Originally Posted by
bpk6h
I've had to do many Eastern seaboard connections to SQ at JFK/EWR (but not from locations that SQ sells a connecting flight so I buy my own). It's never ideal but I always give myself a wide berth for the connection...for JFK I usually fly mid morning to arrive around noon-1pm. Last time I got a day room at the TWA Hotel. If you can change the JBU flight for $75 and have the day to spare, I would do that and just pick up your bags at JFK and recheck them for the SQ flight.
Speaking as someone who flies between BOS and SIN fairly often I think separate tickets makes more sense even if SQ is willing to sell you a B6 connection — if you're fine with spending a day in JFK then booking BOS-JFK and JFK-SIN separately is usually cheaper, and it's much easier to change the BOS-JFK leg (or just switch to Amtrak) as well. Plus if you book on DL and have no checked bags you don't even need to reclear security and can get a BP printed at the gate (and if you have an SC membership you can just wait out the connection in the club as well).