Windstar Cruises Take a week (or two) to see the slower, sweeter side of the Caribbean on this line’s six-ship fleet, which takes a maximum of 310 cruisers to the region’s most secluded anchorages. You can’t go wrong with 212-passenger Star Breeze’s’ 14-day small ship cruises, which depart Barbados on November 18 and calls at Les Saintes in Guadeloupe, Anguilla, Montserrat and Dominica.