Our story
Born from a love of the Caribbean
Island Escapes was founded by two travellers who fell hopelessly in love with the Caribbean — and never stopped going back.
14+
Years specialising in the Caribbean
4,800+
Holidays crafted
98%
Client satisfaction rate
30+
Islands we know intimately
How it all began
In 2009, James and Claire Henderson took a two-week holiday to Barbados. They expected a nice break. What they got was a life-changing obsession. The warmth of the people, the extraordinary variety of the islands, the food, the music, the colours — they were completely captivated.
Back in London, they found that no travel company truly specialised in the Caribbean with the depth of knowledge they craved. Most treated it as just another sun destination. James and Claire knew it deserved far better.
In 2012, they left their careers in finance and marketing, and founded Island Escapes. The mission was simple: to share their passion for the Caribbean with travellers who wanted more than a package holiday — who wanted a genuine, expertly crafted experience.
Why we only do the Caribbean
We could have built a general travel company. We chose not to.
Unmatched depth of knowledge
By focusing exclusively on the Caribbean, our team has visited every island we sell — many of them dozens of times. We know the best villas, the hidden beaches, the local restaurants that don't appear in any guidebook.
Genuine passion
We're not selling a product — we're sharing a love affair. Every itinerary we create is one we'd happily take ourselves. That passion comes through in every detail.
Trusted local relationships
Over 14 years, we've built deep relationships with the best hotels, villa owners, and local guides across the Caribbean. These connections mean our clients get access, upgrades, and experiences that simply aren't available elsewhere.
Tailored to you
No two Caribbean holidays are the same. Whether you're a honeymooning couple, a multi-generational family, or a solo adventurer, we craft every trip around your exact wishes.
Meet the team
Every member of our team has lived and breathed the Caribbean. When you call us, you speak to someone who has actually been there.
James Henderson
Co-founder & Caribbean Director
James has visited over 25 Caribbean islands and considers Barbados his second home. He leads our destination strategy and personally oversees every luxury and honeymoon itinerary.
Claire Henderson
Co-founder & Client Experience Director
Claire's background in luxury hospitality means our clients receive an exceptional level of care from first enquiry to final return. She is obsessed with the details that make a holiday unforgettable.
Sarah Okafor
Senior Caribbean Specialist
Sarah joined us in 2016 after spending three years living in Jamaica. Her knowledge of the island's culture, food, and hidden gems is unrivalled. She also specialises in St Lucia and Grenada.
Marcus Webb
Family & Adventure Specialist
Marcus has taken his own family to the Bahamas, Turks & Caicos, and Antigua multiple times. He designs our family packages and multi-generational itineraries with the insight only a parent can bring.
Priya Sharma
Luxury & Honeymoon Specialist
Priya has an encyclopaedic knowledge of the Caribbean's finest resorts and private villas. She has personally inspected over 200 properties and is the person to speak to for a truly special occasion.
Ready to start planning?
Whether you have a destination in mind or simply know you want the Caribbean, we'd love to help you create something extraordinary.
Get in touch