We’ve crewed the yachts we now recommend

Headland Yachting was founded by Emma and Tommy, who met as professional yacht crew in the British Virgin Islands more than a decade ago. Now they use what they learned on board to find each client the right yacht, crew and islands.

Our story

Emma and Tommy met as yacht crew in the British Virgin Islands and went on to run more than 100 luxury charters together, from the Virgin Islands to Grenada, the Bahamas and Florida. Along the way they were twice runner-up for Best Boat in Show.

Having worked every part of life on board, they know a great charter is about more than the yacht: it’s the right yacht, crew and islands for each party. That’s what Headland Yachting does.

The founders

Emma, smiling, at a marina with superyachts behind her

Emma

Co-founder and charter broker

Emma’s love of the sea started on the South Coast of England, and took her as far as Australia’s Whitsunday Islands aboard the racing yacht Matador.

In 2013 she arrived in the British Virgin Islands, fell for the islands and qualified as a PADI Dive Instructor. After a summer at a sailing camp she became Chief Dive Instructor on a 100-foot charter yacht, discovered the luxury charter world, and trained as a professional yacht chef.

Over the following years she ran luxury crewed charters throughout the Caribbean, won recognition in culinary and cocktail competitions, and developed an eye for the small things that make a week memorable. Having worked behind the scenes and with guests, she knows what sets an exceptional charter apart, and enjoys matching each client with the right yacht.

Emma is a member of the International Yacht Brokers Association (IYBA) and the Virgin Islands Professional Charter Association (VIPCA).

Tommy, smiling, on the deck of a yacht in a marina

Tommy

Co-founder and yacht charter specialist

Tommy has spent more than 15 years captaining luxury sailing and motor yachts and running charter operations in the Caribbean, the Bahamas, the United States, the Mediterranean and the UK.

Many of those years were in the British Virgin Islands, where he came to know the islands, anchorages and passages inside out. He also ran luxury yacht operations from Fort Lauderdale and skippered flotillas in Greece.

He holds a commercially endorsed RYA Yachtmaster and is a former RNLI lifeboat trainer: real seamanship, and a clear eye for how a yacht should be run and how guests should be looked after. He has worked alongside Emma for 12 years.

What our guests say

5.0 6 Google reviews Read them on Google (opens in a new tab)

Note: Example reviews. These are made up, to show how real reviews will look. They appear on this preview only and never on the live site.
  • Emma found us a catamaran with a crew who were brilliant with our three children, and she was honest about which weeks to avoid. Every detail was sorted before we landed.

    Sarah M.April 2026 · Family charter, BVI
  • We had no idea where to start. Tommy talked us through the islands on a call, sent a shortlist the next day and held our week while we decided. The chef was the highlight of the trip.

    James and Priya T.March 2026 · Honeymoon, BVI
  • Straight answers on costs, including the extras other brokers skipped. The yacht was exactly as described and the crew knew every anchorage.

    Rob K.February 2026 · Friends’ trip, BVI and USVI
  • They arranged a beach dinner for my birthday that I’ll never forget. Knowledgeable, warm and quick to reply, even across the time difference.

    Helen D.January 2026 · Fiftieth birthday
  • Good advice on which bareboat suited our sailing experience, and a useful briefing on moorings and customs before we went.

    Marcus L.December 2025 · Bareboat, BVI
  • Three generations on one yacht and everyone happy. Emma matched us with a crew who planned each day around Grandma and the grandchildren.

    The Okafor familyNovember 2025 · Multi-generation charter

How we work

  • Independent. We don’t own or manage yachts, so we can recommend any yacht through the Caribbean’s central agents, and tell you honestly what we think of it.
  • No surprises. When you’ve chosen, we ask the central agent to hold your week. Your charter is confirmed when you’ve signed the contract and paid the deposit.
  • The same people throughout. You’ll deal with us from your first enquiry to the day you step ashore.

The company

Headland Yachting Limited is registered in England and Wales, company number 17532233. Registered office: 128 City Road, London, EC1V 2NX.

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