Catamaran Charter Windward Islands
From St Lucia's Pitons to the whaling heritage of Bequia, the Windward Islands reward sailors who want real Caribbean sailing rather than flat-water motor cruising. Trade winds run reliably from the north-east, island cultures diverge sharply from one anchorage to the next, and the distances are forgiving enough to leave afternoons unhurried.
Catamarans Available in Windward Islands
Browse our selection of catamarans available for charter in Windward Islands.
Bareboat Catamaran Lipari 41
Lipari 41 · 2010
From
€3k/week
Bareboat Catamaran Lagoon 380
Lagoon 380 · 2013
From
$3k/week
Bareboat Catamaran Fountaine Pajot Orana 44
Fountaine Pajot Orana 44 · 2010
From
€3k/week
Bareboat Catamaran Fountaine Pajot Orana 44
Fountaine Pajot Orana 44 · 2012
From
€3k/week
Bareboat Catamaran Bali 4.0
Bali 4.0 · 2017
From
€3k/week
Bareboat Catamaran Leopard 4700
Lagoon 4700 · 2001
From
$3k/week
Bareboat Catamaran Catana 50 OC
Catana 50 OC · 2012
From
$4k/week
Bareboat Catamaran RAYVES
Lagoon 400 S2 · 2014
From
€4k/week
Bareboat Catamaran Lavezzi 40
Lavezzi 40
From
€4k/week
Bareboat Catamaran MANUTEA
Lagoon 440 · 2010
From
€4k/week
Bareboat Catamaran Lavezzi 40
Lavezzi 40 · 2010
From
$4k/week
Bareboat Catamaran CALLISTO
Lagoon 450 · 2014
From
€4k/week
Bareboat Catamaran Lagoon 430
Lagoon 430 · 2007
From
$4k/week
Bareboat Catamaran Leopard 46
Leopard 46 · 2010
From
$5k/week
Bareboat Catamaran Catana 47 Custom
Catana 47 · 2010
From
$5k/week
Bareboat Catamaran Fountaine Pajot Helia 44
Fountaine Pajot Helia 44 · 2013
From
€5k/week
Bareboat Catamaran Lagoon 450 F Luxe
Lagoon 450 F Luxe · 2017
From
€5k/week
Bareboat Catamaran Lucia 40
Lucia 40 · 2018
From
$6k/week
Bareboat Catamaran Leopard 46
Leopard 46 · 2010
From
$7k/week
Crewed Catamaran TIMAIAO 2
Lagoon 40 · 2009
From
$8k/week
Crewed Catamaran BUMBLEBEE
Lagoon 39 · 2016
From
$9k/week
Bareboat Catamaran Lagoon 52
Lagoon 52 · 2015
From
€9k/week
Bareboat Catamaran Bali 4.5
Bali 4.5 · 2019
From
$9k/week
Crewed Catamaran ALTITUDE ADJUSTMENT
440 · 2007
From
$9k/week
Other Vessel Types in Windward Islands
The Windward Islands chain stretches roughly 300 nautical miles from Martinique in the north to Grenada in the south, taking in St Lucia, St Vincent, the Grenadines, and Carriacou along the way. Unlike the more crowded Leewards, this arc of islands sits fully in the path of the north-east trade winds, which blow steadily at 15 to 25 knots through the season, making every passage purposeful and pleasantly swift. The Atlantic swell that wraps around the southern tips of the larger islands keeps things honest; this is a fleet that rewards sailors with a little confidence, though the inter-island legs themselves are rarely more than 20 to 30 miles.
The Grenadines in particular represent one of the finest compact cruising grounds in the Atlantic basin. Tobago Cays Marine Park, the salt pond anchorage at Petit St Vincent, and the yachtsman's village of Clifton on Union Island concentrate extraordinary variety into a stretch of water no larger than many European lakes. Charter here on a catamaran and you gain the draught advantage to anchor in turquoise shallows that monohulls must view from further out, alongside the deck space to host guests properly between passages.
