We arrive by cruise ship at the Southampton Port on Wed. May 15. Usually, passengers can disembark around 7-7:30. Do you think the 10:55 flight is cutting it too close? The next flight isn't until late afternoon.
If the ship is on time AND you self-disembark (take your own luggage off), yes.
If you are dis-embarking in cohorts with the ship handling your luggage, then no way.
BUT there are many reasons why the ship might be late- severe weather, an earlier mechanical issue, a medical emergency at sea requiring air evacuation, attending an SOS at sea etc etc.
I have had enough late arrivals, and even port changes that there is no way I would risk the morning flight.
The late afternoon flight would be more sensible.
I would also err on the side of caution and book the afternoon flight!
Definitely take the late afternoon flight. Having taken many cruises, I've seen enough things delay disembarkation that I'd never cut it that close. Being bored at the airport with lots of time to spare isn't a big deal. Missing the flight is a big deal. Not the way to end a cruise.
And if you have several hours in hand Winchester is only 15 minutes by train from Southampton Airport Parkway Station.
There is left luggage at the airport for £10 per bag per day.