Island Hopping the Caribbean – 13 AMAZING Islands

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.

Island Hopping the Caribbean – 13 AMAZING Islands

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.

Hi, we’re Rach & Marty!

We’ve visited every country in the world and want to help you get the most out of your travels!

Whether you need an expertly planned itinerary, some experienced hints and tips, or just craving a delicious food adventure, we’ve got you covered!

Hi, we’re Rach & Marty!

We’ve visited every country in the world and want to help you get the most out of your travels!

Whether you need an expertly planned itinerary, some experienced hints and tips, or just craving a delicious food adventure, we’ve got you covered!

Hi, we’re Rach & Marty!

We’ve visited every country in the world and want to help you get the most out of your travels!

Whether you need an expertly planned itinerary, some experienced hints and tips, or just craving a delicious food adventure, we’ve got you covered!

We may earn affiliate commissions from websites we link to, at no cost to you. Click here for details.

Island Hopping in the Caribbean Beach

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.

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, some islands offer much 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 2024..

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 Skyscanner 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 fantastic value.

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 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 most of the 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 Skyscanner.

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.

Island Hopping Caribbean - Route Map InterCaribbean Airways Credit_ InterCaribbean Airways
Island Hopping Caribbean – Route Map InterCaribbean Airways Credit_ InterCaribbean Airways

LIAT (Leeward Islands Air Transport) has its headquarters in Antigua, and it is the best airline to use for island-hopping the Caribbean as it connects many islands.

We used LIAT the most. Click here for the current flight schedule with LIAT.

Caribbean Airlines – The Trinidad Tobago-based carrier flies to 14 island destinations St. Maarten, Antigua, St. Lucia, St. Vincent, and Nassau, Bahamas to name a few.

Island Hopping Caribbean - Route_Map Caribbean Airlines
Island Hopping Caribbean – Route Map of Caribbean Airlines Credit Caribbean Airlines 

Air Caraibes based on the French island Guadeloupe, mainly services the French Caribbean islands: St. Barts, Martinique, and 14 other island airports across the region.

Cayman Airways flies from all three Cayman Islands to Cuba (Havana) and Jamaica (Kingston and Montego Bay). Click here for the current flight schedule for Cayman Airways.

Bahamas Air is based in Nassau Bahamas and connects several cities in Florida, but also connects Turks and Caicos, Havana, Kingston, and Santo Domingo, Dominican Republic.

Caribbean Ferry between 4 Islands

If you plan to island-hop the Caribbean with ferries, I have bad news. These are not really the Greek islands, and a majority of the Caribbean islands don’t have standard passenger ferries.

I mean, there are small ferries, like in St Vincent and the Grenadines where you can take a ferry to the next islands, but when it comes to international crossing, there aren’t many.

There is one ferry that connects 4 different islands: L’Express des Iles (translates to the express of the Islands).

L’Express des Iles offers a dependable, inexpensive, and pleasant ferry service between the islands of Martinique, Guadeloupe, Dominica, and St.Lucia (and Marie Galante and Les Saintes). You can book your ticket online easily and see the cost and schedule. The website is in French only, however. 

Island Hopping the Caribbean - Ferry Service

Our Island Hopping the Caribbean in 2019:

To give you a better insight, here is a little recap of each island. Yes, things have changed since the pandemic, but the cost or vibe of these islands will be the same. Our island-hopping Caribbean itinerary started in Barbados and finished in Haiti.

Barbados

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 entertain ourselves.

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 a fantastic stay due to our Airbnb host.

Find more details about our accommodation in 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.

Grenada

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.

Here are our top 10 things you shouldn’t miss in Grenada.

Grenada Caribbean Islands Hopping - Beach
Caribbean Island Hopping – Beautiful beaches of Grenada

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 a few ferries/boats. But if you have time, this is an excellent 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, and there are a bunch of amazing things to do here.

Saint Lucia

We were all beached out when we arrived in Saint Lucia, so we decided to stay close to Gros Islet and Rodney Bay. Our Airbnb place was super cosy 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 it’s beautiful here. 

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.

Caribbean island hopping by boat would be the best way to see the islands. There is only one ferry that links 4 islands. 

Yes, St Lucia is linked with 3 islands: Martinique, Dominica, and Guadeloupe.

The other thing to see or do here is Pitons – the volcanic peaks south of the island. Check out the great range of Pitons hikes and day tours available.

Don’t miss our recommendations for the Top 5 Amazing Hotels in Saint Lucia. Some of these properties must be seen to be believed.

Dominica

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 also set to hike up to the boiling lake, but unfortunately, due to the heavy rain, we had to change our plans.

The capital, Roseau offers markets and streets with many 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 with a range of great things to do.

Antigua and Barbuda

We were warned that 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 offers. Our road trip 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.

