Of the ships you list, DH and I have sailed on the Explorer, Liberty, and Freedom. We have also sailed numerous times on other ships of the same three classes. We really liked the Freedom, but it’s been more than 10 years since we were last on it, so no experience with its amped version.
TL:DR You have a hard choice! So many variables. So much depends on your group and what their priorities are.
Over the years, once we sailed on a Freedom class ship, we stayed with that size for Caribbean trips, until Oasis came out - and then we stayed with that class. After doing Oasis class several times, we decided we’d like to step back down to Freedom class for the next one. But then Covid, plus we now winter in AZ. Last fall we resumed cruising, and we did two sets of back-to-backs on Voyager class ships, (Explorer for the Southern Caribbean itinerary, and Navigator because it was based out of Los Angeles and we could easily drive to it).
We’ll now stick to ships bigger than Voyager class, when we can. We really noticed the lack of free dining options on that class, compared to the bigger ones - in terms of breakfast/lunch/snack/late-night snack. The Mexican grab’n’go El Loco Fresh was a nice addition (on the pool deck) on Navigator… Really compare the food offerings on each ship.
Your cruises are only 4-5 nights, so you might not feel that food pinch as much. If you choose to spend on specialty dining, you’ll have more options - even for lunch.
The bigger the ship, the more dining, drinking, activity, and entertainment choices - but you know your group and how much that matters.
For private islands, Coco Cay is better than Labadee, but you can still have a nice time at Labadee.
Jamaica vs Nassau vs Cozumel vs Puerto Plata - that should also be a big factor in choosing a cruise. So much “port enjoyment” depends on what your group likes to do, not just what the port has to offer.
And 4 vs 5 nights - we always like the longer cruises!
Sorry, no simple answers!
