Leeward Islands yacht charter
Small islands under different flags, from polished St Barths to sandy Anguilla and Antigua's harbour, mostly short hops apart. The season is December to April; March and April are often the best balance. It suits couples and celebrations most.
The Leeward Islands are the northern arc of the Lesser Antilles, a chain of small islands that each belong to a different country or flag. St Barths is French and polished; St Martin is half French, half Dutch; Anguilla is British, low and sandy; Antigua has a harbour that has sheltered ships since the eighteenth century. A week here is short hops between islands that feel quite unlike each other, with the trade wind behind or across you most of the time.
Why go, and whom it suits
Families
Anguilla's long sand beaches and shallow water, and Antigua's sheltered bays on the east side, such as Green Island, are the easiest days with children. The passages between St Martin, Anguilla and St Barths are short.
Couples and honeymoons
St Barths is the obvious one: Colombier's bay, which you reach only by sea or on foot, and dinners in Gustavia. Anguilla's quiet south coast is gentler on the budget ashore.
Friends and celebrations
Christmas and New Year in St Barths are the most sought-after weeks in the Caribbean, with Gustavia harbour full and fireworks over it. Antigua's English Harbour and St Martin's Grand Case restaurants are livelier the rest of the season.
Less suited to anyone who wants calm water every day. Between the islands you are in open sea, and the trade wind makes some crossings lively. Inside a group, such as St Martin, Anguilla and St Barths, the hops are short.
The areas
The Leewards are one of the island groups on our Caribbean, Bahamas and Atlantic page.
St Barths and St Martin
(page to follow). Gustavia, Colombier, Shell Beach and Gouverneur; on St Martin, Marigot, Grand Case and Simpson Bay's lagoon. Princess Juliana airport on the Dutch side is the main gateway.
Anguilla
(page to follow). Low coral island with some of the best beaches in the region: Shoal Bay, Meads Bay, Rendezvous Bay, and the cays of Sandy Island and Prickly Pear.
Antigua and Barbuda
(page to follow). English Harbour and Nelson's Dockyard, a UNESCO World Heritage Site since 2016, Falmouth Harbour, Green Island, and, a longer sail north, Barbuda's pink-sand beaches and its Frigate Bird Sanctuary.
St Kitts and Nevis
(page to follow). Christophe Harbour's marina on St Kitts, Brimstone Hill fortress, a UNESCO World Heritage Site, and Nevis's Pinney's Beach under its volcano.
When to go
Christmas and New Year are the peak, and priced as such; the weeks around them fill earliest. March and April are often the best balance: steady wind, dry weather, fewer people.
The trade wind blows from the east to north-east most of the winter.
The Antigua Charter Yacht Show is in early December (4–9 Dec in 2026), and Antigua Sailing Week at the end of April (21–25 Apr 2027). Harbours are busy and prices higher those weeks.
The hurricane season runs officially from 1 Jun to 30 Nov, with most activity from mid-August to mid-October. Few yachts are here then; most go north or to the Mediterranean.
What it costs
The charter fee is each yacht's own weekly rate. Her page shows it "from", which is her lowest season; Christmas and New Year usually need at least 7 nights and cost more. Shorter than a week is possible on many yachts, priced per day from the weekly rate.
- Taxes and fees differ by island and by the yacht's flag. The French islands, the Dutch side of St Martin, Anguilla, Antigua and St Kitts each have their own rules on charter taxes and fees. Your written quote lists the fee, the VAT rate, the APA, any delivery fee and local taxes.
- APA, the Advance Provisioning Allowance, is paid with the balance: money held by the captain for fuel, food, drinks, berths, clearance fees and similar costs, spent on your instructions and accounted for at the end, with anything unspent returned. Budget up to 40% of the charter fee; long or remote passages can need more.
- Currencies. Each yacht's rate is in its own currency, often US dollars outside Europe. Anguilla, Antigua and Barbuda and St Kitts and Nevis use the Eastern Caribbean dollar. St Barths and French St Martin use the euro.
