Hi, I'm traveling from NYC area. What were the flights like? How many stops, I imagine Boston is one of them. Do you have to go to Lisbon first?
I am not on this program but I looked at the websites www.kayak.com and www.skyscanner.com just to see what flights go from the NYC area to Horta. I see most transit thru Lisbon. I also see there is an offer of free airfare on Azores Airline from Boston currently on this program, so I see that is why you mentioned Boston.
You'd have to decide if the hassle of going thru Boston and flying Azores Airline would be worth it to you or if you would rather fly from JFK on Air France or from Newark on TAP (Portugal airline)/United (legacy airline).
IF you do decide to book your own airfare, be sure to book directly with the airline of choice and not a 3rd party online travel agency. They can give you routes that don't actually exist as well as jerk you around on fares.
If someone else books airfare for you, be sure they give you an adequate amount of transit time at your layovers. Just because an airport might say 45 minutes is "enough" time for a transfer does not mean I, as a senior, lol, can make it in that amount of time.