Island Windjammer Cruises

Island Windjammers Cruise Schedule and Rates

Ahoy there!

Two frequently asked questions are "When is the best time to sail?" and "When should I reserve my cabin?"  We like to say that any time is a good time to sail! The weather in the Caribbean is warm and balmy year-round. Winter months are busier, because folks are trying to escape the cold back home.

Tropical storm season is June 1 through November 30. During the peak storm months of August through October, we move our ships to the southern Caribbean, where storms are less likely to occur. We also lower our rates!

Our ships are popular and have small capacities. We suggest that you reserve your space as soon as you decide on a preferred ship and sail date.

If you have questions, please call us Monday through Friday from 9:00 to 5:00 EST, or email us at

We're standing by to assist, and look forward to seeing you on deck!

Click here to view our Rates & Schedule

The Island Girls

Island Windjammers