Island hopping the Caribbean

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 is the end of the high season, so the weather is still nice but you will most likely find an empty beach too.

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.

How many countries are there in the Caribbean?

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

  1. Antigua and Barbuda
  2. 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

How to plan your island hopping the Caribbean?

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 this website for booking the best deals on flights anywhere in the world.

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.

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.

To give you a better insight, here is a little recap on each island.


Our island hopping started in Barbados and we really liked it here. We spent almost a week here and found the island big enough to keep ourselves entertained. The beaches are beautiful with white sand and despite the package holidaymakers, you can still find your private spot like on the Miami beach.

Bridgetown, the capital didn’t seem to win us over at all. Yes, we admit it is expensive to eat or drink out, but we only went to Oistins for the fish market to treat ourselves and otherwise, we found enough local eats to get by. In some way, we also had an amazing stay due to our Airbnb host. Find more details about our accommodation in our blog post linked below.

Here’s a discount of $55 when you use this link to book your first Airbnb stay.

Check out our blog post – How to visit Barbados on a Budget

Trinidad and Tobago

Trinidad & Tobago is known for its festival, but we were too late for the party. Instead, we were keen to try some of its food, which is quite unique in the Caribbean due to the influence of Indian immigrants. We tried doubles, roti filled with Indian curries, plus bake and shark too. If you head to the north side, you’ll find the nicest beach at Maracas Bay. Or you can check out the many waterfalls inland – Maracas Waterfall was our favourite.


Oh Grenada, you had us at your views of the harbour. We arrived in the middle of the night and woke up to stunning views of St George, the capital of Grenada. We went exploring the town and did a food tour to learn and taste some of the food on the island.

Grand Anse beach is where you want to go. A beautiful white sand beach with crystal clear waters and lined with almond trees. This is an island we would definitely like to return to.

Saint Vincent and the Grenadines

We considered travelling to St Vincent on a boat from Grenada, but it would take a few islands to hop and few ferries/boats. But if you have time this is a great option as you would get to see a few other islands such as Carriacou and Union Island.

We arrived in St Vincent and took the public bus to the top of the green hills where we stayed in our Airbnb. Everyone told us we must go to Bequia island which is accessible by daily ferry. We were promised some of the best beaches in the Caribbean and the island really delivered. This island was gorgeous.

Saint Lucia

We were all beached out when we arrived in Saint Lucia, so we decided to stay close-by Gros Islet and Rodney Bay. Our Airbnb place was super cozy and gave us a chance to catch up on some blogging and planning the upcoming island hopping.

We knew St Lucia was a popular stop for yachties and walking around the harbour we could see why. Gros Islet is known for its Friday street party, we ended up walking the colourful streets mid-week as we were leaving on Friday morning on a ferry. Yes, St Lucia is linked with 3 islands: Martinique, Dominica and Guadeloupe. The other main things to see or do here is Pitons – the volcanic peaks in the south of the island.


Dominica turned out to be a paradise! Its mountainous landscape offers insane views, there are waterfalls, beaches, great food and hot springs! Nicknamed “The Nature Isle”, it really lives up to its name! If you love adventure, you will love Dominica. We hiked up to Trafalgar Falls as well as Middleham Falls. We were set to hike up to the boiling lake as well, but unfortunately, due to the heavy rain, we had to change our plans.

The capital, Roseau offers market and streets with lots of small eateries where you can try local cuisine and mix with locals. You’ll find many great eco-friendly places on the islands. This is definitely the best island for independent travellers in the Eastern Caribbean.

Antigua and Barbuda

We were warned – the beaches in Antigua (pronounced An-tee-ga ) are some of the finest. We rented a car here for a few days to see what the island has to offer. Our road tripping started with a flat tyre within ten minutes. They say there are 365 beaches in Antigua and we think there might be 3650 potholes on this island too. We stayed for a few days and enjoyed the beaches and turquoise water here.