Why Charter in Catamaran charter in Windward Islands
The trade wind corridor that defines Windward Islands sailing is unusually consistent by Caribbean standards. The north-east trades accelerate through the passages between St Lucia and St Vincent and again between Union Island and Grenada, producing reliable beam-to-broad reach sailing on most inter-island legs. Charterers with a genuine interest in passage-making rather than marina hopping will find the rhythm deeply satisfying: morning departures with full sails, sheltered anchorages by early afternoon, and evenings ashore in settlements that have not been entirely remade for tourism.
Each island carries its own distinct character shaped by colonial history and geography. Martinique retains a firmly French sensibility: boulangeries in Fort-de-France, Creole menus that treat rum as a gastronomic ingredient, and a marina infrastructure at Marin that is arguably the best-equipped in the eastern Caribbean. St Lucia combines this with a Creole-English culture and the iconic Piton mountains rising directly from the sea near Soufrière, an anchorage that has no real equivalent anywhere in the region. The independent nation of St Vincent and the Grenadines operates under its own entry regime, and the switch from island to island is accompanied by genuine changes in dialect, food, and pace.
For charterers who want to go beyond the Grenadines, Grenada's Grand Anse offers a proper provisioning stop, rum distillery visits at River Antoine (operational since 1785 and still water-powered), and a spice market culture that reflects the island's role as a major nutmeg producer. The northern tip of Grenada at Sauteurs provides a historically significant anchorage, and the boatyard community at True Blue Bay is useful for longer voyages heading south towards Trinidad and Tobago.
Catamaran charter in Windward Islands Highlights
Tobago Cays Marine Park, St Vincent and the Grenadines - a horseshoe of five uninhabited islets protected by Horseshoe Reef, offering some of the finest snorkelling in the eastern Caribbean over an intact coral ecosystem. Turtles feed in the shallows most of the year. Arrive early or late in the day to secure the best anchorage positions.
Soufrière Bay, St Lucia - moor on a buoy (anchoring is restricted to protect the reef) directly beneath the Gros and Petit Piton, with the sulphur springs and botanical gardens of the Sulphur Springs accessible by dinghy and a short taxi ride. The anchorage is exposed to southerly swell at times but the setting has no peer in the Windwards.
Bequia, St Vincent and the Grenadines - Admiralty Bay is one of the most sheltered deep-water anchorages in the region, the town of Port Elizabeth has a functioning boatbuilding tradition, and the Frangipani and Mac's Pizza are longstanding yachtsman institutions worth visiting for atmosphere as much as for food.
Clifton Harbour, Union Island - the commercial and customs hub of the southern Grenadines, with good provisioning at the Bougainvilla Market, strong WiFi, and the Anchorage Yacht Club as a practical stop before or after Tobago Cays. The snorkelling at Happy Island (a bar built entirely on a mound of conch shells) is a memorable detour.
Carriacou, Grenada - officially part of Grenada and carrying its own clearance requirement, but the boatbuilding village of Windward on the east coast is one of the last places in the Caribbean where wooden schooners are still constructed by hand using Scottish techniques brought over in the 18th century. Tyrrel Bay is a calm and well-equipped anchorage.
Marin Marina, Martinique - rather than treating this purely as a passage stop, charterers who spend a day here can access the broader Marin village market, the regional rum producers of the Sainte-Marie area to the north, and the uncommonly good provisioning options across several ship's chandlers and two well-stocked supermarkets.
Salt Whistle Bay, Mayreau - a tight, almost circular anchorage on the northern tip of Mayreau, the smallest inhabited island in the Grenadines. The beach curves around a grove of palms and the holding in sand is reliable in 3-5 metres. Limited and entirely appropriate for a quiet overnight stop before the Tobago Cays passage.
When to Sail
The Windward Islands sit south of the main Caribbean hurricane belt, giving them a longer and more reliable sailing window than the Leewards. The primary trade wind season runs from December through May, though June to August offers quieter anchorages and perfectly acceptable conditions for experienced charterers.
