We have done two repositionings on the Jewel out of Boston and another that was roundtrip from Boston to Bermuda and the Caribbean. On one cruise there were high seas enroute to Bermuda because a hurricane was heading up the coast, but the ship rode them very well. The storm forced us to remain in Bermuda for several extra hours, but once we resumed sailing the seas were extremely calm. There is no predicting what the conditions will be even in the normally calm Caribbean.
Boarding the ship in Boston is an extremely smooth and easy operation and we especially love it because it is just a short drive from home.
We will be on the October 28, 2008 repositioning cruise and hope you will see fit to join us. There is a large contingent of folks who are anxious to reboard their favorite RCI ship. Check out some of the other cruise boards. Cruise Critic (I'm not sure I am allowed to mention other boards) has a thread where over 80 people have so far indicated that they will be on this sailing. Many of them are "Royal Jewels", a group that first sailed on this ship and itinerary in 2004, leaving Boston the day after the Red Sox won the World Series. Can you say"PARTY"?
If you have some more specific questions about the ship, itinerary or Boston please let us know.