Have you read InterCaribbean’s baggage policy? It looks like they have a 10lb. limit on carry-ons, so you most likely will need to check bags. They also say their lowest fares don’t include free checked bags. We have found Seaborne’s baggage policies suit us better.

And, yes, weekends at SJU can be crazy, not only because of cruise ships, but also Puerto Rican’s who travel home. Tuesday, Wednesday and Thursday are your best bet.

Which search engines are you using for fares, when are you searching and have you cleared your cookies? I have the best luck using ITA Matrix early on Tuesday morning. Maybe you need to get creative and fly Spirit to STT and charter a plane from there.