Hi Ana -
Welcome to the Moms Panel and thank you again for visiting! A Land and Sea combination vacation is a great way of vacationing with your family. The memories that you'll create will last a lifetime and you'll be glad that you are planning this event early, so you can really take advantage of having the best choices for your family.
The choice that my family has made in the past, has always been a trip to Walt Disney World first, followed by a voyage on the Disney Cruise.The first half of your vacation can be spent burning all that energy enjoying the rides and attractions at the parks. After a few days park hopping at Disney World, you and your family can enjoy some rest and relaxation on the Disney Cruise. If you stay on property, that would make it even more magical, since the magic will feel like it never ends. The transition from your Disney Resort to the Disney Cruise can be seamless, since Disney makes it so convenient for you and your family. Disney Cruise Line ground transportation is available to take you from the resorts to the port on your embarkation day. Then you are off to an awesome next half of your vacation, cruising to the Bahamas and spending the day at beautiful
Castaway Cay!
You can look forward to nice weather in May or June. The crowds may be busy, but it is pretty bearable. The last weekend in May is Memorial Day weekend, so you can expect a bigger crowd at the parks since it is a holiday weekend. I think you should be fine if your schedule fits after that holiday weekend and the beginning of June.
I hope this helps. Let us know how else we can help with your planning, Ana.
~ Dolly