St Barths & the Leeward Islands

Three islands, three jobs

Everything in the northern Leewards is a day sail. St Barths to St Martin is 15 nautical miles, to Anguilla about 30, to St Kitts about 40. Antigua is 85 miles south and is the one real passage, usually done overnight or as a long reach in the trades. Barbuda lies 30 miles north of Antigua, Guadeloupe 40 miles south.

A week is St Barths and its neighbours. Two nights in Gustavia, a day at Anse de Gouverneur or Saline, a run to Anguilla for Sandy Island and the beach restaurants, a night off Ile Fourchue, and back. Two weeks adds the passage south to Antigua and Barbuda, with St Kitts and Nevis on the way and Guadeloupe and Les Saintes beyond. Owners who want to keep the boat in one place all winter usually base at Sint Maarten or Antigua and use St Barths in bursts.

The anchorages, and the size trap

St Barths has two of the best anchorages in the Caribbean and a large yacht cannot use either of them. The nature reserve prohibits vessels over 25 metres from entering it altogether, which closes Colombier and Ile Fourchue to anything of superyacht size, and inside those two bays mooring is on buoys only, capped at four consecutive days. The workable anchorages for a big boat are the outer harbour at Gustavia, Anse de Gouverneur and Grande Saline on the south coast, and Baie de Saint-Jean. All three of the south coast bays are open to swell.

Elsewhere the choice is wide. Anguilla's cays are the prettiest water in the group, with Sandy Island, Prickly Pear and the Rendezvous Bay stretch, and the island charges its own cruising and marine park fees. Around Antigua there are dozens of bays, from Deep Bay and Jolly Harbour on the west to Green Island and Nonsuch Bay on the east, plus the shelter inside English and Falmouth.

The two best anchorages on St Barths are closed to any yacht over 25 metres, which is not what the photographs suggest.

Gustavia, the bridge and Falmouth

Gustavia is smaller than its reputation. It runs about 60 dockside slips with a maximum of roughly 60 metres and around 4.5 metres of draft, and yachts berth stern-to on their own anchor. Everything larger anchors in the outer harbour and tenders in. Entry requires authorisation from the port captain's office, which is called on VHF 12 before manoeuvring, and there is a 5 knot limit inside the port. Over Christmas and New Year the outer anchorage holds a hundred yachts and more.

Sint Maarten is where the size question bites hardest. The Simpson Bay Lagoon holds the region's marinas and refit capacity, and the Dutch-side bridge into it has a clear width of 17 metres, so a modern 50 metre yacht with a wide beam physically cannot get in. Bridge openings run to a published timetable, outbound at 08:30, 10:30 and 16:00 and inbound at 09:30, 11:30, 14:00 and 17:00, and they change, so this is checked and not assumed. Antigua has none of that difficulty, and Falmouth Harbour Marina takes yachts to about 163 metres with up to 6 metres of draft, and Nelson's Dockyard in English Harbour takes about 55 metres stern-to against a Georgian quay.

Trade winds, swell and the months

The season is framed by the Atlantic hurricane season, which officially runs 1 June to 30 November, and most insurance policies require the yacht to be out of the box or in an approved location for the middle of it. December through April is warm, dry and steady, with daytime temperatures in the high twenties and water that needs no wetsuit. The trades blow northeast at 15 to 25 knots for weeks at a time, which is why the sailing here is the best in the world and why the exposed anchorages are rolly.

The variable that catches people out is the winter northerly swell. Distant North Atlantic storms send long-period swell down into the Leewards from December to March, and it makes north-facing bays and harbours uncomfortable or untenable for two or three days with no local wind to explain it. Christmas winds, a period of reinforced trades in late December and January, are the other seasonal feature. February and March are usually the steadiest weeks.

New Year, the Bucket and Sailing Week

The Caribbean season has one immovable week and it is the last of the year. St Barths at New Year is the densest gathering of large yachts anywhere outside the Monaco show, with the outer harbour full, the town at capacity and berth and mooring arrangements made many months in advance. Everything about that week costs more and books earlier than an owner expects.

The racing calendar then takes over. The St Barths Bucket runs 12 to 15 March 2026 and turns Gustavia into a gathering of the largest sailing yachts afloat. Les Voiles de Saint-Barth follows in April. Antigua Sailing Week runs 22 to 26 April 2026 out of Falmouth and English Harbours, preceded by the Antigua Classic Yacht Regatta. In December the Antigua Charter Yacht Show fills Falmouth with the charter fleet and the brokers, which matters to any owner running the boat commercially.

Why guests fly into Sint Maarten

St Barths has an airport and it will not help. Gustaf III at Saint-Jean has a very short runway with a steep approach over a hillside, and it takes only small turboprops and light aircraft, so private jets cannot land there. Guests fly into Princess Juliana on Sint Maarten, which has long-haul service from Europe and North America and full business aviation handling, and then transfer by light aircraft, helicopter or the twenty minute ferry. Antigua's V C Bird airport takes wide-body long haul direct from London and North America and is the easiest arrival in the eastern Caribbean.

That transfer is the single most underestimated part of a St Barths week. The connection adds an hour or two at each end and it is weather-dependent, the last light aircraft rotations are early in the evening, and at Christmas the whole system is saturated. Antigua avoids all of it, which is one reason a lot of large boats now winter there instead.

