September in Indonesia, where’s favorable?

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There is one flight a day Kupang to Alor. Don’t believe web sites that give you a second flight later in the day. It never flies. The first flight is a Wings Air flight and luggage is an issue. Overhead space is small - too small for my carry on. Purchase in advance if at all possible. I had no issues with 45k luggage except for paying for it.

You can fly out of Alor to Bali easily just not the other way without an overnight stay in Kupang.
To Bali direct from Alor?
 
Gotcha. So an extra leg via Bali on the way back to Jakarta rather than spending the night in Kupang. Might as well add a couple relax days there before heading to Jakarta.

No need to spend the night in Kupang on the way out of Alor. The flight through Kupang to Bali is an easy route, and also the fastest flight to Jakarta. There is no direct flight to Jakarta from Kupang that leaves after the flight from Alor arrives. You have to stop at either Bali or SUB. I like to spend a couple of days in Bali so that is my preferred route.

It just does not work going the other way unless you take the 2:00 AM flight out of Jakarta which arrives in time to get the flight Kupang to Alor. The first flight Bali to Kupang does not arrive in Kupang until after the Kupang Alor flight leaves so you have to spend the night in Kupang. Typically the international flights I get arrive in Jakarta too late to reliably connect to the 2:00 flight so I typically take a later flight and then spend the day and overnight in Kupang rather than overnight in Jakarta. An interesting hotel is La Hacienda - near the airport, reasonable bed and room, excellent food and an "interesting" mexican decor. The rooftop bar and restaurant is a good place to recover from jetlag.
 
Thanks @Luko @Darnold9999 Really appreciate the guidance. Looked at few alternatives and arriving on a Quatar flight in Jakarta on Sunday morning, scheduled @07:30, will it be feasible to catch the Lion 09:00? No room for anything. There is a safer one leaving 14:40 that arrive in Kupang 19:50 (both of these have 45 minute SUB stop over) but will they transfer me to Alor that late? 10 days in Alor.
Then back on a Wednesday on a direct to Bali leaving 13:50, I guess they time transfer for that one? Stay a couple of nights in Bali and then fly to Jakarta and home.
 
Thanks @Luko @Darnold9999 Really appreciate the guidance. Looked at few alternatives and arriving on a Quatar flight in Jakarta on Sunday morning, scheduled @07:30, will it be feasible to catch the Lion 09:00? No room for anything. There is a safer one leaving 14:40 that arrive in Kupang 19:50 (both of these have 45 minute SUB stop over) but will they transfer me to Alor that late? 10 days in Alor.
Then back on a Wednesday on a direct to Bali leaving 13:50, I guess they time transfer for that one? Stay a couple of nights in Bali and then fly to Jakarta and home.

I would not attempt the 9:00. You would probably clear customs and get to a different terminal building in 90 minutes, but it would be very close. if anything goes wrong you would not make the flight. The 14:40 would be safer. You will need to overnight in Kupang and get the first flight in the AM. If you can try and get the Jakarta to Alor connection on a single ticket then you will get some luggage allowance. Otherwise there is no included luggage on the Kupang Alor leg. Don’t know if that is possible for the 14:40 flight.
 
I would not attempt the 9:00. You would probably clear customs and get to a different terminal building in 90 minutes, but it would be very close. if anything goes wrong you would not make the flight. The 14:40 would be safer. You will need to overnight in Kupang and get the first flight in the AM. If you can try and get the Jakarta to Alor connection on a single ticket then you will get some luggage allowance. Otherwise there is no included luggage on the Kupang Alor leg. Don’t know if that is possible for the 14:40 flight.
Yeah, it sounded tight. I suppose local Lion Air flights don’t show up on your regular booking sites? How do you get a Qatar flight from Europe to Jakarta on the same ticket with Lion Air Jakarta-Kupang? And the Kupang-Alor-one? Only works Sunday and Wednesday it says, that sounds like an extremely local one.
 
I meant the Jakarta to Alor trip in a single ticket. Try NusaTrip for local Indo flights. Also the app BookCabin for Lion Air/Wings flights.
 
Wings, which is part of the Lion Air group. I just looked and it seems the only way to get Jakarta to Alor on a single ticket is to fly the 2:00AM Batik flight (Batik is also part of the Lion Air group). I did it one year across multiple days, but that was Lion Air rescheduling me not me booking the flights myself.
 

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