Catamaran Charter Leeward Islands
The Leeward Islands offer some of the Caribbean's most varied catamaran sailing: consistent trade winds, short inter-island passages, and anchorages ranging from deserted volcanic bays to well-provisioned marina towns.
Catamarans Available in Leeward Islands
Browse our selection of catamarans available for charter in Leeward Islands.
Luxury Crewed Catamaran Lagoon 57
Lagoon 57 · 1995
From
$4k/week
Bareboat Catamaran Bali 4.5 F
Bali 4.5 · 2017
From
$4k/week
Bareboat Catamaran Lagoon 400
Lagoon 400 · 2010
From
$4k/week
Bareboat Catamaran Lagoon 450
Lagoon 450 · 2011
From
$4k/week
Bareboat Catamaran Leopard 39
Leopard 39 · 2012
From
$4k/week
Bareboat Catamaran CORAZON
Bali 4.3 · 2019
From
€5k/week
Bareboat Catamaran CHRYSOMALLOS
Lipari 41 · 2014
From
$5k/week
Bareboat Catamaran Fountaine Pajot Astrea 42
Astrea 42
From
$5k/week
Bareboat Catamaran Lagoon 400 S2
Lagoon 400 S2 · 2013
From
$5k/week
Bareboat Catamaran Lagoon 39 -4 + 2 Cabins
Lagoon 39 · 2013
From
$5k/week
Bareboat Catamaran Lagoon 420
Lagoon 420 · 2008
From
$5k/week
Bareboat Catamaran MOANA
Lagoon 42 · 2019
From
$6k/week
Bareboat Catamaran BELLA LUNA
Bali 4.2 · 2024
From
$6k/week
Bareboat Catamaran BEING NAUTI
Lipari 41 · 2013
From
$7k/week
Bareboat Catamaran Lagoon 440 (2009)
Lagoon 440
From
$7k/week
Bareboat Catamaran Lagoon 450 Luxe
Lagoon 450 Premier · 2016
From
$8k/week
Bareboat Catamaran Lagoon 450
Lagoon 450 · 2012
From
$8k/week
Bareboat Catamaran CATCH THE CAT
Lagoon 450 · 2012
From
$8k/week
Bareboat Catamaran Lagoon 52
Lagoon 52 · 2014
From
$8k/week
Bareboat Catamaran Bali 5.4
Bali 5.4 · 2019
From
$8k/week
Luxury Crewed Catamaran WESTERLUND
Lagoon 46 · 2020
From
€8k/week
Crewed Catamaran DUGONGO II
Lagoon 52 · 2019
From
€10k/week
Luxury Crewed Catamaran ALLADORA
Lipari 41 · 2013
From
$10k/week
Crewed Catamaran HYPNAUTIC
Lagoon 440 · 2007
From
$11k/week
Other Vessel Types in Leeward Islands
Stretching from Anguilla in the north to Guadeloupe in the south, the Leeward Islands reward charterers who want variety without punishing open-water crossings. Passages between islands rarely exceed 30 nautical miles, the north-easterly trades blow at 15-25 knots through most of the year, and the variety of shoreside culture shifts from British-influenced calm to French Creole exuberance within a single day's sail.
A catamaran suits this arc of islands particularly well. The shallow-draught hulls open up anchorages that monohulls must ignore, the wide decks handle the trade-wind chop with composure, and the onboard space means a group of eight or ten can live comfortably for a fortnight without the cabin-fever that close quarters can produce. Whether you charter out of Sint Maarten's Simpson Bay, Antigua's English Harbour, or Guadeloupe's Pointe-à-Pitre, the Leewards offer a genuinely complete sailing circuit.
Why Charter in Catamaran charter in Leeward Islands
The logistical case for the Leewards is straightforward. Sint Maarten and Antigua both have direct transatlantic flights, so a Sunday afternoon arrival and Monday morning departure is realistic rather than aspirational. Charter bases are well-established, provisioning is thorough, and the marinas at IGY Rodney Bay, Simpson Bay, and English Harbour carry the parts and expertise to support any technical query.
Beyond logistics, the sailing itself is legitimate rather than merely scenic. The Anegada Passage, which separates the British Virgin Islands from Anguilla, carries genuine fetch and demands some attention; the channel between St Kitts and Nevis consistently produces 20-knot trades and a lively swell. Sailors who want downwind miles between islands they genuinely want to explore will find the Leewards more satisfying than circuits where the sailing is incidental to the anchorage.
