We took the Royal Clipper cruise around Italy 5 years ago for out 30th anniversary. Started in Rome, sailed to Sicily, Greece, Croatia, and ended up in Venice. The trip of a lifetime!
The sailing experience was unique. How often do you get to sail in a 5-masted square rigger? And the accommodations were luxurious. The music played while raising the sails at sunset was awesome. Boats came out from every port we visited to see the majestic ship. We felt like movie stars waving at the paparazzi.
The ship carries about 200 passengers and 100 crew. Most of the clientele is older; many are involved in sailing in some way. Many were repeat customers; quite a few had crossed the Atlantic in her on previous cruises.
I don't know if the Caribbean cruises are quite as "genteel."
On the square rigger we used the sails about half the time. The captain even sailed us out from the dock in one port when the wind was just right.
Because the two smaller ships are mostly fore-and-aft rigged the sails are used more frequently; they can sail closer to the wind and so closer to the desired course. (There are schedules to keep.)
I would do it again in a heartbeat if I had the money. But right now I am unemployed and raising 3 young grandchildren.
BTW, we found the best deal on tickets through BOAT US.
Royal Clipper Trip to Italy, Greece, Croatia pictures from cruises photos on webshots