WWYD - help with my 2019 plans

Is the March cruise a Marvel day at sea cruise? And, if so, would that be of special interest to your family?

No, it’s not but we are more a Star Wars family anyway.

Remember the itineraries for the 2 shorter cruises might be the same. What if scenarios are tough because you aren't comparing apples to apples here. For me i would also stay with the 11 day. Its more of a once in a lifetime vacation, and can still be for your anniversary. Then perhaps opt for a shorter WDW trip in august for your actual Anniv. (but as a florida resident why anyone would actually want to be in Orlando in Aug is beyond me!)

The 5 night is Cozumel and Castaway and the 4 night is Nassau and Castaway. Fortunately the itineries are different.

We live in VA; it’s still hot in August and we don’t get an afternoon cool off rain. If I had to chose between two hot places, FL in August wins over Home every time. We tend to do a lot of park stuff in the morning and after the sun goes down.
 
I wonder if you'd prefer to have the cruise at the end of that trip though. It seems more relaxing that way. Also, prices the to be lower as you get later in August.

We’ve done a few 4 night cruises that if we felt we’d only chose that option if it covered our actual anniversary. And since we are a family of 5 the monetary difference between dates for a category 4 wasn’t significant between the middle of the month and end.
 
I'd lean toward a longer cruise, but for me, the caribbean isn't so interesting as to justify the high price of that 11 night, so in your specific case, I'd go with two vacations! I would personally love a week at WDW followed by a cruise :)
 

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