Motor Yacht Charter Leeward Islands
From Antigua's English Harbour to the calm anchorages of St Kitts and Montserrat, the Leeward Islands reward motor yacht charterers with short inter-island passages, consistent trade winds, and a concentration of world-class marinas rarely matched in the Caribbean.
Motor Yachts Available in Leeward Islands
Browse our selection of motor yachts available for charter in Leeward Islands.
Crewed Motor Yacht Princess V55
Princess V55
From
€4k/week
Crewed Motor Yacht VanDutch 55
Van Dutch 55 · 2013
From
€4k/week
Crewed Motor Yacht Princess V65
Princess V65
From
€5k/week
Crewed Motor Yacht Princess V70
Princess V70 · 2006
From
€5k/week
Crewed Motor Yacht Mochi Craft 74- Day Charter
Mochi Craft 74 · 2006
From
€7k/week
Crewed Motor Yacht Broward 100
Broward 100 · 2004
From
€9k/week
Luxury Crewed Motor Yacht SORANA II
Princess 82 · 2018
From
$35k/week
Luxury Crewed Motor Yacht LEXINGTON
Horizon 25 · 2006
From
$40k/week
Luxury Motor Yacht SOVEREIGN
Burger 97 · 1966
From
$48k/week
Luxury Crewed Motor Yacht SOUTHERN BELLE
Johnson 87 · 2006
From
$54k/week
Crewed Motor Yacht ISLAND GIRL
Westport 112 · 2001
From
$55k/week
Luxury Crewed Motor Yacht PURA VIDA
Moonen 98 · 2009
From
$64k/week
Luxury Crewed Motor Yacht THE PEDDLER
Dreamline 26 · 2019
From
$69k/week
Fishing Boat REEL TIGHT
Merritt 86 · 2017
From
$70k/week
Crewed Motor Yacht ANGELEYES
Horizon FD85 · 2017
From
$75k/week
Luxury Crewed Motor Yacht DATE NIGHT
Ferretti 920 · 2018
From
$75k/week
Luxury Crewed Motor Yacht AQUA LIFE
Horizo FD87 · 2020
From
$75k/week
Luxury Crewed Motor Yacht ALANDREA
Custom Line 108 · 2016
From
$75k/week
Luxury Crewed Motor Yacht SYNERGY
Sunseeker 68 · 2017
From
$80k/week
Luxury Crewed Motor Yacht TEMPTATION
Palmer Johnson 123 · 2007
From
$80k/week
Luxury Motor Yacht CRESCENDO IV
Delta Marine 122 · 1997
From
$80k/week
Luxury Crewed Motor Yacht SEA OWL
Azimut Grande 27M · 2022
From
$80k/week
Luxury Crewed Motor Yacht SEAQUEST
Westport 130 · 1999
From
$85k/week
Luxury Crewed Motor Yacht LAILA
Sanlorenzo SD90 · 2023
From
$90k/week
Other Vessel Types in Leeward Islands
The Leeward Islands stretch from Anguilla in the north to Dominica in the south, taking in Antigua and Barbuda, St Kitts and Nevis, Montserrat, and Guadeloupe along the way. The distances are genuinely manageable under power: Antigua to St Kitts runs roughly 65 nautical miles, St Barts to St Martin barely 15. A motor yacht covers these passages comfortably in half a morning, leaving the rest of the day for the destination rather than the transit.
What distinguishes this arc from the more southerly Windwards is the character of each island. British colonial heritage sits alongside French departmental administration, Dutch free ports, and volcanic landscapes untouched by mass tourism. Provisioning standards in Antigua and St Martin are genuinely excellent, which matters when you are feeding guests at the level this fleet demands. The sailing infrastructure, from Falmouth Harbour to Gustavia, is correspondingly sophisticated.
Why Charter in Motor Yacht charter in Leeward Islands
The Leeward Islands operate under the north-easterly trade winds that blow with notable consistency between December and June. For motor yachts, this means predictable sea states and passage planning that rarely requires significant revision. The Atlantic swell that affects more exposed coastlines is largely absorbed by the island chain itself, so leeward anchorages stay calm even when the windward shores are lively.
