I did Valparaiso to Fort Lauderdale on Celebrity in April. Weather was chilly in Chile

p) but warmer further north. The cruise was 15 days and that was plenty long enough for me, and I pretty much never want to go back to South America (dirty, poor, full of touts and pickpockets who prevent you from enjoying the sights). There was norovirus on board - that was no fun at all. There was one rough day in the Caribbean between Cartagena and Jamaica where they closed the pool deck due to the rough seas - the crew said it is often rough in that patch of sea. (There wasn't much water left in the pool anyway, most of it had sloshed out due to the rolling). Disembarkation at Fort L was a nightmare. The US citizen line moved reasonably quickly but the line for other passports was glacially slow (2.5 hours standing in line) and many people missed their post-cruise shore excursion departures because of it. If you are allowed to get off the ship carrying your own bags immediately after docking then my advice would be to do that as then the immigration line is likely to be more manageable.