Windward Islands Yacht Charter: Three Borders, One Week

They are called Windward because they sit on the windward side of the Lesser Antilles, taking the Atlantic trades before the Leewards do. That is also why they sail well: the wind is reliable and the run from St Lucia south to Grenada is mostly downwind.

The chain is wetter, greener and much less built up than the Leewards. Martinique is French, with a marina at Le Marin holding 830 berths and 100 buoys — the largest nautical base in the West Indies. St Lucia is volcanic and vertical: the Pitons rise 770m and 743m straight out of the sea and have been a UNESCO World Heritage Site since 2004. St Vincent’s La Soufrière stands 1,220m and last erupted in 2021.

South of St Vincent the islands break up into the Grenadines — Bequia, Mustique, Canouan, Mayreau, the Tobago Cays, Union Island, then Carriacou and Grenada. This is the part people charter for. The Tobago Cays are five uninhabited islands inside a horseshoe reef, and there is nothing else quite like them in the Caribbean.

What is each Windward island actually like?

DominicaMartiniqueSt LuciaSt VincentBequiaMustiqueTobago CaysUnion IslandCarriacouGrenada

ADD-ON · TEN DAYS

Dominica

Portsmouth & Roseau · Two ports of entry · US$12 park week pass

The Nature Island, north of Martinique. Two ports of entry, Portsmouth and Roseau. National park sites are charged separately — US$5.00 for one site, US$12.00 for a week pass covering all of them. Worth ten days rather than seven.

FRENCH · NORTH END

Martinique

Le Marin · 830 berths · TVA 8.5%

French in the way that involves patisseries. Marina du Marin holds 830 berths, 100 buoys and more than 80 marine trades on site, the largest nautical base in the West Indies. Clearance is computerised and quick. Airport: Aimé Césaire (FDF).

THE STARTING LINE

St Lucia

Rodney Bay · 253 berths · Pitons 770m and 743m

Where most weeks begin. Rodney Bay Marina has 253 berths, 32 of them for megayachts, and takes yachts to 285ft. Soufrière and the Pitons — a UNESCO World Heritage Site since 2004 — are a morning’s sail south. Airport: Hewanorra (UVF).

THE VOLCANO

St Vincent

La Soufrière 1,220m · Last erupted 2021 · SVD

The volcano island. La Soufrière stands 1,220m and erupted as recently as 2021. Most charters pass through on the way south to the Grenadines rather than linger. Airport: Argyle (SVD).

FIRST GRENADINES STOP

Bequia

Port Elizabeth · Port of entry · ~46nm from St Lucia

A working boatbuilding island with a real harbour at Port Elizabeth, and a St Vincent and the Grenadines port of entry. The first proper Grenadines night after the week’s one long passage.

PRIVATE

Mustique

~8nm from Bequia · Access arranged in advance

Tightly controlled and about 8nm from Bequia. Anchoring and shore access are regulated by the Mustique Company, so your broker confirms the arrangements before you sail.

WHY PEOPLE COME

Tobago Cays

Five uninhabited islands · Horseshoe Reef · Marine park

Five uninhabited islands inside Horseshoe Reef, all of it a marine park. Park entry and mooring are charged by the park authority. Too small to register on 1km land data, so they are marked here rather than drawn. Nothing else in the Caribbean is quite like them.

SOUTHERN CLEARANCE

Union Island

Clifton · ~4nm from the Cays

Clifton is the southern clearance point for St Vincent and the Grenadines, roughly 4nm from the Tobago Cays, and where most weeks clear out before crossing to Grenada.

GRENADIAN, QUIET

Carriacou

Tyrrel Bay · Northern clearance for Grenada

Grenadian, quiet, and the northern clearance point for Grenada at Tyrrel Bay — one of the emptiest good anchorages in the chain.

THE FINISH

Grenada

St George’s & Port Louis · VAT 15% · GND

The Spice Island, and the usual end of the week. St George’s and Port Louis, then home from Maurice Bishop International (GND). Grenada charges VAT at 15%, with a reduced 10% rate on hotel accommodation and dive operations.

Select an island name to see what it offers. Coastlines are real, drawn from 1km public-domain land data on an equirectangular projection — but this is a schematic and must not be used for navigation. The Tobago Cays are too small to register at that resolution, so they are marked rather than drawn. Unlabelled grey landmasses are Canouan, Mayreau, Petit St Vincent and the smaller Grenadines, which sit in the chain but are not covered here.

How much does a Windward Islands yacht charter cost?

A crewed catamaran in the Windward Islands runs roughly $15,000–$45,000 a week and is usually all-inclusive. Sailing yachts of 60–100ft run $40,000–$150,000 and motor yachts of 50–130ft run $20,000–$250,000+, both plus an Advance Provisioning Allowance of 25–35% of the base fee. Superyachts above 150ft start around $300,000.

These are the bands we quote from across our fleet — the same figures published on our full charter cost breakdown, reviewed August 2026. Where a yacht sits inside its range comes down to age, refit history, crew size and how contested the week is. Christmas in the Grenadines is not the same number as the same yacht in early December.

