Ahoy Crystal!
Thanks so much for stopping by the Disney Parks Moms Panel as you begin the planning stages for your inaugural voyage aboard Disney Cruise Line! I remember planning my very first cruise and how I had similar questions sailing around my head. I've now been on many Disney Cruises at all different times of the year and can honestly say that you can sail on any one of the four vessels, at any time of the year, and have the best vacation ever!
Your pirate princess will have an abundance of activities to choose from on all four Disney Cruise ships. All four ships have Youth Clubs, the Bibbidi Bobbidi Boutique, deck parties galore, Royal Court Royal Tea and splashtacular pools! I truly believe that any of the four ships will be a perfect choice for your daughter's first cruise. I suggest thinking about choosing an itinerary that sounds exciting. For example, I highly recommend your family choosing an itinerary that visits
Disney's private island, Castaway Cay, for your first voyage with Captain Mickey! Once you narrow down the time of year and itinerary, it will help make the decision of which ship easier because not every Disney Cruise ship embarks on all the itineraries throughout the year.
Once you choose the itinerary, that will help decide which port of call you leave from. We've had the opportunity of experiencing multiple ports of calls and they've all been lovely! Our favorite to sail out of is Port Canaveral in Orlando. However, you spend such a short amount of time at the port that I suggest really focusing on choosing an itinerary. Our favorite time of year to sail is late spring/early summer or around the holidays. The ships are decorated so beautifully during the holiday season! We also like sailing in January because it's wonderful escaping the winter cold! No matter what time of year you choose, your first Disney Cruise will be magical!
Beth