Hi Lottorus, and welcome to cruise-chat. And, congratulations on your 25th anniversary!
We cruise every summer as my husband is a teacher and we have a school-aged son. As school is not in session, prices tend to be much higher than at other times of the year. But, that's the only negative I've found for the time frame you wish.
True -- not too many ships in the Caribbean then. That's because many are repositioned to other areas, such as Alaska, Bermuda, and Europe. We did a cruise to Atlantic Canada last July and a couple of summers prior to that.
Tell us more about what you are looking for. Which is more important to you, ship or itinerary? Do you want a lot of different ports or more days at sea? How long a cruise can you take? And -- as summer is prime time for families to cruise -- would you prefer a ship or itinerary that might have fewer kids?