My husband and I cruised again on Princess -- this time with 8 other family members (5 of whom had never been on a cruise).
We flew into San Juan the night before embarkation (booked our own air travel) for our Southern Caribbean Cruise over Christmas. Its ports of call were St. Thomas, St. Kitts, Grenada, Bonaire and Aruba.
Despite heading to the Port in San Juan at 12:30 to embark (my FIL did not want to tour the City even though we didn't have to be on board until 9pm), it was an absolute breeze. From the time we checked our luggage to the time we were in our Stateroom (Caribe 434), it took only about 45 minutes....and that's including embarking (slowly) with two 80-year old passengers. The San Juan Port is considerably cleaner and more organized than the Fort Lauderdale Port, from where we've embarked previously.