Windward Islands yacht charter guide: A luxury Caribbean island hopping itinerary from St. Lucia to Grenada & beyond

A jewel of the southern Caribbean, the Windward Islands offer some of the region’s most soulful and diverse cruising grounds. Situated in the Lesser Antilles in the eastern fringes of the Caribbean Sea, the Windward Islands benefit from a tropical climate year round and calm sailing conditions, while the local culture fuses French, British and Creole influences.

From the volcanic peaks of St. Lucia to the spice-scented air of Grenada and the tranquil cays of the Grenadines, on a bespoke Caribbean island-hopping itinerary, you can enjoy the islands as part of one seamless, indulgent journey.

Offering unmatched service on your Windward Islands yacht charter, Edmiston’s charter team can plot courses for the most beautiful private anchorages and arrange for curated experiences that allow you to make the most of these wonderful isles.

Your Windward Islands yacht charter itinerary: Discover the art of luxury Caribbean island hopping

St. Lucia: The iconic launch of your Windward Islands yacht charter

Known for its dramatic mix of dagger-like peaks, sugar-soft sands and turquoise seas, St Lucia is the ideal starting point for a superyacht charter in the Windward Islands. 

Anchor beneath the Pitons for an epic backdrop to your morning coffee, visit volcanic mud baths for a wellness experience like no other, and ask your crew to book the best tables at world-class restaurants like Jade Mountain.

Renowned for its rich cuisine which mixes the spices of the islands and its African and Creole heritage with European flavours, dining in St Lucia can be something of a cultural awakening, while its high-end resorts will leave you feeling fully pampered.

Plus, our expert charter teams can advise on what to do in St Lucia beyond the ordinary, from private tours of the island’s Morne Coubaril Estate to soaking up the authentic atmosphere of Gros Islet’s Friday night street parties.

St. Vincent: Volcanic landscapes and secluded bays

Made up of more than 32 cays and islands, St Vincent retains a sense of remoteness in places, an impression best discovered by private yacht charter.

Ask your captain to plot a course for places out of bounds to many, such as Cumberland Bay, a safe and secluded anchorage that offers easy access by tender to lush mountain treks where you can cool down beneath hidden waterfalls meanwhile, the nearby deep anchorage of Chateaubelair Bay is well suited to superyachts and offers superb snorkelling amid colourful coral reefs, as well as swift shore excursions to black-sand beaches. 

It’s also a great spot for superyacht guests looking to experience the utopia of Sandals St Vincent. At this resort where mountains meet the rainforest and sea, warm Caribbean hospitality has been honed to include 24-hour butler service in over-water villas and an elegant Japanese restaurant in Gatsu Gatsu. 

Other popular places worth weaving into your St Vincent yacht charter itinerary include a trek through banana and coconut plantations to the peak of La Soufrière volcano – the island’s highest point – and Wallilabou Bay, made famous by the ‘Pirates of the Caribbean’ films.

Your crew can also offer plenty of suggestions of what to do in St Vincent, off the beaten track, as we explore below.

Bequia, Mustique & Tobago Cays: Secluded jewels of the Grenadines

While St Vincent’s credentials as a jet-setting playground are well documented, there are many off-lying quiet Caribbean islands that can be reached on a yacht charter that still fly well below the radar.

The quiet charm of the little isle of Canouan, for example, still harks back to a simpler time on the isles, despite the easy access afforded by the Sandy Lane Yacht Club.

On a Grenadines yacht charter, guests can also discover the quiet allure of the isles of Mustique, Bequia and Tobago Cays, which each hum to its own rhythm of understated luxury.

Bequia is a gentle, lush island with a small main village made up of colourful wooden houses and plenty of local charm. Ease yourself into your exploration of the isles with a beach picnic here or a day trying out your yacht’s water toys in one of its beautiful bays.

