Sailing Yacht Charter Leeward Islands
From Antigua's English Harbour to the volcanic silhouette of Montserrat, the Leeward Islands offer serious blue-water sailing across some of the most reliably wind-filled passages in the Caribbean — best explored under sail.
Sailing Yachts Available in Leeward Islands
Browse our selection of sailing yachts available for charter in Leeward Islands.
Crewed Sailing Yacht THE BLUE PETER
Classic 20m · 1930
From
€3k/week
Bareboat Sailing Yacht Oceanis 48
Oceanis 48 · 2013
From
$3k/week
Bareboat Sailing Yacht Bavaria 40
Bavaria 40 · 2010
From
$3k/week
Bareboat Sailing Yacht Beneteau Oceanis 45
Oceanis 45 · 2013
From
$3k/week
Bareboat Sailing Yacht XERES
Sun Odyssey 509 · 2014
From
€3k/week
Bareboat Sailing Yacht Sun Odyssey 509
Sun Odyssey 509 · 2013
From
€3k/week
Bareboat Sailing Yacht RIOJA
Sun Odyssey 509 · 2014
From
$4k/week
Bareboat Sailing Yacht Sun Odyssey 469
Sun Odyssey 469 · 2013
From
$4k/week
Bareboat Sailing Yacht ISLE DANCE II
Beneteau 50 · 2008
From
$5k/week
Bareboat Sailing Yacht Sun Odyssey 509 Super Premier
Sun Odyssey 509 · 2014
From
$5k/week
Bareboat Sailing Yacht FRENCH MAID
Sun Odyssey 509 · 2012
From
$6k/week
Bareboat Sailing Yacht NO REGRETS
Oceanis 55 · 2013
From
$6k/week
Luxury Crewed Sailing Yacht SALAMANDER
Nauticat 58 · 1987
From
$11k/week
Luxury Crewed Sailing Yacht SAYANG
Sun Odyssey 54 DS · 2005
From
$11k/week
Luxury Crewed Sailing Yacht XIMERA
Hanse 575 · 2014
From
$14k/week
Crewed Sailing Yacht THE ROYAL BLUE
Hylass 70 · 2009
From
$17k/week
Luxury Crewed Sailing Yacht NOHeea
Custom build · 1991
From
€19k/week
Crewed Sailing Yacht BODHISATTVA
Jeanneau 64 · 2018
From
$23k/week
Luxury Crewed Sailing Yacht BODHISATTVA
Jeanneau 64 · 2018
From
$23k/week
Luxury Crewed Sailing Yacht JERSEY GIRL
Oyster 655 · 2008
From
$24k/week
Luxury Crewed Sailing Yacht CAP II
CNB Bordeaux Sloop · 1992
From
$26k/week
Crewed Sailing Yacht VIVID
Jongert 2700M · 2001
From
€28k/week
Crewed Sailing Yacht CIRRUS
Custom Sailing Yacht 68 ft · 2024
From
$30k/week
Crewed Sailing Yacht CHAMPAGNE HIPPY
Oyster 825 · 2014
From
€30k/week
Other Vessel Types in Leeward Islands
The Leeward Islands arc north-west from Guadeloupe through Antigua, Barbuda, St Kitts, Nevis, Montserrat, Anguilla, and St Martin/St Maarten, forming a chain that rewards charterers who want genuine Atlantic sailing rather than gentle motor-sailing between crowded anchorages. The trade winds here blow with purpose, typically 15 to 25 knots from the north-east between December and June, making the inter-island passages fast, predictable, and genuinely satisfying for anyone who has a sail to put up.
The diversity across this relatively compact region is considerable. Antigua hosts one of the Caribbean's finest sailing infrastructures at Falmouth and English Harbour, while the limestone flats of Barbuda offer remote anchorages that feel genuinely undiscovered. St Kitts and Nevis carry a different register — volcanic, steep-to, with sugar-estate architecture and extraordinarily calm western lee anchorages. To the north, Anguilla's shallow turquoise banks and St Martin's cosmopolitan dining scene provide natural bookends to an itinerary that can be as social or as solitary as you choose.
Why Charter in Sailing Yacht charter in Leeward Islands
For sailing yacht charterers specifically, the Leewards present a compelling argument: the passages are real. The channel between Antigua and Barbuda is open ocean. The run from Nevis to St Kitts Narrows demands attention to the acceleration zones generated by the island's volcanic mass. These are not puddle-hops. On a well-crewed 50-plus-foot sailing yacht, they are exhilarating; on a smaller vessel, they require respect and good forecasting. The reward is an arc of islands where you can genuinely feel the Atlantic beneath you, not just a sheltered lagoon.
