This is all opinion from someone who has cruised 19 times in Disney, all cabin levels, 3-nights to 25-nights (that was a 14- and 11-night sailed back-to- back). I have also cruised with other lines.
First cruise : I would suggest you find one that is longer than 3 days. Four as a minimum. Five nights with a double dip ( 2 stops at Disney’s private island in the Bahamas if you like a low-key beach holiday); these are harder to find on the schedule. Seven nights if you have the time.
Being old-school, I recommend you get on the Magic, the original ship built for
DCL. She and her sister, the Wonder, are smaller and a bit more intimate. The staterooms are a little bigger, too. Doing the 5-night Double Dip of a Bahamas itinerary.
My second recommendation is an Eastern Caribbean on the Fantasy. St Thomas, Tortola, and
Castaway Cay as ports. The water is beautiful; St Thomas is easy and has a bunch of beaches. If you like Cozumel, look at a 7-night Western Caribbean or a cruise out of Galveston or New Orleans (these two options are becoming more standard; they used to be rare itineraries).
If you have the time and money, look at the 8-10 night cruises to the Southern Caribbean, which are rarely offered.
With each new set of ships (Magic and Wonder, late 1990s), Dream and Fantasy (early 2010s), and now the Triton-class (Wish 2022, to be followed by her 2 sisters), the size of the ship and the water rides on the pool deck have gotten larger. That is the most glaring difference among them.
They all offer a fairly similar experience - a rotational dinner program, wherein all guests will dine in each of the three dining rooms over the course of the cruise. No one misses out on any menu and your servers are the same in each of the venues. Dinner is in the dining room; the buffet and one sit-down restaurant is open for lunch.
The two dinner times allow all guests the opportunity to see the evening show in the theater. There are 2-3 Broadway-style (and quality) Disney-themed shows on every cruise. Unless you are in Alaska (or other rare locations) you can expect an evening event with a Pirate’s Party and fireworks.
It really comes down to budget, where, when, and how long you want to be on vacation.
I also like sailing from Port Canaveral, as the cruise terminal is dedicated to Disney and begins the cruise from the time you get out of your car / shuttle,… and walk through a giant Mickey head onto the ship.
If you like more relaxation, try to avoid school breaks.
You don’t need the most expensive room when starting your cruise life; you can save that money now and go on more cruises.
You can have a great time on any
Disney cruise! And, no I didn’t forget to mention the Wish. I just haven’t experienced it yet. Waiting for the price to level out after it‘s inaugural year.
Edit: (Wow - just re-read your initial post. I think I strayed a bit from discussing your original question.)
