Our Caribbean travels went far beyond a conventional beach holiday. We lived in Martinique and used it as a base to island-hop around the wider region — experiencing French Caribbean culture, rainforest islands, extraordinary beaches, music, food, road trips and very different personalities from one island to the next. The Caribbean is not one destination. It is dozens of them, and no two of the eight we've explored feel remotely alike.
Living in Martinique gave us the chance to experience Caribbean life beyond a normal holiday. Instead of a week in a resort, we had a base — the Island of Flowers — from which to properly get to know the wider region, one island at a time.
What struck us most was how different neighbouring islands can be, sometimes after only a short ferry ride or a quick flight. French, British, Dutch and independent Caribbean influences all sit within easy reach of one another, and each brings its own language, food, music and pace of life. Martinique and Guadeloupe feel distinctly French. Anguilla and Dominica feel distinctly their own. Sint Maarten and Saint Martin manage to be two countries on one small island. Jamaica is its own world entirely.
Where transport allowed, we travelled by ferry or short flight rather than sticking to package tours, and we tried to discover places independently — hiring cars, stopping wherever looked interesting, finding beaches and villages and bars that most visitors staying in a single resort would never see. That approach is what made our Caribbean travels so memorable, and it's the thread running through every one of the guides below.
Martinique was our Caribbean base, and from there we explored a string of very different islands across the region. This map is about the places themselves rather than forcing them into one continuous route. Tap an island to jump straight into its guide.
Our home in the Caribbean, and the base for everything else on this page — a year of sun, sea, tropical storms and the friendliest people we've met.
Read the full guide →Gustavia, superyachts and exploring independently — a small island with a very particular, very French Caribbean character.
Read the full guide →The Jazz Festival, Steven Seagal on stage, the Gros Islet street party and the extraordinary Pitons rising straight out of the sea.
Read the full guide →Maho Beach and Grand Case — Dutch and French sides of the same small island, each with a completely different feel.
Read the full guide →Renting a car from the ferry terminal with no real plan — hidden beaches, tiny villages, reggae bars and, unforgettably, the island's famous free-range chickens.
Read the full guide →A butterfly-shaped French island of beaches, rainforest trails and an active volcano — a genuinely varied landscape in one destination.
Read the full guide →The wild side of the Caribbean — winding rainforest roads, waterfalls and a landscape that feels a world away from a typical beach island.
Read the full guide →Music, energy and personality — our time in Montego Bay and Negril and everything that made Jamaica stand apart from the rest of the region.
Read the full guide →The Caribbean gets treated as one homogeneous destination far too often. Here's how our eight guides actually break down.
Seven quick questions, based on the eight islands we've actually explored.
If you'd rather combine several Caribbean stops in one itinerary, these multi-island TourRadar trips are worth a look. We haven't taken these exact tours ourselves, but they offer an easy way to compare longer and shorter Caribbean journeys.
A longer Caribbean itinerary that includes several places featured in our own guides, including St Lucia, Guadeloupe/Îles des Saintes, St Barths, Sint Maarten and Anguilla.
View the 22-day voyage →A mid-length multi-island option for travellers who want to see more of the region without committing to a three-week itinerary.
Explore the 15-day itinerary →The shortest of the three options — a useful choice if you want a multi-stop Caribbean trip within a more compact timeframe.
Explore the 8-day itinerary →Disclosure: These are affiliate links. If you book through them, we may earn a small commission at no extra cost to you.
A handful of practical things worth knowing before island-hopping around the region. Requirements and conditions change, so always check the latest information for your specific destination before you travel.
The Euro is used in the French territories, the US and Eastern Caribbean dollars are common elsewhere, and Jamaica has its own currency.
French in Martinique, Guadeloupe, St Barths and Saint Martin; English across most of the rest of the islands we've visited, with Dutch also spoken in Sint Maarten.
French, British, Dutch and independent Caribbean nations all sit within the region, each with their own rules, currency and administration.
Requirements differ by island and can change — always check the current entry requirements for your specific destination before travelling.
Some neighbouring islands are connected by short ferry crossings, while others need a flight — transport links vary a lot across the region.
Tropical weather and hurricane season run roughly from June to November — worth factoring into when you plan to travel.
Which side of the road you drive on, licence requirements and road conditions all vary from island to island.
Pace of life, food, music and everyday culture change dramatically as you move between islands, even ones close together.
One of the things our Caribbean travels made clear is that there is no single "Caribbean food" — the region's cuisine and culture change island to island. In Martinique, Guadeloupe and St Barths, French influence runs through everything, from the food to the language to the general atmosphere, alongside distinct Creole traditions of their own. Move to Anguilla, Dominica, St Lucia or Jamaica and the flavours, music and pace of life shift again, shaped by British, independent and other Caribbean traditions.
That contrast — French-Caribbean sophistication one island over from rainforest villages or reggae-filled beach bars — is part of what made exploring the region so rewarding. It's a theme that runs through each of our individual guides above.
Common questions
Eight islands, eight completely different personalities, all shaped by the year we spent living in Martinique and exploring the region around it. Pick the one that matches what you're after and read the full story.