How many travellers will be in my group?

Maximum 12 travellers — that's the cap on every Undiscovered Destinations small-group tour. Small enough to eat in a local family home; large enough to share the wonder with other like-minded travellers.

Yes — there's no compulsory single supplement on our small-group tours. You get your own room at no extra cost. About 60% of UD travellers come solo, so you'll be in good company.

How fit do I need to be?

Fitness requirements vary by itinerary, from gentle to demanding. The day-by-day tour dossier sets out walking distances, terrain and any altitude so you know what to expect. If you have specific concerns, speak to our team before booking — they can talk you through a typical day.

When are the next departures?

The next available departures are 16 February 2027; 17 February 2028. See the "Choose your departure" table further up the page for the full schedule and per-departure pricing.

What's included in the tour price?

Included items vary by tour — see the full list above. On this trip, expect: Arrival and departure transfers; Minibus, or similar vehicle for guided excursions and tours; All inter-island economy class flights including a checked-in luggage allowance of 20k; and more. International flights and travel insurance are not included.

Where exactly does this trip go?

This tour visits Caribbean Island. Each destination has its own page with practical information, climate, and the attractions our specialists recommend — linked from the itinerary above.

Caribbean Island20 daysMax 12 travellersSolo-friendly

Caribbean Island Hopping

Explore eight stunning Caribbean islands — from Dominica's volcanic rainforests and Saint Lucia's UNESCO Pitons to Aruba's rugged national park — in a small group of no more than 12 travellers.

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About this journey

What to expect on this trip

A unique opportunity to island hop between some of the most beautiful destinations on earth. And rather than joining thousands of other travellers on a cruise ship the size of a small town, our small group will use the network of regional flights to reach our next destination giving you more time to explore.

Our adventure starts in St Kitts where we take a luxury catamaran to its sister island Nevis with the chance along the way to snorkel and view the rich marine life. Next stop is Antigua where we explore the bustling capital of St John’s, with its salty-glamorous English Harbour, and historical forts and other vestiges of the colonial past. Our next hop takes us south to little-known rainforest islands like Dominica where we explore lush rainforests and natural hot springs which justifies the country’s status as the “Nature Island”. We reach our next destination not by flying, but by taking the local ferry to Saint Lucia where we explore the island including the one-of-a-kind Sulphur Springs and the world’s first drive-in Volcano.

Back in the air we continue our adventure with a short flight to St Vincent and the Grenadines – a place that evokes visions of exotic, idyllic island life. Imagine an island chain in the heart of the Caribbean Sea, uncluttered by tourist exploitation, with white-sand beaches on deserted islands, sky-blue water gently lapping the shores and barely a soul around. Next stop is Trinidad and Tobago, where we discover the country’s cultural and religious diversity before taking a well-earned break and enjoy a ‘free day’ to unwind and recharge before we head to the Dutch Antilles for the final leg of our trip.

With its delightful Dutch colonial architecture, thriving art and culinary scenes and excellent history museums, Curacao feels like a little piece of Europe at the edge of the Caribbean. A short hop takes us to our final destination, Aruba, where we mark the end of our adventure by travelling by off-road vehicle across the rugged terrain of Arikok National Park.

The journey

Caribbean Island Hopping

What makes this trip special

Drawn from the full tour dossier — the standout days, encounters and views our specialists keep coming back to.

Your route

The highlights

Volcanic Wonders and Natural Landscapes
From Dominica's UNESCO Boiling Lake and Trafalgar Falls to Saint Lucia's Pitons, geothermal fields, and hot springs, this tour immerses travellers in the raw volcanic drama of the Eastern Caribbean. Arikok National Park in Aruba and Shete Boka's wave-carved caverns in Curaçao add further geological spectacle to an already extraordinary natural itinerary.
Caribbean History and Colonial Heritage
Eight islands means eight distinct layers of colonial history, from the British-built Nelson's Dockyard in Antigua and Fort Charlotte in Saint Vincent to Trinidad's 'Magnificent Seven' mansions and the Dutch-colonial streets of Willemstad and Oranjestad. The Wingfield Estate Sugar Plantation Ruins in St. Kitts offer a vivid and sobering glimpse into the region's plantation past.
Beach, Sea, and Island Life
Every island on this itinerary brings its own stretch of coastline, from the white sands of Pinney's Beach in Nevis and Buccament Bay in Saint Vincent to the crystal-clear waters at Grote Knip in Curaçao. Catamaran sailing with snorkelling, swimming in natural volcanic rock pools, and open-bar beach days ensure the Caribbean's most iconic pleasures are woven throughout the journey.
Guided Island Tours with Local Experts
Each island is explored with an experienced local guide who brings specialist knowledge of history, ecology, and culture to every stop on the itinerary. Flexible, full-day excursions in Dominica, Saint Lucia, Saint Vincent, and Curaçao go well beyond the standard tourist trail, revealing lesser-visited landscapes and authentic local character.
Culture, Cuisine, and Caribbean Diversity
Trinidad and Tobago's extraordinary cultural melting pot — African, Indian, Creole, and European — contrasts with the Dutch Caribbean identity of Curaçao and Aruba, creating a genuinely varied cultural journey across the region. The tour includes time on Ariapita Avenue in Port of Spain and the flamingo-pink streets of Willemstad, giving travellers space to absorb each island's unique flavour.

