After six months spent in West and Central Africa, we were ready for some sun, beach and some visa-free countries. Naturally, island hopping the Caribbean seemed like the perfect idea. Over 7,000 islands surrounded by turquoise waters and home to pristine white beaches just waiting to be discovered – yes, please. It was a perfect time as well. March and April are great months to go, it is the end of the high season, so the weather is still nice but you will most likely find an empty beach too.

Island Hopping in the Caribbean Beach

The Caribbean is a unique part of the world where most of the visitors come on pre-arranged packages, resort stays and of course as part of the ever-expanding cruising industry. Independent travellers keen on island hopping are quite rare. As expected the islands do cater mostly for cruisers and resort stayers.

But with a bit of planning and knowledge, island-hopping across all 13 independent countries is possible. And if you are lucky you might visit a few islands that despite being overseas territories, they’re also worth visiting. But most importantly there are islands that offer a lot more than just a beach.

In this article, we provide some information on our experience in the Caribbean in April 2019 and ALL updated information on airlines and ferries in 2022.

How many countries are there in the Caribbean?

There are 13 sovereign countries in the Caribbean and it is possible to visit them all in just one longer trip.

  1. Antigua and Barbuda
  2. The Bahamas
  3. Barbados
  4. Cuba
  5. Dominica
  6. Dominican Republic
  7. Grenada
  8. Haiti
  9. Jamaica
  10. Saint Kitts and Nevis
  11. Saint Lucia
  12. Saint Vincent and the Grenadines
  13. Trinidad and Tobago

Additionally, these are the overseas territories in the Caribean:

  • British overseas territory: Anguilla, British Virgin Islands (Tortola, Virgin Gorda, Anegada, Jost Van Dyke), Cayman Islands, Montserrat, Turks and Caicos Islands
  • France overseas territories: Guadeloupe, Martinique, Saint Barthélemy, Saint Martin
  • USA overseas territories: Puerto Rico, United States Virgin Islands (Saint Croix, Saint John, Saint Thomas)
  • Overseas territories of the Netherlands: Bonaire, Sint Eustatius, Saba, Aruba, Curaçao, Sint Maarten
Map of the Caribbean

Map of the Caribbean

By the way, did you know the Caribbean is part of the North American continent? Find out more about it here: How Many Countries in North America? Why 3 is The Wrong Answer!

How to plan your island-hopping Caribbean itinerary?

Getting to the Caribbean is not particularly hard, there are plenty of direct flights from Europe and North America to get you there. If you are travelling on a budget, the best option is to search for European charter flights to Barbados, Guadeloupe, or Martinique and start your travels from there.

We use Aviasales to book the best deals on flights anywhere in the world and great to create the most cost-effective Caribbean island-hopping itinerary.

Are you coming from Canada or the USA? Well, you are spoilt for choices of flights and can possibly do your Caribbean Island hopping in a few segments. If you are aiming to visit all of them, a good idea might be to start in the south (ie Trinidad or Barbados) and hop your way north.

Or start in the Bahamas and make your way south. 

I know how to find and book cheap flights and I can also help you choose the right luggage: Backpack Vs Suitcase – which one should you choose? 

Island hopping the Caribbean as an independent traveller – What is it really like?

I admit it, island hopping the Caribbean can be lonely at times. It’s harder to meet other travellers and hopping from island to island can be costly as there are simply no cheap flights (minimum of $100-$150).

There are not that many ferries (mostly in the Eastern Caribbean) and you could possibly help out on a boat to catch a ride to the next island but that does require more time and waiting around.

Caribbean Islands Hopping backpacking

Backpacking the Caribbean Islands

Island hopping the Caribbean – Ferry vs Flights vs Cruise

Cruises around the Caribbean

I am personally not a big fan of cruises. You have limited time on each island, the whole concept of cruise enriches the people who own them and little goes to the actual islands. It’s also very bad for the environment.

Locals in the Bahamas said to me that according to the statistics, cruise visitors only spent 10 USD on the island, as they eat and drink on the cruise ship and organise trips through the cruise as well.

But I know many people are simply short on time and cruises can offer amazing value. Or for those with a fear of flying, this can be the perfect option to visit the Caribbean. If you do choose to book a Caribbean Cruise, try to contribute to the local’s economy, rather than booking excursions from the cruise company.

How to fly around the Caribbean?

There are two options here. You can either fly in and out of the most of islands from Miami. Or you can connect them with small Caribbean Airlines, but this requires some planning as flights are not daily and a few were cancelled during the pandemic.

Here are a few airlines to look at and again the best way to search for prices is on Aviasales.

InterCaribbean Airways, Ltd. is a passenger airline based in the Turks and Caicos Islands flying to Antigua, The Bahamas, The British Virgin Islands, Cuba, Dominica, Dominican Republic, Haiti, Jamaica, Puerto Rico, St. Lucia, Barbados, Grenada, St. Vincent and the Grenadines, and St. Maarten. You can find the current schedule here.