Culturally, no other Caribbean sub-region offers quite this range within a single charter. Gustavia in St Barts operates at a different register from the rum-shop culture of Nevis or the French market in Basse-Terre. A two-week itinerary can move through English, French, and Dutch jurisdictions, eating and drinking accordingly at every stop.
Catamaran charter in Leeward Islands Highlights
The Saintes (Îles des Saintes), Guadeloupe - a French Creole archipelago of volcanic hillside villages, clear water, and mooring fields that reward early arrivals. Terre-de-Haut's single main street and its fish accras are the real draw.
English Harbour and Falmouth Harbour, Antigua - Nelson's Dockyard is genuinely worth exploring beyond the name. The anchorage at Freeman's Bay sits steps from the restored Georgian dockyard buildings, and the chandleries and provisioners mean you can re-stock thoroughly mid-charter.
Gustavia, St Barts - the harbour is small and the moorings fill fast, but Gustavia justifies the effort. Swedish-influenced French Caribbean architecture, restaurants that genuinely rival those in Paris's 6th arrondissement, and a provisioning scene built around the superyacht trade mean standards are consistently high.
Pinney's Beach anchorage, Nevis - anchor off one of the most consistently calm roadsteads in the northern Leewards, with the near-perfect volcanic cone of Nevis Peak providing orientation. The Four Seasons jetty is not the draw here; the beach bars and the quiet are.
The Narrows, St Kitts and Nevis - the two-mile strait between the islands is a short but involving passage with reliable current and consistent trade-wind pressure. Arrive from the Caribbean side and the visual transition from open water to the tight channel is one of the better moments in Leeward sailing.
Grand Case Bay, St Martin - the French side's culinary capital, with a low-key anchorage and a beachfront strip of lolos (roadside barbecue shacks) and proper restaurants sitting side-by-side. Arrive by dinghy from an offshore mooring and eat both ends of the price spectrum the same evening.
Anse de Colombier, St Barts - accessible only by boat or a steep trail, this north-west bay is the most sheltered anchorage on the island and a legitimate escape from Gustavia's social scene. Turtles, clear water, and remarkably little noise.
When to Sail
The Leeward Islands have a defined high season running from December through April, when the north-east trades are most reliable and rainfall is minimal; the summer months are warm, quieter, and still very sailable, though hurricane season officially runs from June through November.
High Season (Jun-Sep)
Counterintuitively, July and August can be excellent sailing months in the Leewards. The trades ease slightly compared to January, sitting around 15-20 knots, making passages more comfortable for less experienced crews. Charter rates are meaningfully lower than the December-April peak, marinas are quieter, and anchorages in Antigua, St Barts, and St Kitts are far less crowded. The trade-off is real: tropical disturbances develop more frequently from August onwards, and charterers should monitor NOAA advisories and ensure their charter agreement includes a clear hurricane protocol. September and October carry the highest statistical risk and are best avoided unless your schedule is highly flexible.
Shoulder Season (May, Oct)
May is arguably the most underrated month in the Leeward Islands calendar. The high-season crowds have thinned, the trades remain reliable at 18-22 knots, and both Antigua Sailing Week (late April into early May) and the surrounding social calendar leave a positive energy in English Harbour. October sits at the statistical peak of hurricane activity and requires careful judgement; some experienced charterers use it specifically for the dramatically reduced rates and near-empty anchorages, but it should not be the default choice for a first Leewards charter.
Choosing the Right Yacht
A catamaran is the natural choice for the Leewards, and not simply because the charter fleet here is built around them. The wide beam and minimal heel make the consistent 15-25 knot trade-wind conditions genuinely comfortable rather than merely manageable for guests who sail occasionally but do not identify as sailors. The shallow draught, typically under 1.2 metres on a 45-50 foot sailing catamaran, opens access to anchorages in the Saintes, around Nevis, and in St Barts that deeper-draught vessels must bypass. The cockpit and deck space matter too: with eight guests aboard, a Lagoon 560, Leopard 50, or Fountaine Pajot Saba 50 provides the equivalent of a well-arranged terrace rather than a crowded stern platform. For those who prefer not to manage sails at all, the Aquila 54 Power Catamaran and comparable models give the same stability and space advantages with point-to-point passage times that allow an ambitious itinerary without early departures. Power cats make particular sense for a shorter charter of seven days, where maximising time in harbour matters more than the sailing itself. The widest beam in the fleet, represented here by the Lagoon Seventy 7, suits larger groups of ten to fourteen guests for whom the yacht is the primary venue and the inter-island sailing is context rather than sport.