For a touch more glamour, head to Mustique, a gorgeous private isle that has long been a haven for luxury travellers. Moor in Britannia Bay and tender ashore for Basil Bar’s exceptional banana pancakes before indulging in a rainforest facial at the serene spa within the island’s sole resort of Cotton House.

From here, it’s just a short hop to the quintet of uninhabited isles that make up the Tobago Cays where you can swim with the region’s diverse marine life in some of the clearest waters you have ever seen, before resurfacing for a sunbathing session on a deserted palm-fringed beach. Tobago Cays is also widely known as one of the best places for scuba diving in the Caribbean. 

Grenada’s gentle luxury: The essence of Caribbean refinement

The laid-back island charm of Grenada is hard to resist and is a must for your Windward Islands yacht charter, with marina access in St George’s on the west of the isle and anchorages such as Mount Hartman Bay on the south of the island.

Known as the spice island – you can often smell spices in the wind – Grenada is also an up-and-coming wellness and foodie destination, with Six Senses having recently opened its first Caribbean outpost here. 

The spa is spread out across a clutch of thatched cottages creating a calm atmosphere in keeping with the surroundings, while soundbaths will help you connect with the environment more fully.

At SeaFire restaurant, guests can dine on local ceviche and lobster against the soothing soundscape of the waves gently lapping the shore – an idyllic addition to your Grenada yacht charter.

For further ideas of what to do in Grenada, don’t miss a tour of the chocolate estates and spice plantations for which the isle is renowned and a diving adventure at the Underwater Sculpture Park.

Guests looking to extend their luxury yacht charter in Grenada can also plan a stop-off on her sister island of Carriacou, where you’ll find excellent seafood and crystal-clear waters.

Extending your Caribbean island-hopping itinerary: Martinique & Dominica

For those seeking to spend a little more time in the Windwards, an itinerary that includes the islands of Martinique and Dominica will allow you to fully embrace the magic of this island group.

Martinique – French elegance meets Caribbean soul

With pristine beaches, a sophisticated social scene and a little French refinement added to the boat-fresh seafood, Martinique is a perfect expression of island luxury.

Moor in Marina du Bakoua, where you can admire the incredible views of Fort-de-France Bay, one of the most beautiful bays in the world, from the thatched-roofed, stilted bar of the iconic Hotel Bakoua. It’s a great place to remind yourself of the simple pleasures a Caribbean yacht charter affords.

Alternatively, anchor near Anse A L’Ane and don’t miss lunch at La Maison De Li’let Oscar and a swim in the pools nearby – a favoured pastime of Napoleon’s wife Josephine, who grew up here.

Dominica – Seclusion and untamed beauty

Known for its elemental, raw appeal, Dominica is a land of mountains, hot springs and tropical rainforest that feels largely untouched by time. Some say that were Christopher Columbus to make landfall in the Caribbean once more, Dominica would be the only island he would recognise.

Anchor near Prince Rupert’s Bay and use your yacht as your luxurious base as you explore the island’s natural assets, from some of the best hiking in the Caribbean through its three national parks to its volcanic Boiling Lake and incredible dive sites. Don’t miss the panoramic views from lofty Champs bar – the perfect place to sip sundowners as the day drifts into evening.

Crafting your Windward Islands superyacht charter with Edmiston

On a superyacht charter in the Windward Islands with Edmiston you can expect experiences that transcend the normal Caribbean island-hopping itinerary.

From organising helicopter transfers to securing private island permissions and curated wellness days at the best spas in the Caribbean to onboard rum tastings, our expert charter teams will be on hand to ensure everything is plain sailing. Edmiston can also suggest luxury Caribbean events and festivals to add to your itinerary, and recommend some of the best restaurants in the Caribbean. 

Charter guests looking for some privacy on their Caribbean vacation will love the full-beam Master suite with its own terrace aboard AMIGOS, while the flexible accommodation on GRACE makes her a good choice for family charters.

Speak to Edmiston’s specialist charter team and start crafting your personalised Windward Islands yacht charter itinerary today.