Ahoy there, Gretchen!
Welcome aboard planDisney! First off, a huge thank you to both you and your son-in-law for your service! As a fellow military member, I know just how much those family vacations mean, and what better way to make magical memories together than with a Disney cruise? So let’s talk about setting
sail from San Diego and picking the practically perfect voyage for your crew!
One of the best things about cruising with a two-year-old is that you’re generally not tied to school schedules, which gives you more flexibility in choosing your dates. Now, in my humble opinion, I’d recommend at least a 4-night cruise—those 3-night sailings go by faster than the Mad Hatter at a tea party, and you’ll be wishing for just one more day! Plus, on the 4-night sailings, you’ll get a full
Pirate Night (subject to change), which includes the themed menu at dinner, deck party, and (if history repeats itself) fireworks at sea! Right now, there are eight
4-night sailings from San Diego to choose from in 2026, giving you plenty of options to find the one that fits best for your family.
But if you want to really soak in all the magic, I’d personally go for the 7-Night Mexican Riviera cruise. This itinerary gives you three incredible port days in Puerto Vallarta, Cabo San Lucas, and Ensenada, plus three relaxing days at sea to fully enjoy everything the ship has to offer—from
Broadway-style shows to delicious dining and the best soft-serve ice cream supply on the high seas. The only catch? There’s just one 7-night sailing scheduled for 2026, departing April 24th through May 1st, so timing may be a factor.
Two verandah staterooms sound like a fantastic choice! If available, I’d recommend
connecting verandah staterooms, which allow you to open the partition between your balconies for a shared outdoor space—perfect for morning coffee with an ocean view or winding down under the stars after a fun-filled day.
Now, let’s talk about that little extra military pixie dust! Disney Cruise Line offers
military discounts on select sailings, but they’re usually released only 2-6 months before the sail date, and they’re never guaranteed. While those discounts can be an incredible value, I’d recommend booking now to lock in your preferred itinerary and staterooms.
No matter which sailing you choose, you’re in for an adventure filled with magic, memories, and maybe a few extra Mickey bars along the way. And just like Peter Pan, you’ll never want to grow up and leave the ship!
Sea ya real soon with love in the air and magic everywhere,
Dustin