4 nights on the Dream departing from Port Canaveral going to CC and Nassau (which I'm not to excited about)
4 nights on the Magic departing from Miami going to Key west, CC and Nassau. Not sure about this one either since there are no at Sea days.
5 nights on the Wonder departing from San Juan arriving in New Orleans. only stop is CC. two days at sea but since
@lostpro9het mentioned the adult entertainment is meh has me second guessing.
I'm going to sound like a broken record, , since this is how I started my previous reply, but this depends heavily on personal taste.
I just did 4 nights on the Dream in April and had an AMAZING time. We had perfect weather and since we're not huge fans of Nassau, we stayed on the ship and had a lot of space to ourselves.
I love the Magic, and I haven't been to Key West in over 10 years. So this one would be my personal choice. The newer ships don't go to Key West because they're too big. So if you like Key West, the Magic is your best bet. Sea days are nice, but they're also when the ship is most crowded (obviously). So I would treat my day in Nassau as a sea day and enjoy the heck out of Key West and Castaway Cay.
If your son is really excited about San Juan, however, the Wonder sailing would be great. You could get into San Juan a couple days early and enjoy the city, then cruise to New Orleans. (Or you could stay in New Orleans a couple days afterwards.) On a 5-night sailing, I'm not sure what your adult entertainment options would be. Probably a comedian, a magician, or a juggler in the lounges in the evening. There might also be an "adult" game show, like "Meet Your Mate" (basically the Newlywed Game) or something similar. If those don't appeal to you, there's always a movie in the Buena Vista Theater. Your live shows in the Walt Disney Theater will be Disney Dreams and the Golden Mickeys (which is personally, my favorite DCL show). They're both classics! And you get a day at Castaway Cay.
I'm leaning towards the first one since it is our first cruise. I just saw there is another Miami one that is a 5 day cruise and added a day at sea but also jumped up around $1000.00. maybe a day at sea is worth it.
Longer is always better, IMHO, but you have to decide if the extra money is worth it. Is that $1000 per person, or total? That would make a difference for me.
Can you rent cabanas at the family beach like at the adult only beach?
Yup, and it's probably even more valuable on the family beach. It would be a great way to get away from any crowds, and still have access to the beach. Our cabana on Serenity Bay was very nice (my wife and daughter absolutely LOVED it), but I wouldn't say that we needed it. Serenity Bay is more laid back, and obviously quieter than the family beach. So I'm not sure I would do it again at Serenity Bay. But for the family beach, you might feel that it's well worth the money. HOWEVER, since it's your first Disney cruise, there may not be any cabanas available by the time your reservation window opens 75 days before sailing. Keep checking, though, because people do cancel as the cruise gets closer.
What is a placeholder for $250.00? Is that the same as booking it now?
A placeholder is a reservation that you make onboard for your NEXT cruise. It gives you a reservation number and guarantees your 10% discount and onboard credit, but you don't have to pick a specific date. Then when you know the exact sailing you want, you call and make your full deposit.
Dining rotation, is the later rotation better?
Again, this is simply personal taste. My family eats dinner at about 5 or 5:30, so we prefer early dining. However, families with young kids also like the early dining, so that in itself might be a reason for you to consider late dining. For me, if I sit down to a meal at 8 or 8:30 and I don't finish eating by 9:45, I will be uncomfortable when I want to go to bed. I prefer going to dinner and then enjoying the show afterwards. But my sister likes to nibble throughout the afternoon (chicken fingers, pizza, etc.) and she likes late dinner because if she has chicken and fries at 4:30, she's not ready for a big meal at 5:45.
Totally a personal choice.
Is food included in the cost?
Your meals at the rotational restaurants (including Animator's Palate) are included in your cruise fare. All the quick service food is included. (That includes soft serve ice cream, but NOT gelato on the Dream and Fantasy.) And meals at Cabanas are included (both the buffets at breakfast/lunch and table service for dinner). There is a limited room service menu that's also included. (I'm telling you, it's hard to beat having coffee and chocolate croissants delivered to the room in the morning and then eating them on the veranda!)
I know you pay for alcohol.
Correct, but they offer wine packages, and beer mugs that are refillable at a discounted price. Also, you can bring a couple bottles of wine onboard with you with no charge and can bring a glass to dinner.
And i'm gathering that Remy, Palo and Animator's Palate is extra
Remy and Palo are extra. (Although when you reach the Platinum Castaway Club level, you get one free meal at Palo.) As I mentioned above, Animator's Palate is included in your cruise fare. No upcharge for that.
Is Dining rotation extra?
Just in case you're still confused about this, the "dining rotation" is simply the 3 restaurants that are included in your cruise fare. You go to a different one each night, and your serving team goes with you. So you "rotate" through the free restaurants. There's no extra charge for the "rotation".
Is it best to look for excursions through Disney or on my own?
Another matter of personal taste. Booking through DCL is easier and more convenient. Easier, because it's done on their website or onboard. More convenient, because they tell you where to meet for the excursion and then walk you right to the bus or boat or tour guide. (This is definitely NOT how it's done on Norwegian Cruise Line. Ugh!)
However, you can book tours on your own that will having smaller group sizes, or even private tours. You can get them a little cheaper on their own, because DCL adds a little to the cost of the excursion to make a profit for themselves. If you want some suggestions for tour companies to look at, I'm sure people here will have some info to share.
One extra benefit of booking your excursion through DCL is that if your excursion is late returning for any reason, the cruise promises to wait for you. If you tour on your own, or with a private company and they can't get you back to the ship before departure time, you could be left behind. (Some tour companies promise to get you to the next port of call if they cause you to miss the ship's departure, so you want to check on that.)
Hope that's helpful.
so Port Canaveral is still high on my list.