Windward & Leeward

Category: Caribbean,

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The Windward’s and the Leeward’s embody all that is romantic and glamorous about the Caribbean. Forming the necklace that links the northern island to Trinidad, Tobago and South America, these are the quintessential West Indies.

This seven night Leewards itinerary is a charming mix of the exclusive and the laid-back; shanty settlements sitting side-by-side with the enclaves of the rich and rare.

Vibrant colours and pulsating music, perfect white sands and lush vegetation, wonderful Creole cooking and everywhere the unique scent of the region – a heady blend of nutmeg and spices; all delivered with that special Caribbean warm welcome and a flashing smile.


Day 1

Arrive Antigua airport and join the yacht in English Harbour. Antigua is softer than the volcanic neighbouring Windward’s, prompting Columbus to name the island in honour of a statue of the Virgin Mary de la Antigua in Seville. The crew welcome guests aboard and there is time to settle in before departing for a late afternoon passage to the French island of Guadeloupe. Arriving after dark the yacht anchors off a little fishing port.

Day 2

Awaking with a view of the tiny settlement of Deshaies, there is a chance to go ashore and sample this off-shoot of France in the West Indies. Guadeloupe is hardly the remote Caribbean with a population of 400,000 but this side of the island is peaceful and uncommercialised. The Maison du Bois and the Maison de Cacao are interesting museums of local life or, for the more active, the Trace des Contrabandiers is a three hour walk along a ancient smugglers route across the mountains – a section of which is quite do-able before setting out for the volcanic Iles des Saintes, twenty miles to the south.

Day 3

Overnighting in the tranquil harbour of Bourg on Terre-de-Haut, more locally known as le Village, the lush vegetation forms a silent almost magical backdrop to the half dozen streets of attractive Creole houses and waterfront cafes populated with local fishermen. A tad touristy, the town is beautiful to explore before the day trippers arrive and an encouragement to sail mid morning for the unspoilt island of Dominica. A jumble of peaks and spurs, it has its own lush, super-fertile microclimate where a banana tree shoot planted directly into the ground will be fruiting six months later. Overnight in Portsmouth, a sleepy port far from the and commercialism of the capital Roseau.

Day 4

After a morning visit ashore, a four hour steam over lunch take the yacht to the island of Martinique where the air pulses to the Caribbean beat of zouk. Fort de France is a sophisticated city of 100,000 with plenty to offer but for the real French Caribbean the yacht heads to the south west of the city and three cracking beaches near the charming sleepy village of Les Anses d’Arlet where a few delightful beach bars and sheltered waters make a terrific place to drop the anchor.

Day 5

Following the C18th war cry “To St Lucia, to St Lucia”, an early morning start heads south over a sparkling sea to the “friendliest island in the Caribbean”. The north-west corner is the more developed but there are some lovely beaches around Gros Islet where the sand is so soft you stumble walking. A morning swim and a wander after breakfast then south to Soufrière and the Pitons, visual symbol of this beautiful corner of paradise. Boasting the world’s only “drive-in volcano”, the well-behaved Sulphur Springs make an interesting place for a short, if somewhat odorous, visit. It is a relaxing twenty five mile passage in the late afternoon to the delightful Grenadines.

Day 6

St Vincent and the Grenadines are a wonderful combination of sophisticated yet discreet luxury and real Caribbean charm; perfect sailing grounds to explore by yacht. South lie the delightful Bequia and Mustique. Beloved of the late Princess Margaret, the private fiefdom of Mustique is wonderfully relaxed, the “resident” úber-rich being indistinguishable from the beach and yacht bums that inhabit Basil’s Bar. Further down this beautiful island chain lie Mayreau and Canouan; lovely spots with tranquil hidden coves to anchor overnight.

Day 7

If not too crowded with day visitors, the five uninhabited Tobago Cays can be a peaceful anchorage for a relaxing late breakfast and swim en route for Petit St Vincent, the quintessential old-fashioned Caribbean. No phones, TV or sophisticated communications, guests at this luxurious island resort communicate by flag and doing nothing is actively encouraged. An afternoon sail takes the yacht to Carriacou with the remote dream beach of .Anse la Roche. The island is almost horizontally laid-back and a great last night stop. Worth sampling the disarmingly strong local “jack-iron”; it has the unnerving distinction of allowing ice to sink in the glass!

Day 8

An early morning departure for the nutmeg isle of Grenada and international connections home.

To enquire about this destination or to discuss creating your bespoke dream holiday, please get in touch.

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