Three friends and I recently did the 7-day Classic Southern Caribbean aboard the Caribbean Princess.
Ship Info: The ship itself was always kept sparkling clean. Despite others comments on the ship showing its age, if you're not microscopically analyzing things, there were no issues. Any time we were on the promenade deck, there were always workers painting and/or varnishing the wood railings, benches, deck etc. The ship is fairly easy to navigate. There was a good mix of ages on board as well. Very few young children, a hand full of teens, and a good balance of young-mature adults. The ship offers something for all ages.
Embarkation: We landed in San Juan at 11:30 and weren't through customs etc. until approx. 1:30 (there was a bit of a line up and only 2 customs officers working). We had pre-paid transfers and met the attendants at the exit of the airport that took us directly to the pier. Once at the pier, check-in was a breeze. We were in our room no later than 2:30. We spent the remainder of the day exploring and getting used to the ship.