Caribbean - Wisdom (or lack thereof) of potential same-day connections using separate tickets

I am trying to get to GEO from PHL. I plan to do that via two separate tickets: an award booking on AA via MIA to either POS or BGI, then a paid flight on LI from BGI-GEO or on BW from POS-GEO. This will be in late October/early November and seats are already filling up on the island flights, so I'd like to book pretty soon.

If I travel through POS, I can do it on the same day with a 7-hour layover on the outbound and a 1:20 layover on the return. (I can also book a 4:25 layover for the return but that gets me back to PHL in the wee hours of the next morning, which I don't want to do.)

If I travel through BGI, I can do it on the same day with a 6-hour layover on the outbound and a 1-hour layover on the return. (Here again, I can book an 11-hour layover for the return, but getting back to PHL at 01:20 is not desirable.)

I have zero experience with either BW or LI, and zero experience with POS or BGI. Do these airlines tend to have a lot of schedule changes and/or delays? Are the airports quick on transit time? If I do split my trips onto two separate days, which is the better place to do an overnight? (The overnight stay will likely be just time spent in a hotel, hopefully using HH/PC/SPG/Hyatt points and very close to the airport.)

A layover of only an hour or an hour and a half would make me very nervous coming out of GEO, especially on LI or BW, and even with printed boarding passes in hand and no luggage. My experience is that AA flights out of both BGI and POS tend to be very full. I would probably do the overnight if you don't want to arrive back late in PHL, and would choose BGI over POS.

Why not just take DL or BW from/through JFK straight to GEO? There have been some cheap fares reported recently -- you very well may find that it's not worth burning the miles, especially when you factor in the added ticket from BGI or POS, two sets of international taxes and a possible hotel.

That said, there are certainly worse things than a day in BGI.

Thanks, that is very helpful. I will look into the overnight in BGI--presumably there are some chain hotels there that I can use points for. After 10 days in Guyana, a night (or two!) in Barbados might be a nice thing.

As for "why not JFK," two reasons: first, the outbound is an obnoxious red-eye, and second, it's just a real pain for me to get there. I would have to either drive 3 hours (vs. 40 minutes from my house to PHL) or add a flight connection, which is also less than optimal since the flights between PHL-JFK are not that frequent. Flying from JFK generally means spending a night in a Queens airport hotel, which is just not something I feel like doing. Spending a night in BGI is a lot more appealing.

I'm doing something similar soon. Into POS on AA arriving around 10pm, and out on BW at 1am to GEO. Not too worried here - AA tends to be pretty on time.

However, on the way out, I wouldn't risk it. Both BW/LI can be a little...unpredictable supposedly (though I've not encountered major delays myself) - so I think I'd definitely take the overnight in Barbados option on your way back.

Thanks, that is very helpful. I will look into the overnight in BGI--presumably there are some chain hotels there that I can use points for.

There is a very nice Hilton. Also, a Marriott Courtyard.

Be very careful with Liat - - very unreliable and customer service is non-existent.