Our experience-
First trip - DD was exactly 3 months old on the day we left- truly a wonderful experience. At this point, she was exclusively breastfed. Major plus- at night, we were able to put her back in her stroller, fully reclined and she slept away like an angel with we did DTD or the Boardwalk. She also slept like an angel through all of our meals - including a wonderful steak dinner at Shulas. Major cons- because she was not eating ANY solids yet, we still had at least one very scary, potentially HUGE mess diaper per day (are all babies like this?? it got **much** better for her once we started some cereal!) The other "con" was that we we were still pretty "new" at the whole parenting thing (she was our first), so we came with QUITE the entorage of stuff (but we may very likely had done that the first time??)
Second trip - DD was exactly 7 months old the day we left - again, a truly wonderful experience. Big differences - she was eating some cereal and fruits/veggies (diapers weren't as bad, but a pain to express milk to mix w/ the cereal - that whole process seemed easier at home), able to sit up in restaurant high chairs (with the cover we brought from home). The pluses - things actually made her smile, since she had already started "swim lessons" at home, we were more comfortable taking her in the pool. It was fun to have her at the table with us, eating her saltines & cheerrios while we had our meal. The cons - she was less content at the meals (no longer sitting in the baby carrier, since she prefered sitting in the high chair.) We didn't "enjoy" our meals in the same relaxed way as when she was 3 months. ALso, it turns out lugging around baby food and trying to have the right "mix" was a bit of a pain.
As far as parks/riding went - we rode pretty much both times, discreetly nursed as needed, and all in all had a fabulous time.
If I had to pick, which would I do again? Both of course!

I'm already trying to convince DH that we need a December trip (our baby #2 will be 3 months) along with our annual May trip (baby #2 will be 8 months!)
One more piece of advice - for the littlest ones, I highly recommend a RayShade for your stroller and a stroller fan. The ray shads were great in blocking the bright sun and as long as they are too little to be grabbing at the stroller, I really liked the ventilation that the stroller fan gave when her stroller was fully reclined.