Saint Kitts and Nevis

Another flight took us to our country number 159 St Kitts & Nevis. This dual-island nation is one of the smallest in the Caribbean and we were almost at the end of our Eastern Caribbean island hopping trip. This was a popular place for family vacations for North Americans and Brits as well.

We checked out the Atlantic and Caribbean side which are only a short walk away from each other but overall thought it was very quiet as it seems most people spent their day in their resorts.

The Bahamas

The next country on our list was the Bahamas. We chose a flight that took us via Turks and Caicos islands. We stayed for 24 hours and we’re so glad we stopped here. The Grace Bay beach might be up there with some of the best beaches we’ve ever seen! It was hard to leave as we love beach time!

Our flight from Providenciales (Turks & Caicos) to the Bahamas was quite the surprise. We didn’t expect to be chauffeured there in a small 16 seater ex-private jet of a retired rockstar from the 80s. Well, that’s what it felt like for us. The only thing missing was a bottle of whiskey and some canapes. It was cool.

The Bahamas is a coral-based archipelago that has over 700 islands! We stayed on the main island of Grand Bahama although everyone will tell you that you must visit the smaller so-called family islands to see the real Bahamas. To try and keep costs down, we stayed with a local woman in a beautiful Bahamian Airbnb house, as this country is super expensive.
The Bahamas are definitely a popular tourist destination … here it’s all about the sun, beach and vacation! Due to it’s close proximity to the USA (the island Bimini is only 50 miles from Miami) this nation caters mostly to the US visitor. We beach-hopped, explored on foot and we ate some good seafood here.


Jamaica was next. We hired a car and set ourselves a very busy itinerary here. We wanted to see as much as we could in the time we had. Our favourite place was Negril for the great beaches and it didn’t feel too touristy. We spent a night at Treasure Beach, which is more aimed at independent travellers, however, Negril had a much nicer beach and vibe. The jerk chicken and rum tasted great in Jamaica and reggae music can be heard everywhere. We swam in the Blue Hole, visited the Bob Marley museum, enjoyed cold ‘Red Stripe’ beers on some white sandy beaches and met some very friendly Jamaicans.

Dominican Republic

This country has been on our bucket list for quite some time so we were excited to arrive. We booked a charming little hotel located in the historical centre in the capital city of Santo Domingo and we instantly loved the vibes here. A few reasons why we love the Dominican Republic.

It’s much more affordable than other Caribbean islands, our hotel in Santo Domingo was $35 p/n incl breakfast and the location was amazing! Good food and great coffee are everywhere, Uber is available to get around and everything feels affordable. We took buses to explore this island, different cities, beaches and areas and we loved it! The northern part of the Dominican Republic – Las Terrenas was our favourite. We’ll be back.

The Dominican Republic and Haiti share the same island – so why are they so different?


Only two more countries left to see on this leg. Next, we took a bus over the border from the Dominican Republic to enter Haiti. This was country number 164 and our last country in the Caribbean.
When you think of Haiti, you probably think of natural disasters… For instance, earthquakes or hurricanes. Sadly it is a country that only makes it into the news when something bad happens.

So here is something you might not know about Haiti and it’s positive! Near the city of Cap Haitien in the Northern part of the country are two main sites worth seeing. The first one is the largest fortress in the Americas – Citadelle Laferrière. The second one is the Sans Souci Palace. We visited both of them and had a great time in Haiti. Read more about our time spent here below;


Cuba was not on the itinerary during our island hopping in the Caribbean this time. We’ve been lucky to have previously visited and spent almost a month in Cuba in 2013. Cuba is incredible and still remains our favourite destination in this region. From white sand beaches, colourful houses in Trinidad and the sound of music in gorgeous Havana, Cuba offers so much.

We have travelled to Baracoa on the very end of the island and visited places such as Camaguey, Santiago, Cienfuegos and of course Vinales. Learning basic Spanish before you will definitely help you get a better insight into Cuba and its culture.

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