The sailing infrastructure is among the strongest in the Eastern Caribbean. Antigua Sailing Week in late April draws the world's racing fleet, but the island functions as a provisioning and technical hub year-round. Falmouth Harbour Marina and the adjacent Antigua Yacht Club Marina offer fuel, water, chandlery, and haul-out facilities that can handle vessels up to 100 metres. Further north, Sint Maarten's Simpson Bay Lagoon provides one of the region's largest and best-equipped marina complexes, with duty-free provisioning, world-class repair yards, and direct international air connections.
Beyond logistics, this is a region with genuine cultural texture. Antigua's cricket tradition and carnival in August, the Afro-Caribbean heritage of Nevis, the Creole-French cooking of Guadeloupe's northern dependency at St Martin — these are places with distinct identities, not interchangeable resort islands. Charter here and you are sailing through four centuries of Atlantic trade history, past plantation great houses, colonial fortifications, and fishing communities where the rhythms of daily life have little to do with tourism.
Sailing Yacht charter in Leeward Islands Highlights
English Harbour and Falmouth Harbour, Antigua — Nelson's Dockyard, restored Georgian naval architecture, Shirley Heights Sunday barbecue with views down to the harbour entrance, and the most active sailing scene in the Eastern Caribbean.
Barbuda's western anchorage off Palmetto Point — a genuinely remote overnight stop in shallow, transparent water, with frigate bird colonies at Codrington Lagoon accessible by dinghy. Post-Hurricane Irma infrastructure remains minimal, which keeps the crowds away.
Nevis, Pinney's Beach anchorage — anchor off the dark-sand beach below Hamilton Estate, visit the Bath Hotel ruins, and dine at Nisbet Plantation's terrace overlooking the channel to St Kitts. The passage between the two islands through the narrows is one of the Leewards' more technical short hops.
Gustavia Harbour, St Barthélemy — often considered a Windward stopover but reachable from St Martin in an easy day sail to the north-west. The anchorage is tight and mooring buoys fill fast; arrive by noon. The provisioning at Le Select and the Thursday evening sailing club scene are worth the anchor-watch.
Simpson Bay Lagoon, St Maarten/St Martin — the lagoon entry through the Simpson Bay Bridge (opening hours are published weekly) leads to a marina ecosystem where serious bluewater yachts are provisioned and maintained. The French side's Grand Case village remains the finest concentration of Creole cuisine in the northern Leewards.
The Salt Pond, Anguilla's Road Bay — Anguilla requires a specific clearance stop but rewards with the clearest water in the Leewards and consistently cited beach restaurants at Shoal Bay East. The island rises barely a few metres above sea level, making it easy to spot from offshore and harder to make out until you are nearly upon it.
Redonda — the uninhabited volcanic plug between Montserrat and Nevis, rising 300 metres from the sea with no safe landing in anything but flat calm. Passing it on a broad reach in 20 knots of trade wind, with boobies wheeling overhead, is one of those unrepeatable Caribbean sailing moments that no marina can replicate.
When to Sail
The Leewards sail well from December through to June, when the north-east trades are steady and the risk of tropical weather is minimal. The summer months bring lighter, more variable winds and an elevated hurricane risk from August onwards, though experienced charterers still find excellent conditions in July.
High Season (Jun-Sep)
This label is somewhat misleading in the Leewards — June and early July can offer superb, less crowded sailing as the trades begin to ease slightly and rainfall remains low. By August, the Inter-Tropical Convergence Zone pushes north and hurricane season commands serious attention; most experienced charterers and their skippers track forecasts closely and many operators move vessels south of 12°N. September is statistically the peak of hurricane activity and charter bookings are at their lowest. Rates are lower, marinas quieter, but the prudent charterer needs a clear weather-watching protocol and flexible cancellation terms in place.
Shoulder Season (May, Oct)
May is arguably one of the finest months to sail the Leewards. The trades are still reliable, air temperatures are warming rather than oppressive, and the winter charter crowd has thinned. Anchorages that were rafted three-deep in February are accessible with room to breathe. October sits at the tail end of hurricane season and carries risk; however, the second half of October and early November — the unofficial 'shoulder' period before the charter season officially reopens — can deliver glassy calms and dramatic skies. Many professional crews use this window for repositioning passages.