High Season (Jun-Sep)
Slightly counter-intuitively, summer in the Windwards is calmer in terms of anchorage crowding, though this is also the nominal hurricane season for the region. The Windwards sit south of the main hurricane tracks and have historically seen fewer direct hits than islands to the north, but charterers should carry appropriate insurance and keep a close eye on NOAA and the Caribbean Hurricane Network from August onwards. Winds ease to 12-18 knots through much of June and July, making the passages comfortable without being demanding. The Martinique Carnival and various Grenada festivals animate the islands during summer, adding cultural texture ashore.
Shoulder Season (May, Oct)
May is arguably the finest single month to sail the Windwards. The Christmas-to-April crowds have thinned, the trade winds are still blowing steadily, Tobago Cays is accessible without the flotilla density of January, and anchorage fees and provisioning wait times are noticeably shorter. October is a more cautious choice; the Atlantic hurricane season peaks in mid-September through mid-October, and while Grenada and the southern Grenadines sit south of the primary storm tracks, charterers should book with full cancellation cover and monitor conditions actively. The sailing itself, when weather systems are benign, is excellent: green and uncrowded.
Choosing the Right Yacht
Catamarans are not merely convenient in the Windward Islands; they are arguably the most practical hull form the destination demands. The majority of the finest anchorages, from the shallows inside Horseshoe Reef at Tobago Cays to the turquoise water over the Mayreau sandbar, sit in 2 to 4 metres of water, depths where a catamaran drawing 1.2 to 1.5 metres can anchor in positions that monohull keelboats simply cannot reach. The wide beam provides stable platform space for groups of up to twelve guests, and the twin-hull configuration eliminates the roll in the open roadstead anchorages that are common across the chain. Manufacturers well-represented in this fleet, including Lagoon, Fountaine Pajot, and Nautitech, produce models specifically engineered for trade wind sailing, with large roach mainsails and generous downwind sail area that makes the beam-reach passages between islands genuinely fast. Bali models are increasingly popular for charter groups who prioritise deck saloon living and social space; the flybridge variants offer exceptional visibility for navigating reef-strewn passages.
Eight Days Through the Grenadines, Martinique to Grenada
A suggested week-long charter route
Depart Marin Marina in the south of Martinique following a thorough briefing and provisioning. The 40-nautical-mile passage to Rodney Bay, St Lucia runs on a broad reach in the north-east trades. Arrive by early afternoon, complete St Lucia entry formalities at Rodney Bay Marina, and take the first evening ashore on the Rodney Bay strip.
Sail 25 nautical miles south along St Lucia's leeward coast to Soufrière Bay. Pick up a park mooring buoy beneath the Pitons. Afternoon ashore visiting the sulphur springs or the Fond Doux plantation estate for a rum and cocoa tour. Dinner on board at anchor with the Pitons silhouetted against the evening sky.
Early departure south for the St Lucia Channel, a 21-nautical-mile crossing to St Vincent that can produce a short steep chop when the trade winds are running hard against any northerly swell. Pick up pace through the passage, then bear away into Admiralty Bay, Bequia for a late-morning arrival. Afternoon in Port Elizabeth, with time to visit the model-boat workshop at Sergeant Brothers or walk the headland to Princess Margaret Beach.
A leisurely 18-nautical-mile reach from Bequia south to Mustique. Anchor in Britannia Bay, the principal anchorage on the west coast. Snorkelling off Macaroni Beach on the island's Atlantic side is reachable by water taxi. Mustique has no customs post; it is a St Vincent port of entry and requires no additional clearance for vessels already checked into SVG.
Tobago Cays day. Depart Mustique at first light for the 12-nautical-mile run to the Cays, entering through the northern channel between Baradal and Petit Rameau. Anchor in 3 metres of sand inside the reef by mid-morning before the day-trip boats arrive. Spend the full day snorkelling the reef and Turtle Sanctuary, with lunch on board. Overnight in the anchorage or move to Salt Whistle Bay, Mayreau for a quieter evening.
