From Puerto Rico and the Virgin Islands (both US and British) to Guadeloupe, this collection of tropical islands offers a healthy variety of topography and culture. With reliable easterly trade winds and a tropical climate, these barrier islands between the Caribbean Sea and the western Atlantic form an idyllic water-oriented playground. There are excellent communication and travel options throughout the chain, though the islands further east provide a greater escape from civilization.
| 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 | 228' (69.49m) | 13 | 26 |
| 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 | 152' (46.33m) | 5 | 10 |
| Crew Type | Boat Type | Hull Type | Length | Cabins | Sleeps |
| Crewed | Power | Monohull | 120' (36.58m) | 4 | 9 |
| 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 | Sail | Monohull | 112' (34.14m) |