Much easier to get to Aruba from here. Bermuda is even easier, just about an hour and a half by plane.
That is one of the nice things about Bermuda & Aruba. Direct jet service from the US airports. Plus you go through customs there instead of Boston, JFK, etc.
I hate flying through San Juan. It is always am issue.
You take turbo props to most of the smaller islands because their runways are too short for jets. I remember getting all buckled in and then they canceled our flight and bumped everyone back to the flight an hour later.
My 2 year old son had a complete meltdown in the terminal. I pointed this fact out to the lady at the American Airlines counter that yes that was my toddler over the screaming on the floor. Please make sure we are on the next flight out. We found out from the pilot that they bumped us all because there were only 14 people on the plane. Therefore, we could ALL fit onto the next flight and they could save the fuel to fly there and back. Apparently, he said they do it all the time.
When we went to Hawaii we stayed on Oahu for two nights and then flew to Kona on the Big Island. It took an hour to go through TSA security at the Honolulu airport. The problem is they have too many flights through that airport. It was a huge pain for a 45 minute flight. I think the real problem was they did not have enough TSA screeners.