Pass through Clifton Harbour on Union Island to clear customs for the transit south to Grenada. Provision at the Bougainvilla Market. The 50-nautical-mile passage south to Grenada is the longest leg of the itinerary; the Kick 'em Jenny underwater volcano lies roughly 8 nautical miles north of Grenada and the designated avoidance zone of 1.5 kilometres should be respected. Arrive at Prickly Bay Marina on Grenada's south coast by late afternoon.
Carriacou detour optional: charter a local water taxi north to Tyrrel Bay for a day visit including Windward boatbuilding village, or spend the day exploring Grenada's south coast. The spice market in St George's town centre, the River Antoine rum distillery to the north-east, and Grand Anse beach are all viable day trips by taxi. Overnight at Prickly Bay or anchor off Grand Anse in settled conditions.
Final morning at anchor or a short sail to True Blue Bay for fuel and final provisioning. Complete Grenada departure formalities if continuing south towards Trinidad, or prepare the yacht for handback. A rum punch at the True Blue Bay resort bar has become something of a Windward Islands charter ritual; it earns its reputation.
Local Tips
- •Customs and immigration logistics across the Windwards require care. Each sovereign nation, including St Lucia, St Vincent and the Grenadines, Grenada (which includes Carriacou and Petit Martinique), and Martinique (French overseas territory), requires a separate check-in. Your SelectYachts broker will confirm current procedures, but budget time for Clifton or Kingstown clearance when moving from SVG into Grenada, as waiting queues can extend in high season.
- •Provisioning is best done at Marin in Martinique at the start of a northbound itinerary, or at Prickly Bay in Grenada for southbound departures. Both have genuinely good supermarkets with European-quality fresh produce, French and Grenadian cheese, and well-stocked wine selections. Provisioning in the Grenadines proper is limited; Clifton on Union Island covers basics but specialist items should be sourced at the larger hubs.
- •The Tobago Cays Marine Park fee is payable on arrival, currently collected by park wardens who come alongside by dinghy. The fee covers a defined period and anchoring outside designated sand patches within the park boundaries is prohibited. Dragging anchor onto coral carries serious fines; ensure your catamaran is properly set before leaving the helm.
- •Rum distillery visits are a legitimate part of the cultural itinerary rather than tourist window-dressing. River Antoine on Grenada and Depaz on Martinique (accessible from Le Carbet) both produce agricole-style rums with genuine terroir distinction. The Bequia tasting at the Frangipani bar is a more informal but worthwhile introduction to the locally beloved Hairoun beer and Vincentian rum brands.
- •Weather windows for the St Lucia and St Vincent channels deserve attention. Both passages are exposed to the full fetch of the Atlantic trades accelerating through gaps between the islands. Conditions are typically comfortable, but in the event of a passing low or unusually strong trade pulse, seas can build to 2.5 to 3 metres in the channels. An early morning departure generally catches calmer conditions before the daily thermal heating amplifies the breeze in the afternoon.
- •VHF channel 16 is the working hailing frequency throughout the Windwards, and the marina net at Rodney Bay (68) and the Grenada cruisers net (66) broadcast daily at 0730 and 0800 local respectively. These are practically useful sources of real-time anchorage conditions, weather forecasts, and local service recommendations from live-aboard cruisers who have been in the area for weeks.
Frequently Asked Questions
Do I need a sailing licence to charter a catamaran in the Windward Islands+
Is the Windward Islands route suitable for guests who have not sailed before+
What is the best base port for a Windward Islands catamaran charter+
How far in advance should I book a Windward Islands catamaran for peak season+
Are the Windward Islands safe from hurricanes during the season+
What size catamaran works best for a group of eight guests+
Speak with a SelectYachts broker to match the right catamaran to your Windward Islands itinerary and travel dates.
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