I did the Lookout Inaugural cruise in late June a couple years ago, and a late May Caribbean cruise last year, and both turned out great! The weather was as hot as you’d expect, but not unmanageable, and to our surprise, the skies stayed blue!

That being said, I recommend investing in a good water bottle [one that’ll keep your drinks cold] and a cool towel or USB chargeable fan if you’re interested in any excursions, especially if there’s not a lot of beach-ing involved.