Island hopping across the Caribbean – Let’s explore here!

If you’re interested in island hopping across the Caribbean, we’ve planned an extensive journey across almost all of them. The mammoth trip starts in Aruba, and travels through 30 countries and territories ending in Bermuda. The route takes into account the lack of transportation options between the islands (correct as at January 2025).

Travelling overland between the islands is quite prohibitive due to the lack of transportation options. Travelling between different island countries via ferry is possible, however, ferries only operate between some islands. Chartering private boats between islands is also possible, although travelling with a car in this way is prohibitive. Flying is another option, although again, flights only operate between some islands.

Which Caribbean island countries and territories does the route take?

The journey travels from Aruba – Curaçao – Bonaire – Trinidad and Tobago – Barbados – Grenada – Saint Vincent and the Grenadines – Saint Lucia – Martinique – Dominica – Guadeloupe – Saint Barthélemy – Saint-Martin – Sint Maarten – Anguilla – Saba – Sint Eustatius – Saint Kitts and Nevis – Antigua and Barbuda – Montserrat – British Virgin Islands – United States Virgin Islands – Puerto Rico – Dominican Republic – Haiti – Turks and Caicos Islands – Bahamas – Cayman Islands – Jamaica – Cuba – Bermuda.

Each country and territory has an individual plan for exploring the islands, with road trip maps and driving conditions for almost every island. There’s also information on visas, as well as how amenable to being a digital nomad the country is, whether you will need a carnet, what time zone it’s in etc.

We’ve also included weather and climate information, so that you can avoid the bad weather and potential hurricanes, and identify when is the best time to visit the different islands in the Caribbean.

We’re also creating blogs for each country when we have data, or we can find decent wifi, and we have enough power!

If you’d like any information on any of these places, please don’t hesitate to contact us!