hello@headlandyachting.com Crewed yacht charters in the Virgin Islands, from people who’ve sailed them
Our new website opens in November 2026. We’re already planning charters for the 2026–27 season: tell us your dates and we’ll come back with yachts that are free.
- 15+years of Tommy’s captaining and managing charter yachts
- 12years Emma and Tommy have worked side by side on the boats
- 100+luxury charters Emma and Tommy have run together as yacht crew
A broker on your side
Headland Yachting is an independent charter broker, based in London with our hearts in the British Virgin Islands. We don’t own a fleet, so we can recommend any yacht available through the Caribbean’s central agents and tell you honestly which crews, chefs and weeks are worth it.
You’ll deal with the two of us from your first message to the day you step ashore.
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Emma
Co-founder and charter broker
A dive instructor and professional yacht chef who went on to run luxury crewed charters across the Caribbean. Member of the Virgin Islands Professional Charter Association.
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Tommy
Co-founder and yacht charter specialist
More than 15 years captaining and managing yachts, many of them in the Caribbean. Commercially endorsed RYA Yachtmaster and former RNLI lifeboat trainer.
Tell us about your charter
A few words is plenty. We’ll reply by email, or with a call if you’d prefer.
No booking or payment is taken here, and an enquiry doesn’t commit you to anything.
Or email hello@headlandyachting.com
We use your details only to reply to your enquiry and help plan your charter. Our privacy policy explains how we look after them.