The range of anchorages and ports of call is exceptional. Gustavia in St Barts functions as an haute-cuisine destination with provisioning to match its superyacht clientele. English Harbour and Falmouth Harbour in Antigua offer full marina services alongside a density of maritime history that few Caribbean ports rival. The almost deserted beaches of Barbuda's western coast provide genuine solitude within half a day's run from Antigua.
Guadeloupe adds a dimension that purely English-speaking itineraries miss. The Îles des Saintes, a cluster of eight islets south of Basse-Terre, are visited by relatively few non-French charterers despite offering some of the clearest water and most characterful fishing villages in the entire Lesser Antilles. Running a Leeward Islands itinerary that dips into French waters adds variety that guests remember.
Motor Yacht charter in Leeward Islands Highlights
English Harbour and Falmouth Harbour, Antigua - the twin-basin hub of Eastern Caribbean yachting, with full superyacht services, chandleries, and Nelson's Dockyard as a UNESCO World Heritage backdrop.
Gustavia, St Barts - compact, expensive, and genuinely well-provisioned; the harbour wall is shallow for larger yachts but mooring buoys and short anchor runs make it workable for most motor yachts under 50m.
Grand Case, St Martin - a single road lined with serious restaurants operating out of modest premises; the food-to-decor ratio is one of the best in the Caribbean and worth a dedicated lunch anchorage.
Îles des Saintes, Guadeloupe - Terre-de-Haut's Bourg des Saintes has the feel of a Breton fishing village transported to the tropics; the anchorage in the Baie des Saintes is well-protected and visually distinctive.
Pinney's Beach, Nevis - a long arc of calm water off the Four Seasons waterfront; tender access is easy and the anchorage is rarely crowded outside high season.
Barbuda's Coco Point and Palmetto Point - arguably the finest beach anchorages in the Leewards, with near-deserted white sand and turquoise shallows that contrast sharply with busier Antigua just 30 miles away.
The Narrows, St Kitts and Nevis - the two-mile channel between the sister islands offers calm water, photogenic scenery, and a natural passage stop that few itineraries skip.
When to Sail
The Leewards have a well-defined high season aligned with the Caribbean winter, running from December through April, when trade winds are settled and rainfall is at its annual low. The Atlantic hurricane season officially runs June through November, though June and November themselves carry relatively limited risk.
High Season (Jun-Sep)
Note that for the Leewards, the true high season is December to April, not summer. During June to September, the trade winds soften and seas flatten, which suits motor yacht passages well. Rainfall increases and humidity rises, and the statistical risk of tropical storm activity is real from August through October. Rates are lower, marinas have availability, and crowds in Gustavia and English Harbour are noticeably thinner. Charterers who are flexible on timing and vigilant on weather routing can find excellent value.
Shoulder Season (May, Oct)
May sits just before the humidity builds and represents perhaps the best-value window for quality conditions: trade winds still present, seas reasonable, peak-season crowds gone. October is more variable and requires careful monitoring of tropical weather systems. Some marinas run reduced services. Both months reward charterers who are willing to stay nimble with their programme.
Choosing the Right Yacht
Motor yachts dominate charter in the Leewards for good reason. The inter-island passages are short enough that range anxiety is irrelevant, and the consistency of flat-water leeward anchorages suits displacement and semi-displacement hulls equally well. Larger motor yachts in the 30-40m range gain particular advantage here: the marinas at Falmouth Harbour and Gustavia can accommodate serious beam, and the space for water toys, a proper tender garage, and guest cabins makes a meaningful difference on a one- or two-week programme. Azimut and Sanlorenzo hulls in the 28-35m range offer an excellent balance of speed, economy, and liveability for groups of six to ten guests. If the itinerary extends to Guadeloupe or involves sustained running between islands on consecutive days, semi-displacement designs with range above 800 nautical miles are worth prioritising.
