Experience the Caribbean with our expertly guided small group tours. Our Caribbean Island Tours showcase the region’s most beautiful islands, combining cultural discovery, natural highlights, and time to relax on some of the world’s finest beaches.
The Caribbean is an archipelago of extraordinary variety — volcanic peaks, rainforests, colonial towns, and some of the most beautiful beaches on earth. Each island carries its own distinct character, shaped by centuries of African, European, and indigenous influence, with warm seas and vibrant cultures that draw travellers back time and again. From the lush "Nature Isle" of Dominica to the Dutch-colonial streets of Curaçao, the Caribbean rewards those who look beyond the resort.
Our small group Caribbean Islands tours take you island-hopping by regional flight and catamaran rather than cruise ship, so you spend more time exploring and less time queuing. Over 20 days, Caribbean Island Hopping visits St. Kitts & Nevis, Antigua, Dominica, Saint Lucia, Saint Vincent, Trinidad, Curaçao, and Aruba — with a maximum of 12 travellers, expert guides, and a pace that lets you genuinely discover each island.
Caribbean Island
Small-group departures led by local experts, plus private tailor-made itineraries shaped around your interests, pace and dates.
Eight very different islands — volcanic rainforest, Dutch colonial towns, desert national parks, and coral reefs — visited without ever boarding a cruise ship. This is Caribbean island hopping on your own terms.
A maximum of 12 travellers means you move at a human pace, access places cruise passengers don't reach, and share your experience with a group small enough to feel like friends.
From Brimstone Hill Fortress in St. Kitts to Morne Trois Pitons National Park in Dominica, the Caribbean holds remarkable heritage that goes far beyond beaches.
The Dutch Antilles — Curaçao and Aruba — remain little-visited by British and American travellers. For those who think they know the Caribbean, these islands offer a genuine surprise.
See itinerariesCaribbean Island rewards travellers who slow down — the best stories are found off the tour-bus route.
From the field
The Caribbean has two broad seasons. The dry season runs from roughly December to April, bringing sunshine, lower humidity, and reliably calm seas — ideal conditions for exploring on foot and on the water. May to November is the wet season, when afternoon showers are common and the Atlantic hurricane season is active, peaking between August and October. Temperatures throughout the year are warm, typically in the mid-to-high 20s°C, with cooling trade winds making the heat comfortable across most islands.
Our Caribbean Islands tours depart in February — comfortably within the dry season — offering bright, settled weather across St. Kitts & Nevis, Antigua, Dominica, Saint Lucia, Saint Vincent, Trinidad, Curaçao, and Aruba.
Looking to travel outside the typical windows? Our Caribbean Island tailor-made team can advise on the best time for you.
Dispatches, field notes and practical advice from our specialists.
Reviews from across our small-group programme. Independently rated 4.9 Excellent on AITO by 250+ travellers.
Every one of our Caribbean Island journeys can be rebuilt around your dates, pace and interests — or we’ll design something entirely new.
We’ll build one around you.
The Caribbean's island diversity makes it exceptionally well-suited to a tailor-made approach — different islands reward very different types of traveller, and the right combination depends entirely on your interests and travel style. A private itinerary might focus on the volcanic drama of Dominica and Saint Lucia, linger longer in the Dutch Antilles for Curaçao's art and food scene, or combine mainland Trinidad's wildlife with Aruba's desert landscapes at a pace that suits you. Private travellers can also choose their own travel window, avoiding the peak February season if preferred, with access to private transport, local guides, and a broader range of accommodation. Speak to the Undiscovered Destinations team and we'll design a Caribbean island package built around what you want to see.
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Our Caribbean Islands tour packages start from £9,950 per person, based on two sharing. This includes accommodation throughout, all inter-island flights and ferry transfers, guided excursions, entrance fees, and most breakfasts. A single room supplement of £1,995 applies for solo travellers who prefer their own room.
Shared across all tours that visit this destination. Read alongside your individual tour dossier for trip-specific details.
We constantly monitor official travel advice, including the UK Foreign, Commonwealth & Development Office (FCDO) Caribbean Islands Travel Advice, and will always advise clients of any warnings before departure. As this tour visits multiple island nations, we monitor the FCDO advice page for each country individually — including St. Kitts & Nevis, Antigua & Barbuda, Dominica, Saint Lucia, Saint Vincent & the Grenadines, Trinidad & Tobago, and the Netherlands (for Curaçao and Aruba). At the time of writing, there are no specific warnings against travel to the islands we visit on our tours.
Please contact us if you have any specific concerns or would like to understand what measures are in place to ensure your trip remains safe and trouble-free.
Join a small-group departure, or let our Caribbean Island specialists craft a private journey shaped around your dates and interests.
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