St Martin, Anguilla and St Barts: The Leewards Triangle by Superyacht

Three islands sit close enough together in the northern Leewards that a week among them feels less like a voyage than a sequence of very different evenings. St Martin is two countries on one island, French and Dutch, with the busiest harbours and the best restaurants. Anguilla is flat, quiet and British, ringed with some of the whitest sand in the Caribbean. St Barts is the polished one, steep and French and small. The passages between them are short enough that the captain's main decision each morning is which one to wake up beside.

This guide is about that triangle as a week-long itinerary. If it is St Barts at the turn of the year you are after, our guide to New Year's in Gustavia covers that separately.

St Martin: One Island, Two Flags

The island has been shared between France and the Netherlands for centuries, and the border is an invisible line you cross without a checkpoint. The French side, Saint-Martin, runs along the north and east. The Dutch side, Sint Maarten, holds the south and the main airport. For a charter this is a practical advantage: you can provision, refuel and change crew on one side, then spend the evening on the other.

On the French side, Marigot has a working waterfront and a market, but the real draw is Grand Case, a single seafront street that has long been known for its kitchens, from small roadside grills called lolos to proper French dining rooms. Anchored off the village, the tender ride in at dusk is the point of the stop. Further south and east, Orient Bay is the island's long, lively beach, and just off it lies Pinel Island, a small cay with a calm anchorage and a reef to swim over.

On the Dutch side, Philipsburg faces Great Bay, a wide, easy anchorage with a boardwalk and shops behind it. Around the point, Simpson Bay has an enormous lagoon that shelters a large number of yachts, entered through bridges that open at set times, so any visit inside depends on your yacht's air draft and beam. Your captain will know whether it is worth the effort or whether you are better off at anchor outside. At the western end, the planes landing low over Maho Beach are a spectacle that sunbathers and yacht guests both turn out for.

Tintamarre and the Quiet East

Many first-time guests miss the best of St Martin's water because the island's reputation is social. Tintamarre, also called Flat Island, lies off the east coast, uninhabited and low, within the protected waters of the island's nature reserve. It is a morning of swimming, snorkelling and a long empty beach before the day trippers arrive. It is a day anchorage, with the Atlantic swell deciding whether it is comfortable, so treat it as a weather-permitting extra.

Anguilla: Short Hop, Different Mood

Anguilla lies just across a narrow channel to the north of St Martin, a short crossing that takes a fraction of a morning. It is a British Overseas Territory, so the yacht clears in formally, usually at Road Bay off the settlement of Sandy Ground, which has the island's main anchorage. Your charter team handles the paperwork in advance. It is worth building a little time into the day for it.

What Anguilla offers is space. The island is long, low and almost entirely beach, with few large buildings. Shoal Bay East is the famous stretch, a long arc of white sand with a reef close inshore. Meads Bay, on the west coast, is broader and more sheltered in the right swell. Off Road Bay, Sandy Island, a tiny cay with a few palms and not much else, is the picture-book beach that charter guests go to for lunch.

The offshore cays are where Anguilla earns a night or two. Prickly Pear Cays to the north-east and Dog Island further out are quiet, and good for snorkelling. They are open to weather, which is the honest caveat. Anchoring at either is a captain's call on the day.

St Barts: The Last Leg

From the north of St Martin it is an open-water passage of a few hours to Gustavia, with the Atlantic swell deciding the mood of the crossing. Expect the captain to choose the timing around the forecast, and expect a good lunch at the other end.

St Barts is the polished end of the triangle. Gustavia's harbour is small and tidy, the town compact, the shopping and dining dense for a village. Anchorages ring the island: Shell Beach within walking distance of the harbour, the long sand at Saint-Jean on the north shore, and Colombier at the north-west tip, which is reachable only by sea or on foot and is one of the loveliest places to spend a morning in the Leewards. Parts of the coast are protected marine reserve, so the days run more to swimming than to watertoys.

How the Week Flows

A week here rarely needs a tight plan. A common shape runs: the first nights around St Martin, a day on the French side at Grand Case and Tintamarre, then a morning crossing to Anguilla for a beach lunch at Sandy Island and a night off Road Bay or at the cays. The second half belongs to St Barts, with a couple of nights at Gustavia and Colombier, and a day spare for weather. The order can run in reverse, and the best itineraries are loose enough to be reshuffled by the forecast.

The caveat is that all three islands were hit by Hurricane Irma in 2017. Recovery has been substantial, but conditions and facilities ashore change, so ask your broker for current detail before you commit to a particular restaurant or beach club.

When to Go

The Caribbean season runs from roughly November to April, with the trade winds steady and the weather settled. Christmas and New Year carry premium rates and book far ahead, and St Barts in particular fills for that week. January, February and March are the calm part of the season, and it is when this triangle is at its easiest. June to November is hurricane season, and few charter yachts stay.

Chartering the Triangle

This is one of the best week-long itineraries in the Leewards because everything is close: three islands, three languages and three moods, with hardly any time spent in transit. Our notes on charter fees explain how a quote is assembled, and our charter fleet shows the yachts available. Speak with the Ahoy Club team about your dates and we will match a yacht and captain to the route.