Crewed catamaran45–62 ftSailing yacht60–100 ftMotor yacht50–130 ftSuperyacht150 ft+

$15,000–$45,000per week

Length

45–62 ft

Pricing model

Often all-inclusive — no APA

Suits

Families, a first Caribbean charter, and the shallow Tobago Cays anchorages

See crewed catamarans in the fleet

$40,000–$150,000per week

Length

60–100 ft

Pricing model

Plus expenses — APA 25–35%

Suits

The downwind run from St Lucia to Grenada, which is what this chain is built for

See sailing yachts in the fleet

$20,000–$250,000+per week

Length

50–130 ft

Pricing model

Plus expenses — APA 25–35%

Suits

Reaching Dominica or Martinique without losing two days, and multi-island weeks

See motor yachts in the fleet

$300,000–$1,000,000+per week

Length

150 ft+

Pricing model

Plus expenses — APA 25–35%

Suits

Rodney Bay berths to 285ft, Mustique, large parties, maximum privacy

See superyachts in the fleet

What sits on top of the base fee:

• APA — 25–35% of the base fee on plus-expenses charters, paid before you board. This is your money, not a fee. The captain draws from it for fuel, provisioning, dockage, permits and local duties, accounts for every line, and returns the balance. Most crewed catamarans are all-inclusive instead and carry no APA.
• Crew gratuity — 10–20%, discretionary, paid at the end of the charter.
• Local duties — three borders in a week, plus marine park fees in the Tobago Cays and at Soufrière. Itemised below.

Compare the yacht types in detail: crewed catamaran charters, crewed sailing yachts and motor yacht charters, or browse the fleet. New to this? Start with how chartering works, start to finish.

When is the best time to charter in the Windward Islands?

December through April is high season, peaking over Christmas and New Year. Average highs sit at 83–85°F from January to April. Météo-France records trade winds of 30–50 km/h — roughly 16–27 knots — through the February-to-April Carême. Atlantic hurricane season runs 1 June to 30 November, peaking on 10 September.

Most crewed yachts leave the region for the summer, so the fleet thins from June. The Windwards sit further south than the Leewards, which shortens the exposure but does not remove it — the season still ends on the same date. If a summer week is on the table, read our trip cancellation insurance page first.

How many islands fit into a one-week charter?

Realistically five to seven anchorages. Rodney Bay to Soufrière is a morning. St Lucia down to Bequia is the week’s one long passage, roughly 46 nautical miles across open water. Most weeks run one way — St Lucia to Grenada — so the yacht sails downwind all week and you fly home from the other end.

Where does a Windward Islands charter start?

Most charters begin in St Lucia and end in Grenada. Hewanorra International (UVF) at Vieux Fort is the long-haul airport, and Rodney Bay Marina is the boarding point — 253 berths including 32 for megayachts, taking yachts to 285ft with 13ft of draft. Grenada’s Maurice Bishop International (GND) is the usual flight home.

• Rodney Bay Marina, St Lucia. 253 berths, 32 megayacht berths, max LOA 285ft (86.8m), max beam 60ft, max draft 13ft, and a 75-tonne travelift. A port of entry. (IGY Marinas)
• Marina du Marin, Martinique. 830 berths, 100 buoys and more than 80 marine trades on site — the largest nautical base in the West Indies. Clearance is computerised and quick. (Comité Martiniquais du Tourisme)
• Port Elizabeth, Bequia. A St Vincent and the Grenadines port of entry, and the natural mid-week clearance point.
• Clifton, Union Island. The southern clearance point for St Vincent and the Grenadines, closest to the Tobago Cays.
• Tyrrel Bay, Carriacou and Port Louis, St George’s. Grenada’s two most-used clearance points for charter yachts.

What paperwork and taxes apply in the Windward Islands?

A one-week Windward charter crosses three borders — St Lucia, St Vincent and the Grenadines, and Grenada — and you clear out of each before clearing into the next. Add Martinique or Dominica and it becomes four or five. Your captain handles all of it and the cost comes out of the APA.

We are charter brokers, not tax advisers. Your broker confirms in writing which duties apply to your yacht, flag and itinerary before you sign anything. New to the process? See how chartering works, start to finish.

What is on in the Windward Islands this season?

The Windwards have a shorter events calendar than the Leewards, but the dates that exist move rates. If your week overlaps one of these, book early.

Who plans your charter?

Two brokers, both named, both reachable directly. You get one of us from the first call to the day you step aboard — not a queue, and not a form that disappears into a shared inbox.

Windward Islands or Leeward Islands — which should you charter?

Choose the Leewards for range, borders and the St Barths scene. Choose the Windwards for sailing and reefs: one downwind run from St Lucia to Grenada, short hops through the Grenadines, and the Tobago Cays, which have no equivalent further north. The trade-off is fewer restaurants and one long open-water passage.

Planning the other side of the comparison? See our Leeward Islands charter guide.

Windward Islands yacht charter FAQs

Keep planning

Chartering elsewhere in the region? Start with the wider Caribbean charter guide, or compare the Leeward Islands further north. Thinking about a summer week? Read trip cancellation insurance before you book inside hurricane season, which runs 1 June to 30 November. The Tobago Cays reef makes this chain strong for diving and snorkelling charters, and you can always browse the fleet first.