Sailing the Grenadines

The Grenadines are a chain of roughly thirty small islands and cays running south from St. Vincent for sixty nautical miles, ending at Petit Saint Vincent on the border with Grenada. Most are uninhabited. The handful that carry villages — Bequia, Canouan, Mayreau, Union Island — are small enough to walk across in an afternoon. What sits between them is the point: shallow, protected water in every shade of blue, reefs you can swim to from the deck, and anchorages where some nights you will share the bay with two other yachts and some nights with none.

It is, by most measures, the best cruising ground in the Caribbean. The islands are close together — the longest passage on a typical week is under twenty nautical miles — so the sailing is a series of comfortable reaches rather than long deliveries. The trade winds blow steady from the east-north-east, twelve to twenty knots through the season, which means you sail every day rather than motor. There is no commercial shipping to speak of. And the Tobago Cays Marine Park — five uninhabited cays behind a horseshoe reef — is the kind of place that does not really have an equivalent anywhere else in the islands.

We base our fleet at Canouan, in the geographic centre of the chain. That matters more than it sounds. From Canouan, every island worth sailing to is within a single comfortable day: the Tobago Cays at ten nautical miles, Mustique at fifteen, Mayreau at twelve, Union Island at sixteen, Bequia at twenty. A charter from the centre of the chain spends its time at anchor and under sail, not on long passages to and from a base at one end.

This guide covers what a charter actually looks like — the season, the route, the islands one by one, and the practical questions guests ask before they book. If you already know the Grenadines and simply want to talk dates, the enquiry button works from anywhere on this page. If you are still deciding whether this is the right cruising ground for your week, read on.

A note on how charters here divide. A day charter is a single day out of Canouan — six to ten hours, a route shaped on the morning of, back to the marina by evening. It suits guests staying ashore on Canouan or Mustique who want one day on the water, and it is the least expensive way to see the chain under sail. A term charter is a week aboard — seven nights at anchor across the islands, the yacht as the accommodation. It suits guests who want the Grenadines to be the holiday rather than an excursion from it. Both run on the same fleet, with the same crew, from the same marina.

The sailing itself is forgiving. The water is protected by the reefs and the islands, so the seas inside the chain are flat to moderate even when the trades are up. Distances are short. The hazards — the reefs — are well charted and, from the deck of a crewed yacht, somebody else's job to watch. It is a cruising ground that rewards first-time charter guests and seasoned sailors equally, which is not true of everywhere in the Caribbean.

What does not change between a day and a week is the kind of yacht and the kind of day. Our fleet is classic crewed sailing yachts — Cap II, a 77 ft CNB flagship; Flying Wing, a 75 ft classic; and SISU, a 37 ft entry yacht — each chartered privately, never by the seat, never sub-chartered out of region. The day is shaped around the guests aboard: where to anchor, how long to stay, when to sail. That is the Rex Sailing difference, and it is the same whether you are aboard for eight hours or seven nights.