My 2 cents….if you have the extra days ( vacation time is precious , I realize) I would do as Mal suggests and stay overnight in STT. silver is very unpredictable and very strict with bags and weights for flights.

We had our bags delayed from EIS-SJU and saw them two weeks later . It was a heck of a racket.

For comfort and less stress pay the little extra for a nice stay in STT and enjoy . Going on vacation shouldn’t be this stressful but unfortunately these last few years have been difficult.

Hoping you find a solution that works well for your situation…and most of all have fun