When moving from one destination to another requiring a short travel time, I have found it is better to match the timing of the flights/ buses or trains to the check in timings of the hotel.

Across hotels, most check in timings are around 12 p.m. to 2 p.m. Taking flights that arrive too early before check in timings of a hotel is a gamble as you may not get a room right away.  Afternoon flights or travel, if possible, are not as expensive as morning flights and can be considered for short hauls (especially between Tuesdays and Friday afternoons as the fares are lower). This ensures you reach your next destination, around the time when the hotel check in is open and you don’t have to again hang around to wait for your room while it gets ready (hotels politely turn down requests for early check in quoting rooms are not available but they do try their best if you add that you are willing to pay for early check in). So, I generally avoid early arrival times for check ins.

Again, check outs across hotels are between 12 p.m. to 2 p. m. Taking late evening or night flights are not convenient, as you may have to pay for a late check out, or keep your baggage at reception while you hang around to leave for the airport. Going to the airport too early also ends up with the entire family just hanging around again (more dangerously with the multiple distractions in the airport, money wise). It is just best to check out and head straight to the airport, bus or train station, in time for your trip.

I have found, that afternoon flights fit seamlessly with hotel policies of check in and check out, without wasting time in between (I do not like to request, coax, argue and ask for more than what I booked, knowing the hotel policy). This way, I can plan better for the morning half before leaving the hotel and evening half after arriving at the hotel.