Seven Days Through the Northern Leewards from Antigua
A suggested week-long charter route
Board in Falmouth Harbour, Antigua, and allow the afternoon for provisioning and settling in. Dinner at anchor in English Harbour, where the 18th-century dockyard forms an unusual backdrop to the evening.
Depart north-west for Barbuda, approximately 30 nautical miles. Anchor off Coco Point or Palmetto Point on the west coast. The reef snorkelling is accessible by tender, and the pink-tinged sand warrants an afternoon ashore.
Run north to St Kitts, roughly 70 nautical miles. Arrive at the southern tip and anchor off Cockleshell Bay for lunch before moving into Basseterre port if clearance and marina berth have been pre-arranged. The St Kitts Scenic Railway makes a worthwhile afternoon excursion.
A short 12-nautical-mile run brings you to Nevis. Anchor off Pinney's Beach for a morning swim. Afternoon, take the tender ashore and arrange horses or a jeep tour up to the volcanic crater rim on Nevis Peak.
Head north-east to St Barts, approximately 55 nautical miles from Nevis. Clear into Gustavia and take a mooring buoy if a berth alongside is unavailable. The afternoon is best spent walking the port and arranging dinner reservations at Eden Rock or any of the hillside restaurants above the harbour.
A 15-nautical-mile run east into St Martin/Sint Maarten. The French side village of Grand Case merits a lunch stop by tender. Simpson Bay Lagoon offers a sheltered overnight anchorage, and Maho Beach provides the unusual spectacle of low-altitude aircraft arrivals for those interested.
Return south-east to Antigua, approximately 110 nautical miles, best run early to arrive by afternoon. Final night at anchor in the protected waters of Deep Bay off St John's, with a return to Falmouth the following morning for disembarkation.
Local Tips
- •Customs and immigration are handled island by island in the Leewards, and each nation requires its own clearance paperwork. Between French St Martin and Saint-Barthélemy you move freely within EU territory, but crossing to Anguilla (British) or St Kitts (independent) requires full check-in. Appoint a local agent in each port for charters covering multiple jurisdictions.
- •Provisioning from Antigua is the most efficient base in the northern Leewards. Budget Marine in Falmouth carries serious chandlery stock. For high-end provisions and wine, Gourmet Basket and the supermarkets along the Falmouth Road can be supplemented by deliveries from specialist importers given adequate notice.
- •French customs apply in Guadeloupe, Saint-Barthélemy, and the French side of Saint-Martin, which means EU VAT rules on charter yachts are relevant if your vessel is EU-flagged. Non-EU flagged yachts have different obligations. Confirm the fiscal status of your charter yacht before finalising a programme that enters French waters.
- •The Leeward Islands Marine Association (LIMA) publishes updated anchoring regulations, particularly around marine protected areas near Antigua and Barbuda. Several popular anchorages have restricted or prohibited areas that have changed in recent years. Download current charts rather than relying solely on older cruising guides.
- •Local cuisine worth seeking out ashore includes Antiguan pepper pot and ducana (a sweet potato dumpling), the Creole preparations in Guadeloupe's village restaurants, and the lobster caught off Barbuda which often appears on local menus at prices that reflect supply rather than marketing. Avoid the resort waterfront for these; they are found in village-centre spots.
- •Moorings and anchorages fill quickly around Antigua Sailing Week (late April to early May) and during the Classic Yacht Regatta. These events bring significant vessel traffic and crew. If your charter falls adjacent to these dates, either embrace the spectacle or move the itinerary south towards Nevis and Guadeloupe, which remain quiet.
Frequently Asked Questions
What is the typical passage time between islands under motor power+
Are large motor yachts above 40 metres able to berth in the main ports+
What are the sea conditions like for guests who are not experienced sailors+
Is the Leeward Islands region suitable for year-round chartering+
What are the snorkelling and diving options accessible from a motor yacht+
Do I need a local captain or can I bring my own licensed crew+
Speak to a SelectYachts charter specialist to build a Leeward Islands programme around the right vessel, the right dates, and the anchorages that will actually make the week.
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