SanFranJanet is right. There is no painless route. I agree that SFO to Miami and then Miami to MoBay is the best bet. I did that flight twice and it was a piece of cake compared to the stop over at Atlanta and Charlotte. Miami is close to Jamaica so that flight is really short. We always take the red eye. I'm able to sleep on a plane but Markus isn't. It's never really comfortable but it's cheaper...
Markus prefers a stop over in Atlanta because it has a smoking room but that room is like a gas chamber. Enter at your own risk.
The flight to Jamaica from San Francisco is really a drag. It's all worth it though the minute you arrive.![]()