While scrolling through some of our old saved spots on Google Maps, we stumbled upon a reminder that we had once dreamed of doing a Caribbean island-hopping adventure back in the winter of 2019. Funny how plans evolve—rather than hopping between islands, we ended up spending three unforgettable months cycling our way around the island of Cuba.
The Caribbean—officially known as the West Indies—is made up of well over two dozen islands, which quickly makes trip planning a challenge. To keep things manageable, we decided to focus this time on the independent island nations. That choice shaped an itinerary that will take us to nine of the thirteen independent Caribbean countries. If everything goes according to plan, we’ll have only two left unexplored—Haiti and Jamaica—having already visited Cuba and the Dominican Republic.
Click on photos below to see full size
Here’s a simple breakdown of the West Indies sub-region, as we came to understand it along the way.
| Sub-region | Island Group | Wind Qualifier | Island | Order of visit |
|---|---|---|---|---|
| West Indies | Lesser Antilles | Leeward Islands | [UK & US] – Virgin Islands | – |
| [FR & NL] – Saint Martin | – | |||
| Saint Kitts and Nevis | 1 | |||
| Antigua and Barbuda | 2 | |||
| [UK] – Montserrat | – | |||
| [FR] – Guadeloupe | – | |||
| Windward Islands | Dominica | 3 | ||
| [FR] – Martinique | – | |||
| Saint Lucia | 5 | |||
| Saint Vincent and the Grenadines | 7 | |||
| Barbados | 4 | |||
| Grenada | 6 | |||
| Trinidad and Tobago | 8 | |||
| – | [NL] – Aruba | – | ||
| [NL] – Bonaire | – | |||
| [NL] – Curaçao | – | |||
| Greater Antilles | – | [UK] – Cayman Islands | – | |
| Cuba | Visited | |||
| Dominican Republic | Visited | |||
| Haiti | Not visited | |||
| Jamaica | Not visited | |||
| [US] – Puerto Rico | – | |||
| Lucayan Archipelago | – | Bahamas | 9 | |
| [UK] – Turks and Caicos Islands | – |