Full itinerary · 20 days

Free — no sign-up

Dates & prices

Choose your departure

Reserve your place with a £1,220 per-person deposit; the balance is due 70 days before departure. Prefer your own space? A single room is available on every departure.

Departs	Returns	Status	Price pp	Single supp.
16 Feb 2027	7 Mar 2027	Guaranteed	£9,950	+£1,995	Book now
17 Feb 2028	7 Mar 2028	Guaranteed	£10,945	+£1,995	Book now

Departure
16 Feb 2027 → 7 Mar 2027
Guaranteed
From
£9,950 pp
Single supp. +£1,995
Book now
Departure
17 Feb 2028 → 7 Mar 2028
Guaranteed
From
£10,945 pp
Single supp. +£1,995
Book now

Can’t find the right fit?

Every one of our Caribbean Island journeys can be rebuilt around your dates, pace and interests — or we’ll design something entirely new.

Tailor my trip

What's included

What your tour price covers

Included in the price

Arrival and departure transfers
Minibus, or similar vehicle for guided excursions and tours
All inter-island economy class flights including a checked-in luggage allowance of 20k
Ferry travel from Dominica to Saint Lucia
All accommodation
Experienced local guide for all excursions and tours
Services of an English-speaking tour leader – applicable for groups of 5 or more travellers (groups of less than 5 will travel unescorted between each island)
Meals as listed
Entrance fees for sites listed as part of the itinerary

Budget separately for

International flights (, contact , us, for expert advice and a quote)
Any airport taxes (except when included with regional flights)
Travel Insurance
Visa – when required
Drinks
Items of personal nature
Tips (Discretionary)

Before you go

Essential information

Shared across all tours that visit this destination. Read alongside your individual tour dossier for trip-specific details.

Foreign Office travel advice

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.

Voices from the road

What travellers say about us

Independently verified reviews from travellers who joined Caribbean Island Hopping. Rated 4.9 Excellent on AITO by 250+ reviewers.

“Olaf was fantastic. Very responsive to our group's needs and made transfers between airports very easy. He is well travelled, organised and calm. He was able to be flexible when required. We loved the accommodation we stayed in. Perhaps the only "complaints" (minor) was the size of the room we had in Curaçao and the breakfast at the Copper and Lumber Hotel was very basic. Out of all the places we visited, we were a bit disappointed with Aruba. It was like a state of the USA and it felt like an on-land cruise boat. It didn't have the Caribbean vibe we had experienced elsewhere and because of this, felt we stayed too long at that location. It would be better to reduce the time in Aruba and include somewhere like Tobago, Barbados or Grenada. ”

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Kath Kelly, Australia

“It was a wonderful opportunity to explore a string of islands with different cultures and histories.”

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Nigel Branscombe, UK

“Caribbean Island trip was been fabulous, and your guide, Olafs Stals is terrific! Great memories, very good & balanced itinerary.”

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George Boyd, Spain

“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.”

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Kelkat

“Jason was very helpful and the booking process was quick and easy. UD offers itineraries that many competitors do not. I thoroughly enjoyed both trips I've taken with them. While they may not suit everyone, I have happily recommended the Senegal tour to fellow travellers.”

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Bernice Hird, UK

Helped by Jason van der Wath

“Excellent customer service, reliable itineraries and ability to solve local issues when they arise”

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Gustavo Musto, Uruguay

“I like the small size of groups, the range of destinations and excellent itineraries. This is my third holiday with your company and I have found your itineraries really good.”

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Traveller from the UK

“Excellent company to book with. Complex tour mostly delivered as per itinerary with professional and pleasant local representatives. ”

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Adam Choonara, UK

“I really appreciated Jason's help in answering all of my many questions re: Senegal trip in December 2025. I have a physical disability and I had a lot of accessibility questions for Jason! He was a true professional and was very supportive, warm and friendly and helped me a lot in making my decision to go ahead with the Senegal trip. I would like to thank Jason particularly for this service. I truly appreciate it and I am very thankful.”

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Ramnit Bassi, UK

Helped by Jason van der Wath

“Undiscovered Destinations is able to find wonderful support staff and will go to the far corners of the earth.”

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Patricia Taylor, UK

Want to customise this tour?

Make Caribbean Island Hopping your own — adjust the route, dates, pace or who travels, or start from a blank page with a specialist. We'll bring the details of this trip straight into your enquiry.

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