Choose an island for the holiday you want to have, then choose the accommodation. A beach-focused stay, time in historic towns and an active trip on land or water call for different bases. This directory brings together our existing Caribbean guides, with clear routes into each island's more detailed planning information.
Choose a starting point
Aruba
Beach time and an island base
Explore the guide to compare beach areas and the experiences you want beyond your hotel. Choose a location that matches how often you plan to go out.
Jamaica
Beaches, culture and a broader island trip
Use the overview to decide whether your trip stays in one area or includes more of the island. Plan the journeys before reserving several bases.
Bahamas
An archipelago rather than one interchangeable stop
Choose the island or islands first. Airport access and onward travel belong in the same decision as the accommodation and beach you prefer.
Browse all Caribbean guides
Choose a country for the wider picture, or open a city, island or regional guide for a more focused starting point.
Island and archipelago guides
Find the right trip for you
These are editorial starting points, rather than rankings or fixed itineraries. Use the linked destination guides to narrow your choice.
| Your priority | Where to start | First planning decision |
|---|---|---|
| A stay centred on the beach | Aruba, Bahamas or Cayman Islands | Compare the particular beach area and airport transfer. |
| Culture alongside coastal time | Cuba, Jamaica or Puerto Rico | Decide how city or town visits fit with your base. |
| Several places in one island trip | Dominican Republic or the Virgin Islands | Check which locations and connections the route actually requires. |
Turn your shortlist into a route
Treat these comparisons as starting points, not rankings: each destination offers more than one kind of trip. Read the relevant guide, then compare the specific base and transport you would use. An island-hopping plan can require more travel than the map suggests, while a single well-chosen base can leave more time for the beach, food and local experiences.
- Choose the island before comparing hotels across the whole region.
- Check weather and travel advice for the specific destination and dates.
- Compare transfers, meals and any onward island travel as part of the total holiday plan.
Caribbean planning questions
Which Caribbean island is best for a first visit?
There is no single best choice. Start with your preferred balance of beach time, culture and activity, then compare the guides and the practical journey from your departure airport.
Does this directory distinguish the US and British Virgin Islands?
The Virgin Islands guide covers the destination grouping. Check the specific islands, border arrangements and transport for your intended route rather than treating the group as one entry destination.
Plan your next step
Once you have chosen a destination, open its guide for the detailed trip plan. Compare places to stay, use our travel tips for practical preparation, or browse planning tools to organise the journey.