If you’re in Antigua for just the day as part of a cruise, then this Shore Excursion to explore the whole island. The tour includes pick-up and drop-off from the port, and you’re guaranteed to be back in good time before your ship sets sail again. 

Antigua Barbuda Caribbean Islands Hopping
Caribbean Island Hopping involves a lot of beautiful beaches

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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.

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

Are you island-hopping the Caribbean on a cruise ship or only got the day to explore Saint Kitts? I recommend this great valued Shore Excursion of Saint Kitts island.

The tour includes visiting famous landmarks such as Independence Square and Romney Manor, and you will have free time to swim or shop before being transferred back to the ship before departure.

The Bahamas

The next country on our list was the Bahamas. We chose a flight that took us via the Turks and Caicos Islands. We stayed for 24 hours, and we’re so glad we stopped here. 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 a 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 a popular tourist destination … here it’s all about the sun, beach, and vacation! The incredibly popular excursion to Rose Island to swim with pigs might be for you.

Due to its proximity to the USA (the island Bimini is only 50 miles from Miami), this nation caters mainly to US visitors. You can take this day trip to Bimini from Miami or the Bimini Express Ferry and Beach Day Pass from Miami too.

We beach-hopped, explored on foot, and explored the area in search of the 10 best foods in the Bahamas. We gave it a solid effort; the seafood, in particular is fantastic and fresh.

Caribbean Island Hopping - Bahamas
Caribbean Island Hopping – Bahamas capital Nassau

Jamaica

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 fabulous 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 white sandy beaches and met some very friendly Jamaicans.

Did you know there are 2 Jamaica languages?

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, including breakfast, and the location was terrific! Good food and great coffee are everywhere, Uber is available, 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 to eat more of the fantastic food in the Dominican Republic, too.

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

Haiti

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. We enjoyed exploring the colourful city and things to do in Cap Haitien. Our highlight was visiting the Citadelle Laferrière, what an adventure!

We really enjoyed the many flavours of Haitian cuisine, and we almost made it through these 10 best foods you should try in Haiti. This country is fascinating, and we learned quite a few surprising things we didn’t know about Haiti.

Haiti Caribbean Islands Hopping
Welcome to Haiti!

You might also enjoy reading our post about the 11 Caribbean islands’ best beaches.

We travelled through many countries in 2019, around forty of them to be exact. That year, we visited many Caribbean Island nations, and you can read our recap of the Caribbean islands and countries visited in 2019.

Travel Tips for North America

We have many travel guides and tips for North America— a fascinating continent!

We love travelling in Mexico and have many food and detailed guides. Read them here

These top 6 travel hacks to save money are great to read when planning your travels.

Are you interested in visiting these 15 best places to travel in the USA,  the ten best foods in New York, or searching the 12 best cheap eats in Vancouver?

If you plan to travel long-term after leaving North America, these 21 cheapest countries to visit will help you make your hard-earned dollars stretch a bit further.

For food lovers, don’t miss our top 10 countries for foodies; one is in North America.

You’ll need to stay connected while travelling in North America. We recommend eSIM. They’re easy, reliable and affordable. View eSIMs for individual countries, or consider a regional eSIM for North America.

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If you want to travel with like-minded travellers, consider joining a group tour. View the best deals on group tours in North America.

Check out our best-ever travel tips compiled from more than twenty years of experience.

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Tasty Food Adventures

20 Comments. Leave new

  • Hi Marty,

    I had no idea there was so many countries and territories in the Caribbean. Absolutely amazing facts. Always love images of Cuba with old cars. I must get there to have a look one day. Thanks for the great information. I must print it all out.

    Cheers Sharon…

    Reply
  • What fun to read. I am going this winter and getting ideas. I too adore Cuba though Trinidad was a bit touristy.

    By the way this might interest you. http://pvewood.blogspot.com/2013/04/25-reasons-why-i-love-living-in-romania.html

    Reply
  • Hey, I am actually going to do this starting from dom republic, I am hoping to go to Haiti after and then to Jamaica followed by Barbados and all of the island backwards. How do you recommend I should do this?
    I couldn’t find any flights from Haiti to Jamaica

    Reply
    • Hi Alan, thanks for your comment. There are no direct flights between Haiti and Jamaica so you would have to either transit via Turks and Caicos or The Bahamas, but not sure if those flights connect well. Maybe you could visit the Bahamas first and then fly to Jamaica? Of course, there are usually flights via the USA (Miami often) it just means you’d have to transit there. Check out this website to find the flight connection, then you can book them online. https://www.flightconnections.com. Have fun.

      Reply
  • Thts a fantastic idea I will go to Bahamas and then go to Jamaica after which I can do the tour as you did but backwards perfect, do you think I should be ok to cross the Dominican Republic Haiti border or I should just book the flights I am in Venezuela now and absolutely loving it

    Reply
  • Hi!