Choosing the Right Yacht
The Leewards are designed for sailing yachts. The consistent north-easterly trades, the upwind work required to beat back from St Martin to Antigua, and the open-ocean passages between islands all reward boats with genuine windward performance and range. A well-found monohull in the 45 to 70-foot bracket — think CNB Bordeaux Sloop or a Jeanneau 64 — handles the inter-island chop comfortably, points high enough to make the windward passages manageable, and fits into anchorages that a wide catamaran cannot access. For larger groups or those who prioritise deck space over sailing purity, the larger sailing yachts in the 80-plus-foot bracket — custom builds and the Alloy Yachts and Holland Jachtbouw vessels represented in our fleet — offer the range and comfort to run extended itineraries with professional crew without compromising on genuine offshore sailing capability.
Seven Days Through the Northern Leewards — Antigua to St Martin
A suggested week-long charter route
Join your vessel in Falmouth Harbour, Antigua. Afternoon briefing with the captain, provisioning check, and a walk through Nelson's Dockyard before dinner at the Copper and Lumber Store. Overnight in the marina.
Depart Falmouth on the morning trade. Sail north to Barbuda — approximately 27 nautical miles from Antigua's north coast, a straightforward reach in settled trades. Anchor off Palmetto Point by early afternoon. Dinghy to Codrington Lagoon before sunset.
A full day at Barbuda. Early morning snorkel off the reef fringing the western shore, then north by dinghy to the frigate bird sanctuary. The flat sandy profile of the island creates an unusual microclimate; afternoons can be gusty from the north-east, so set a second anchor if holding is soft.
West and then north. Leave Barbuda by 0700 to catch the best of the morning breeze for the 60-nautical-mile run to St Kitts. The passage opens onto the Atlantic briefly before you gain the lee of the island chain. Anchor at White House Bay on St Kitts' south coast — calm, clear, with a wreck accessible to snorkellers just off the beach.
Motor or sail the short narrows to Nevis. Anchor at Pinney's Beach by mid-morning. Afternoon ashore — Mount Nevis trail for the energetic, Nisbet Plantation for those who prefer a rum punch in the shade of a 300-year-old great house. Overnight on the hook.
The day's sail north to Anguilla and Road Bay covers approximately 55 nautical miles and takes you back into open water between St Kitts and St Maarten. Clear in at Road Bay, then dinghy ashore to Sandy Ground for late lunch. The passage can be bumpy on the beam if the trades have built overnight; a 0600 departure typically catches the calmest conditions.
Final leg to Simpson Bay, St Maarten — a short 15-nautical-mile sail south-east across the Anguilla Channel. Time the Simpson Bay Bridge opening for your lagoon entry. Handover formalities at the marina; international departures from Princess Juliana Airport are walkable or a short taxi ride.
Local Tips
- •Customs and immigration vary by island and require separate clearance. Antigua, St Kitts and Nevis, and Anguilla are each independent or separately administered territories; St Martin/St Maarten has French and Dutch sides with their own protocols. Budget time for these formalities and ensure your captain carries all relevant ship's papers, crew lists, and advance arrival notifications where required.
- •Provisioning in Antigua is the most reliable in the chain. Budget Provisioning in Falmouth and the Epicurean supermarket at Woods Centre both deliver to the dock. If you are running north to Anguilla or beyond, take on full provisions in English Harbour rather than relying on the limited options in smaller islands.
- •The Antigua to Barbuda channel is open Atlantic fetch. Seas of two to three metres are not unusual, particularly in February and March when the winter swell patterns are at their strongest. Confirm that all guests are prepared for offshore conditions before departing; the passage takes three to four hours in average conditions.
- •Anguilla imposes a departure tax that must be settled in cash at the port authority. The island has no significant marina — anchoring is the norm and holding in Road Bay is adequate but exposed to northerly swell. Brief your guests accordingly before arrival.
- •Creole cuisine on the French side of St Martin rewards deliberate exploration. Grand Case's restaurant row on Boulevard de Grand Case is not a tourist trap — establishments like L'Estaminet and the local lolos (open-air barbecue stalls) offer genuinely good cooking. Book ahead for dinner at the better restaurants during high season.
- •Squalls build quickly on the Leeward-facing slopes of the volcanic islands, particularly Montserrat, St Kitts, and Nevis. A radar watch after 1400 is standard practice. The squalls typically pass in 15 to 25 minutes but can push 35 knots at their core; reef early rather than reactively.
Frequently Asked Questions
Do I need a sailing licence to charter a yacht in the Leeward Islands+
What is the best base for a Leeward Islands sailing charter+
How far in advance should I book a sailing charter in the Leewards+
Is the Leeward Islands route suitable for children+
What currency and payment methods are used across the Leeward Islands+
Can I sail to St Barthélemy from the Leeward Islands itinerary+
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