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.
“We had an amazing tour with Undiscovered Destinations, island hopping in the Caribbean. We were wanting to visit the Caribbean but didn't want to go on a cruise ship. This small group tour was simply fantastic. We had some great local guides, that were very passionate about sharing their island home. Our accommodation was excellent and situated in convenient locations.”
Kelkat
Caribbean Island
“An amazing trip! We had the most amazing holiday — over two weeks we had a taste of the cities, the culture, the mountains, a safari, and time at the beach. Our driver/guide made the whole trip very relaxing, and we were welcomed warmly by everyone we met, enjoying fabulous food and drink along the way. Undiscovered Destinations planned a really amazing itinerary for us with great hotels, a fabulous guide/driver, and interesting places to visit — they took great care to ensure we had an excellent holiday. We look forward to booking another holiday with them in the future. Thank you, Mark!”
Anna
“This adventure was always going to be very full-on, which is how we like our trips. I didn't count on getting bronchitis and ending up in hospital, however. The itinerary was quickly amended to avoid high-altitude destinations as much as possible while still making sure we had a chance to enjoy interesting experiences. While obviously sad to have missed some of the original sites, the revised itinerary was the only sensible option under the circumstances. I was extremely impressed with how Undiscovered Destinations and their local team handled the situation — taking the stress out of it, smoothing the way, rearranging the itinerary and booking new hotels, translating for me with the medical staff, and making sure I always had transport, medicines and anything else I needed. Nothing was too much trouble, and they kept in touch with me, each other, and the insurance company throughout. I can't recommend them enough!”
Grete
“My wife and I had a wonderful tour with Undiscovered Destinations. We had a different guide at each stop, and all of them were friendly, cheerful and knowledgeable. The local people were welcoming, and we always felt safe and comfortable. The beaches were spectacularly beautiful and empty of people, with warm, clear water, and each stop had its own character — some we loved for their unspoiled scenery, others for their history and the warmth of the welcome. We took the opportunity to snorkel on one of the most pristine reefs we've experienced, swimming with sea turtles and enormous manta rays that came right up to us out of curiosity. A wonderful destination for nature lovers.”
Frank
“Excellent. Action packed. Our local agent was excellent, and a good choice by Undiscovered Destinations. Because there were only two of us on the holiday, we had different guides at each stop, each one making sure we were handed over safely. All manner of transport was used, and we appreciated the different guiding strategies, the wealth of information given, the high level of English, and the genuine wish to show off their country at its best. Excellent.”
Cathy
“Far exceeding my expectations, this was one of the best trips I've ever done. A beautiful destination, with interesting history, lively ceremonies, lovely people and — surprisingly, for somewhere that sees so few tourists — absolutely no hassle on the streets. Excellent service from start to finish, with a first-class tour leader.”
Lynn
“We had a two-week trip with Undiscovered Destinations, flying in for two days first to break up the journey. It was a great trip, because we managed to see so much more than just the capital cities. This was the fourth trip we've taken with Undiscovered Destinations, and each one has been wonderful. Our guides were lovely — very professional and helpful. We rate UD very highly.”
Andy
“We had a fabulous trip with an excellent local guide, who took great care of us and enthusiastically shared his knowledge of both ancient and recent history, with lots of fascinating personal stories of his own life. We highly recommend this trip — Undiscovered Destinations were great to work with, and we hope to use them again.”
Jennie
“Everything was great — we got to witness a wonderful variety of wildlife, and thoroughly enjoyed the scenery and the hospitality of the people. A fabulous trip from start to finish.”
Debbie
“Excellent all-round trip. Drivers were conscientious and careful, accommodation was better than expected, and the scenery was stunning throughout.”
Alexis
“We had an amazing tour with Undiscovered Destinations, island hopping in the Caribbean. We were wanting to visit the Caribbean but didn't want to go on a cruise ship. This small group tour was simply fantastic. We had some great local guides, that were very passionate about sharing their island home. Our accommodation was excellent and situated in convenient locations.”
Kelkat
Caribbean Island
“An amazing trip! We had the most amazing holiday — over two weeks we had a taste of the cities, the culture, the mountains, a safari, and time at the beach. Our driver/guide made the whole trip very relaxing, and we were welcomed warmly by everyone we met, enjoying fabulous food and drink along the way. Undiscovered Destinations planned a really amazing itinerary for us with great hotels, a fabulous guide/driver, and interesting places to visit — they took great care to ensure we had an excellent holiday. We look forward to booking another holiday with them in the future. Thank you, Mark!”
Anna
“This adventure was always going to be very full-on, which is how we like our trips. I didn't count on getting bronchitis and ending up in hospital, however. The itinerary was quickly amended to avoid high-altitude destinations as much as possible while still making sure we had a chance to enjoy interesting experiences. While obviously sad to have missed some of the original sites, the revised itinerary was the only sensible option under the circumstances. I was extremely impressed with how Undiscovered Destinations and their local team handled the situation — taking the stress out of it, smoothing the way, rearranging the itinerary and booking new hotels, translating for me with the medical staff, and making sure I always had transport, medicines and anything else I needed. Nothing was too much trouble, and they kept in touch with me, each other, and the insurance company throughout. I can't recommend them enough!”
Grete
“My wife and I had a wonderful tour with Undiscovered Destinations. We had a different guide at each stop, and all of them were friendly, cheerful and knowledgeable. The local people were welcoming, and we always felt safe and comfortable. The beaches were spectacularly beautiful and empty of people, with warm, clear water, and each stop had its own character — some we loved for their unspoiled scenery, others for their history and the warmth of the welcome. We took the opportunity to snorkel on one of the most pristine reefs we've experienced, swimming with sea turtles and enormous manta rays that came right up to us out of curiosity. A wonderful destination for nature lovers.”
Frank
“Excellent. Action packed. Our local agent was excellent, and a good choice by Undiscovered Destinations. Because there were only two of us on the holiday, we had different guides at each stop, each one making sure we were handed over safely. All manner of transport was used, and we appreciated the different guiding strategies, the wealth of information given, the high level of English, and the genuine wish to show off their country at its best. Excellent.”
Cathy
“Far exceeding my expectations, this was one of the best trips I've ever done. A beautiful destination, with interesting history, lively ceremonies, lovely people and — surprisingly, for somewhere that sees so few tourists — absolutely no hassle on the streets. Excellent service from start to finish, with a first-class tour leader.”
Lynn
“We had a two-week trip with Undiscovered Destinations, flying in for two days first to break up the journey. It was a great trip, because we managed to see so much more than just the capital cities. This was the fourth trip we've taken with Undiscovered Destinations, and each one has been wonderful. Our guides were lovely — very professional and helpful. We rate UD very highly.”
Andy
“We had a fabulous trip with an excellent local guide, who took great care of us and enthusiastically shared his knowledge of both ancient and recent history, with lots of fascinating personal stories of his own life. We highly recommend this trip — Undiscovered Destinations were great to work with, and we hope to use them again.”
Jennie
“Everything was great — we got to witness a wonderful variety of wildlife, and thoroughly enjoyed the scenery and the hospitality of the people. A fabulous trip from start to finish.”
Debbie
“Excellent all-round trip. Drivers were conscientious and careful, accommodation was better than expected, and the scenery was stunning throughout.”
Alexis
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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