Our guide sets out what a crewed charter costs, line by line.
The weekly rate on each yacht’s page. "From" is her lowest season.
An advance for fuel, food, drinks and berths, spent on your instructions and settled at the end.
Set by the country the charter starts in, added to the fee.
St Martin, Anguilla and St Barths
Three islands, three flags, and no passage longer than a couple of hours. The yacht and the wind decide the real order.
Board in Simpson Bay or Marigot, close to the airport. Dinner in Grand Case.
A short sail north to another territory, so the crew handles the entry formalities. Swim off Sandy Island and stay for the evening.
Prickly Pear Cays for snorkelling, then round to the south coast and Rendezvous Bay.
A short crossing to St Barths. A night off Colombier; the walk over the hill to Flamands is worth it.
The harbour town: shops, lunch ashore, the evening on the quay.
Two beaches on the south side, both without buildings. A quiet night at anchor.
A morning crossing and disembarkation.
The yachts that cruise here
Most of the yachts we show in the Leeward Islands are motor yachts over 40 metres, with a few catamarans.
Most of them spend the summer in the Mediterranean or in New England and come down for the winter. The yachts on this site are a selection, not the limit of what we arrange: ask about any yacht, of any size.
Practical questions
Rene GaspersicYour broker
Where do charters start?
Most start in St Martin (Simpson Bay or Marigot), St Barths or Antigua. The airport decides as much as the route.
How do we get there?
Fly to St Martin's Princess Juliana airport or to Antigua's airport; both take international flights. St Barths has a short airstrip for small planes, a short hop from St Martin, or a ferry.
Do we clear customs between islands?
Usually yes: each island or country has its own formalities, and the crew handles them with your passports.
Is the sea rough between islands?
The crossings are open sea, with the trade wind. Within St Martin, Anguilla and St Barths they are short; Antigua to St Barths is a long day. The captain picks the hour and the direction.
Can we spend New Year in St Barths?
Yes, if you plan early: it is the busiest week of the Caribbean season, berths in Gustavia are limited and very expensive, and many yachts anchor off. Christmas and New Year usually need at least 7 nights and cost more.
Is it good for children?
Yes, particularly Anguilla and Antigua's sheltered bays. Tell us the ages; it changes which yacht and which route we propose.
Can we combine the Leewards with the Virgin Islands?
Some yachts move between them; the crossing from St Martin to the BVI is a long open-water passage. See the Virgin Islands.
Which currency do we bring?
The euro in St Barths and French St Martin, and the Eastern Caribbean dollar in Anguilla, Antigua and Barbuda and St Kitts and Nevis.
What about the hurricane season?
Charters here run from December to April or May. In summer most yachts are elsewhere, and we will suggest the Mediterranean or New England.
Are the French islands in the EU?
French St Martin is part of the EU and of its customs territory, but outside the EU's VAT area. St Barths is not part of the EU: it is an overseas territory associated with it. It matters for some formalities, not for your week.
Leeward Islands | Windward Islands | |
|---|---|---|
Feel | Polished, beaches, restaurants | Greener, wilder, more remote |
Best known for | St Barths, Anguilla's sand, Antigua's harbour | The Grenadines, the Pitons, the Tobago Cays |
Passages | Short inside a group, open between groups | Short through the Grenadines |
Talk to a broker
Tell us roughly when, how many of you there are, and what the week is for: a family winter break, a honeymoon, New Year with friends. Dates and budget can stay loose. We come back with a short list of yachts that fit, say plainly what each one is like, and stay your contact from the first email to the last day on board.
Rene Gaspersic
charter broker
Email info@soretoyachting.com · Phone +44 7342 933198 · WhatsApp +44 7342 933198
Plan
Leeward Islands.
Two short steps. Dates and budget can stay loose. We reply personally, by email, phone or WhatsApp.