and it's surprisingly affordable.