With so much variety and easy sailing between islands, it's no wonder the Windward Islands (from Martinique south to Grenada) are such a popular cruising and charter region. The same easterly trade winds that named these the Windward Islands make for excellent sailing and pleasant tropical temperatures. Each island has its own distinctive flavor, stemming in part from its particular cultural heritage (French, English, Creole). While most of these are volcanic in origin and an easy day’s sail apart, Barbados is coral-based and a hundred miles upwind of the rest of the chain.
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 288' 9" (88m) | 6 | 12 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 248' (75.59m) | 6 | 12 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 223' (67.97m) | 6 | 12 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 200' (60.96m) | 6 | 12 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 192' (58.52m) | 6 | 12 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 164' 0" (50m) | 6 | 12 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 152' (46.33m) | 5 | 10 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Sail | Monohull | 112' (34.14m) | 4 | 8 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 111' 3" (33.91m) | 5 | 10 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Sail | Monohull | 72' 0" (21.95m) | 4 | 8 |