SXM connecting flight strategies?

Bart -my real name-

Senior Insider
When flying from SXM to SBH is it better/smarter to reserve the earliest flight you can get and hope your plane from the US is not late, or reserve the latest connecting flight, and hope you can get on an earlier one?

For instance, if you were arriving in SXM at 2:15 and there are connecting flights to SBH 15 minutes to a half hour, should you be on the 2:45 flight or the 4:30 flight? Obviously the early flight gets you there a couple hours early, but the late flight has some padding and a safety factor built in.

Having an extra couple hours on the island is nice, but cutting it too close and having to spend the night on SXM is probably not worth the risk.

Anyone have any thoughts?
 
When connecting through SXM I book the later connection and then hope to get on an earlier flight.
 
We just booked Winair flights for February. Initially we requested the 2:30 PM but based on our arrival they suggested 3:00 PM and then made the switch once we gave the OK. This gives us 90+ minutes versus the 60+ we initially requested.
 
When flying from SXM to SBH is it better/smarter to reserve the earliest flight you can get and hope your plane from the US is not late, or reserve the latest connecting flight, and hope you can get on an earlier one?

For instance, if you were arriving in SXM at 2:15 and there are connecting flights to SBH 15 minutes to a half hour, should you be on the 2:45 flight or the 4:30 flight? Obviously the early flight gets you there a couple hours early, but the late flight has some padding and a safety factor built in.

Having an extra couple hours on the island is nice, but cutting it too close and having to spend the night on SXM is probably not worth the risk.

Anyone have any thoughts?
We use SBC and if the connection is tight they rebook us on a more appropriate flight. If we arrive early they do their best to put us on an earlier flight to SBH. No worries if we have to wait, gives us time to enjoy cold Caribe & pick up a bottle or 2 from duty free.
 
My experience with Winair is that they won't even let you book a flight with anything less than a 90 minute connection. They request your flight info coming into SXM and will adjust based on a 90 minute window. With the caveat that should you arrive at the gate earlier they will do their best to get you on an earlier flight.

I actually had to make an appeal last November because our flight from YYZ arrived at 4 pm'ish and I wanted to book the last Winair flight at 5 pm - carry on only blah blah. They said I could do so but I would have to incur the cost of overnight accommodations on SXM if we didn't make the connection. Fair enough.

Regardless, having a confirmed seat on a later flight versus missing an earlier flight due to a late arrival on a SXM would give me more peace of mind for sure. That way at least you're pretty much assured to be on SBH by dinner time!
 
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