We were on Windward in April 1997 -- in fact, it was exactly 10 years ago to the week. It was a seven-night cruise, roundtrip San Juan, with the following ports of call: Barbados, St. Lucia, St. Barts, Tortola, and St. Thomas.
The ship had not yet been stretched. We had also been on sister ship Dreamward a couple of years prior. Other than SS Norway, these two ships remain my favorites in terms of attractiveness (pre-stretch) with the tiered aft decks connected by staircase, the tiered area by the pool, and the huge oval window in one of the stair towers that made for great photo opportunities.
Our son was just three years old at the time, and I think this is the first cruise he remembers. He enjoyed playing basketball, and also tried several dishes off of the main menu for the first time.
Our favorite memory from that ship was one evening at dinner, when our son fell asleep right before dessert came. It was also the night the waiters did a big show, including the loud reggae music and a baked Alaska parade. Our son continued to sleep through the whole thing. We even have a few photos, including one taken by the ship's photographer.
A second favorite memory was viewing the Pitons in St. Lucia from the decks as we pulled in at about 5:00 am. A buffet breakfast was set up on deck, and classical music was played through the loudspeakers.
I had wanted to return to either Dreamward or Windward post-stretch (N. Dream or N. Wind, respectively), yet in the end I decided to keep my memories of the ship as they were.