Dinner on St Barths, beaches on Anguilla

St Barths is French and expensive and it does one thing extremely well, which is dinner. Bonito and Le Ti Saint Barth in Gustavia, Shellona on Shell Beach, Nikki Beach at Saint-Jean and the restaurant at Eden Rock are the fixtures, and the beach at Gouverneur has nothing on it at all. The shopping is duty free and the island has no VAT, which is a real difference in price on watches, jewellery and wine. The nightlife is a handful of venues and a lot of yacht crews.

The neighbours are not runners-up. Anguilla has the best beach restaurants in the Caribbean, Blanchards and Straw Hat among them, and no crowds. Antigua's Nelson's Dockyard is a restored Georgian naval yard and a UNESCO World Heritage site, with the Sunday evening barbecue at Shirley Heights above it that everybody ends up at once. Sint Maarten has the chandlers and the supermarket and very little else.

Clearance, fees and support

Clearance is the recurring chore, because this is a chain of small islands under four or five different flags and a yacht clears in and out of each one. St Barths and the French side of St Martin are French, the Dutch side of Sint Maarten runs its own arrangements, and Anguilla, Antigua and St Kitts are independent or British and each charge cruising permits and fees. St Barths has been an EU overseas country and territory since 1 January 2012, which puts it outside the EU customs and VAT area while it continues to use the euro. Agents handle all of this and are worth having.

Sint Maarten's lagoon is the technical centre of the eastern Caribbean, with the yards, the chandlers, the fuel and the freight, and Antigua is the second base with good marine trades around Falmouth. Between them they cover most of what a large yacht needs in a season. Everywhere else is thin, and a serious failure in Anguilla or Barbuda means a delivery to Sint Maarten.

The honest downside

The reserve rule at St Barths is the thing owners find hardest to accept, because the two best bays on the island are closed to their yacht and the boat spends the week in an open roadstead off Gustavia or on the exposed south coast. In fresh trades and a northerly swell that is a rolly week, and stabilisers work hard. Gustavia's berths are few, the New Year premium is severe, and the island's shore prices are among the highest in the world.

The wider point is that this is a hurricane coast with a memory. Irma in September 2017 devastated Sint Maarten, St Martin and parts of Anguilla and Barbuda, and rebuilding has taken years, which shows in patchy infrastructure and in insurance terms for the summer months. The season is also short, roughly December to April, so a yacht kept here works five months and then repositions or lays up. Owners who want a Caribbean base without that clock usually end up looking further south.

The one real saving, and everything that is not published

St Barths is where the tax answer is the simplest on this list and the price answer is the hardest. The island has been an EU overseas country and territory since 1 January 2012, which puts it outside the EU customs and VAT area while it continues to use the euro. There is no VAT on anything bought ashore, none on fuel and none on services, which is a measurable difference against the French mainland where the same purchase carries 20 per cent, and it is the reason watches, jewellery, wine and provisioning are genuinely cheaper here rather than merely presented that way. The same status means the EU's 18 month temporary admission clock does not run in these waters at all, because the yacht is not inside the customs union, so a Caribbean winter is time that does not count against a Mediterranean summer.

Against that, almost nothing is published. Port de Gustavia posts no berthing or anchoring tariff and none was obtainable in July 2026, so no figure is offered here rather than a guess. The reserve moorings at Colombier and Ile Fourchue are reported to be free and are limited in number, capped at four consecutive days, and closed in any case to vessels over 25 m, so the mother ship is not using them and the question does not arise for her. What can be budgeted with confidence is the clearance chain rather than the berth. This is a chain of small islands under four or five flags and a yacht clears in and out of each of them, with Antigua's Port Authority collecting entrance, rubbish, anchorage or dockage and cruising permit fees at the counter in US or East Caribbean dollars. The agent's fee is the predictable line in a Leewards budget and the berth is not.

Whether a foreign flag may charter in the Leewards

There is no single answer here because there is no single jurisdiction, and that is the honest shape of the problem rather than an evasion of it. St Barths sits outside the EU customs and VAT area, so a charter here attracts no French VAT and the EU maritime cabotage regulation does not apply as it does in metropolitan France. Since 1 September 2024 every vessel, private or commercial and whatever her flag or home port, must check in and out on entering or leaving the waters of Martinique, Guadeloupe, Saint-Martin or Saint-Barthelemy, which formalised what had been a variable practice. Beyond the French islands the position changes with the flag ashore. Antigua and Barbuda requires every vessel in its waters to carry a valid cruising permit, issued by the Port Authority or the National Parks for up to a maximum of six consecutive months, and a foreign-flagged vessel operating there is treated as having self-declared compliance with the local small craft regulations as a condition of holding it.

What could not be sourced in July 2026 is a published charter-licence regime for St Barths itself, and the absence of a document should not be read as an absence of rules. The regional pattern is consistent: most Caribbean islands apply no dedicated charter tax or VAT, but they do charge cruising permits, marine park fees, clearance charges and local levies, so the cost of chartering across the Leewards is a stack of small permits assembled island by island rather than one headline rate. The practical consequence is that a week combining St Barths, Anguilla and St Kitts crosses three fee regimes and three clearances, and it is the agent's schedule rather than any tax rate that decides whether the itinerary works. Technical capability is concentrated in the Simpson Bay lagoon at Sint Maarten and around Falmouth in Antigua, so a yacht too beamy for the lagoon's 17 m bridge clearance sits outside the region's main yard cluster before her season begins, and Antigua becomes the answer by default.

Who it is for: An owner who wants the fashionable Caribbean winter and will base the boat at Sint Maarten or Antigua, using Gustavia for the nights that matter.