Seven Days through the Northern Leewards from Sint Maarten
A suggested week-long charter route
Board at Simpson Bay, Sint Maarten and complete formalities at the lagoon's well-organised check-in. Spend the first afternoon provisioning at the marina's well-stocked chandlers and supermarkets. An evening at Grand Case on the French side requires only a short motor north along the coast; anchor off and dinghy in for dinner at one of the beachfront restaurants.
Depart early on a broad reach south-east to St Barts, a 20-nautical-mile passage that takes around three hours in typical trade conditions. Mooring buoys at Anse de Colombier on the north-west tip are the preferred first stop; collect one before lunch and use the afternoon for snorkelling and swimming before motoring around to Gustavia for the evening.
A full day in Gustavia and the surrounding bays. Provisions top-up at the Marché if needed; use the morning for the market and the afternoon for a swim at Anse du Gouverneur on the south coast, reached by dinghy in settled conditions. Return to Gustavia for dinner ashore.
Sail south-west to St Kitts, approximately 35 nautical miles on a comfortable beam reach. Anchor off Ballast Bay or White House Bay on the south-east peninsula, where the water is clear and the landscape volcanic. An afternoon snorkel and a sundowner on deck before a quieter evening aboard.
Motor through The Narrows and anchor off Pinney's Beach, Nevis, arriving before the day's best light fades. This is a full-day stop: the volcanic backdrop, the calm anchorage, and the beach bars justify the pace. Charlestown's small waterfront repays an evening dinghy trip for rum and local food.
A longer passage day: Nevis to Anguilla, roughly 55 nautical miles on a north-north-west heading. Depending on departure time and conditions in the Anegada Passage approaches, this takes six to eight hours. Road Bay (Sandy Ground) in Anguilla is a calm overnight anchorage with straightforward formalities and a good dinghy-landing beach.
Use the morning to explore Road Bay and Sandy Ground village before a final downwind run back to Sint Maarten, 20 nautical miles south-east. Return to Simpson Bay, complete departure formalities, and use the afternoon for a farewell dinner at one of the marina's restaurants before disembarkation the following morning.
Local Tips
- •Customs and immigration formalities differ at every island and some require advance online pre-clearance. St Barts (via the French Antilles system), Antigua (eSeaClear), and Sint Maarten each have separate processes. Your charter base briefing will cover the current requirements, but build at least an extra hour into any passage that crosses a jurisdictional boundary.
- •Provisioning quality varies significantly across the Leewards. Sint Maarten's Simpson Bay lagoon has the widest selection and most competitive pricing in the region, making it the logical point for a full charter provisioning. St Barts has excellent but premium-priced provisioners near Gustavia's harbour. Nevis and Anguilla have limited supermarket options and are best treated as supplementary stops.
- •The mooring field at the Saintes is managed and fills by mid-morning during high season. If your itinerary includes Terre-de-Haut, plan to arrive before 09:00 or be prepared to anchor in the less sheltered outer areas. The same applies at Anse de Colombier in St Barts, where the National Park buoys are first-come, first-served.
- •French-side customs in St Martin differ from Dutch-side Sint Maarten: no formal check-in is required when moving between EU overseas territories (St Barts and Guadeloupe are both French), but you must clear in properly when crossing to non-EU islands. Carry ship's papers and passports accessible at all times.
- •The Atlantic swell in the Anegada Passage can reach two to three metres even in settled conditions, as it carries fetch from thousands of miles to the east. Crew who are susceptible to motion sickness should take precautions before any passage north of Anguilla or into open-Atlantic-facing anchorages.
- •Gustavia's harbour operates a strict no-anchor policy to protect the seabed. Mooring buoys are available but in short supply; berths alongside the quay are bookable through the port authority and worth reserving in advance during December through April.
Frequently Asked Questions
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