The Virgin Islands, by yacht

Crewed and bareboat charters in the British and US Virgin Islands, arranged by a broker who knows the boats, the crews and the anchorages.

A broker on your side

We match you with the right yacht and crew ourselves, because the people aboard make the charter.

We’re independent of every fleet, so we can recommend any yacht in the islands and tell you honestly which crews, chefs and weeks are worth it.

About Headland Yachting

  1. Tell us about your party

    Who’s coming, when, and how you like to spend a holiday. A short form or a call is all it takes.

  2. We shortlist and hold

    We come back with yachts that are free on your dates, and ask the central agent to hold your favourite while you decide.

  3. Confirm and look forward

    You sign the charter contract and pay the deposit. We look after the details until you step aboard.

A few of the yachts

See every yacht

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

Charter advice

All articles

Charter notes from the islands

A short email now and then: yachts with a free week, offers from the crews we trust and the best of the season in the Virgin Islands.

Now and then, never shared, and you can unsubscribe from any email. How we use your data.

Questions we’re often asked

How far ahead should we book?

For Christmas, New Year and Easter, nine to twelve months ahead: the best yachts go first. For other weeks, three to six months is usually enough, and we can sometimes find a yacht at shorter notice.

What does a crewed charter cost, all in?

Most crewed yachts in the Virgin Islands have a weekly rate that includes the crew, meals and most drinks. On top come a crew gratuity, usually 15 to 20 per cent, and sometimes cruising permits or fuel. We show you the likely total before you book. More in our guide to contracts and deposits.

Do we need any sailing experience?

Not for a crewed charter: the captain and crew sail the yacht and you simply enjoy it. For a bareboat charter, someone in your party needs to skipper, and we can arrange a paid skipper if you’d rather not. See crewed or bareboat?

Tell us about your charter

Dates, guests, the kind of week you have in mind. We’ll reply within one working day with yachts that are free.

Start an enquiry hello@headlandyachting.com

Send feedback

It goes straight to the team building the site, with this page’s address.

What’s it about?

Page: