I am a big fan of the repositioning cruise, having done several on the Sea Goddess (now Sea Dream). We always sailed the South Atlantic, starting in Madeira or Canary Islands to the Caribbean. The sea in October was always very very calm; almost lake-like. The ship always made a stop on an island prior to our final destination. A few times it was St. Barts, another Antigua or Anguilla. My understanding from the crew members is that the calmer waters are to be found going from Europe to Caribbean in late fall as opposed to the other direction in late spring. Great time to relax,unwind and catch up on your reading. We loved those cruises.