    Did you take flights for all of ’em? or ferries too?

    Reply
    • We took A ferry between St Lucia and Dominica. That’s the only international ferry I believe. I have just updated the blog post with additional practical information on flights as well as on the ferry. Enjoy and happy travels.

      Reply
  • Hi! I am also interested in traveling all the Caribbean countries. How long did it take for you to visit all of them and how many days did you need on each island?

    Reply
    • Hi Rachel, we spent 8 weeks across these islands mentioned in the blog. On some smaller islands we spent 3-4 days, we had a week in Barbados and we spent more time in the Dominican Republic and Haiti as there was more to see. We visited Cuba a few years back, where we spent 3 weeks.

      It also depends on the flight schedule as some islands are only connected with limited flights. Hope that helps.

      Reply
  • This was so helpful!!! Can you let me know your 2 favorite islands? Because I know asking for 1 is not fair haha

    Reply
  • Hi Marty, I’m planning on going and exploring the Caribbean islands in January I’m going on my own and was hoping to add Cuba, Aruba and Belize into the mix I was also considering Panama. I’m giving myself 6 months to go and see the beauties these islands have to offer. I was hoping to use ferries a lot and just book hotels before I went to each island as I don’t want to give myself any time restrictions in one place. If I like somewhere and want to spend more time there I want to be free to do so.
    As a solo woman is there anything you feel I should be wary of? Did you need visa to get into any of the countries? I’ve made appointments for the jabs I’ll need. I was also wondering about phone signal and internet coverage.
    I have to say your blog was insightful and has given me lots of ideas on what to see. And I’m sure I’ll be using it as I travel as a little guide
    Im hoping the locals will have lots of suggestions of things I need to see. And I get to take part in some of the festivals and carnivals.
    Thank you for all the advice you have given in this blog…

    Reply
    • Hi Derri, I ma happy to hear you found the blog useful. 6 months for the Caribbean sounds awesome and yes you could probably easily add Panama as there are many flights with COPA connecting the Caribbean too. We travelled as 2 women and found the Caribbean safe, the only tip where to avoid is Santa Lucia at night at the Friday party (we didn’t go but have been warned) and if you go to Haiti read our blog on where to go and what to see. It always helps to ask a local for advice on safety.

      As for hotel bookings, this is how we travelled as well: we only bought flights and hotels a few days before to allow us to go with the flow. We probably most loved (and you might like to spend some time there) Dominican Rep., Cuba, and Grenada and we really liked Dominica island as it’s very green. We spent 3 weeks in Cuba (sorry no blogs this was a few years back) and really loved it there.

      You might also look into staying at Airbnb as often the host can recommend what to do and see. All the best.

      Reply
  • Hi girls! Love your blog and your adventures! Awesome spirit! I am at 71 countries myself and shooting for 100. And a dream of mine is the southern Caribbean or Windward islands. I would love to work myself from Antigua to Trinidad (or vice versa). Your blog is super inspiring so I am really getting into planning mode here. But what I am trying to figure out and can’t really find is a realistic itinerary and reasonable logistics for someone who (unfortunately) can not be back packing for several months. I am trying to get my head around is how long travel is between the islands (unless flying) and how long to stay on each one. In your expert opinion – what is a minimum, and a realistic, time frame – if not staying one week on each island? And logistically, is there one country/island that is too complicated, and the one to cut out if necessary? Again, I am thinking Antigua/St Kitts/Dominica + Barbados/St Lucia/Grenada/St Vincent + possibly Trinidad Tobago. Would love your quick thoughts on this. Thank you so much! Daniel

    Reply
    • Hi Daniel, you could visit those islands in a month easily. The flights are usually just over an hour but as mentioned they are not connected by ferries so flying is the best way to get around. Overall 2-3 days can be enough to get a good taste of each island… laying on the beach for a week can be done on most of them but one of the best ways is to rent a car and explore the island for a day and then spend the next day doing something unique. Maybe check the website flight connections.com to see all current flight routes and try to piece your puzzle – it’s part of the fun. Hope this helps.:)

      Reply
  • Great blog, helped me understand better as I’m also planning to hit the 13 countries. However, I’m a digital Nomad and am depending on internet. How was the connection there? Was it easy to get sim cards with good data? Perhaps you have some info about pricing? Thanks alot

    Reply
    • Hi Jeff,
      We’re glad you have found the blog to be helpful. We relied heavily on internet/Wifi in our accommodation providers during our travels in the Caribbean, as we found local SIM cards quite expensive. Suppose we had to do it all again. In that case, we’d probably buy this Airalo Regional eSIM for the Caribbean to stay connected and then perhaps source a local SIM once you arrive on an island that you’d like to stay longer on, to get access to more data.

      Reply

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