Windward Islands Yacht Charters

The Windward Islands form the southeastern boundary between the Caribbean and the Atlantic Ocean. This fabulous Windward group of islands stretch from the southern island of Grenada up north to Martinique and include St. Lucia, St. Vincent and the Grenadines along the way. They were named the Windwards in the early 18th Century by the British, who’s colony cruise ships frequently had to rely on the trade winds to reach them. These often delivered them to the edge of the Caribbean Sea near Dominica and Martinique. The Windward Islands were named because they were more windward at this location than the Leeward Islands.

Find the perfect yacht for your Charter Yacht holiday in the Windward Islands in the Caribbean!



The island of Grenada is also known as the ‘Isle of Spice’ and is located on the southern end of the group of Windward Islands. Grenada is often a starting or end point for a charter yacht itinerary. From the amazing food to Natural Parks, and everything in between, Grenada is a tropical playground that delights all the senses!

On the weekends the locals set up street barbecues and cook the most delicious jerk chicken and bbq pork, a treat not to be missed. Open-air bars and marina-side restaurants are a favorite for locals and tourists alike, to hang out and enjoy the scenery, or watch the glorious sunset. The culinary delights ranging from sidewalk street food to 5 star fine dining make Grenada an ideal island for leisurely charter yacht stopover.

But it doesn’t stop there, for the more energetic, trail running (or ‘hashing’) is a popular exercise and many guided trails are available to link up with. Slower paced hiking is a popular alternative with breathtaking scenery, majestic waterfalls and spectacular flora and fauna specimens to intrigue.

Scuba diving and, or snorkeling is an absolute must as the reefs around this island are world-class. For those keen on exploring the culture and trade of the island, a visit to the historical cocoa plantations is a highlight, and the tour finishes with a chocolate tasting to-die-for. The oldest working water-propelled rum-distillery in the Caribbean resides on the island of Grenada.

From a conservation point of view, if you are lucky enough to time your visit to Grenada with the leather-back turtle’s nesting season, you could witness their sunset migration onto the shores to lay their eggs, quite a sight to behold!

Grenada Leeward Island Caribbean
Grenada Leeward Island Caribbean Things to do
Grenada Leeward Island Caribbean Yacht Charters

St Lucia

The beautiful island of Saint Lucia covering 238 square miles is located north/northeast of the island of Saint Vincent, northwest of Barbados and south of Martinique. It has a population of just over 180,000 and the capital city is Castries located right in the heart of the island.

St Lucia is an island destination that is not only literally weather perfect all year round, but also boasts a thriving social calendar! The end of the year (December) is celebrated with the festival of lights where St Lucians honor their patron saint Lucy after whom St. Lucia was named. The Jazz Festival happens in May which brings musicians from all around the world. In the mid-month of July, the streets come alive with soca and steel pan music as the country sets into their carnival season. August is chocolate heritage month, so if you have a sweet tooth, this is something to look forward to, and in October the Creole/French heritage is celebrated with street stalls, markets, and restaurant specials.

The Pitons, a UNESCO World Heritage Site since 2004, are a couple of mountainous volcanic plugs that jut out from the shoreline into the sky creating an extraordinary vision that is both uniquely mesmerizing and beautiful. Petit and Gros Piton are just under and just over 2,500 feet respectively and cover nearly 3,000 square hectares of land. Linked to the Piton Mitan range of mountains, The Pitons are both a glorious vista and a fascinating hiking choice.

The inactive yet ‘live’ volcano situated at the Sulphur Springs Park is a popular activity for locals and visiting tourists alike. The park offers mud baths that leave the skin feeling rejuvenated and the body energized.

St Lucia Leeward Island Caribbean Yacht Charters
St Lucia Leeward Island Caribbean Yacht
St Lucia Leeward Island Caribbean Charter Yacht

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Sample Itinerary for the Windward Islands

Starting in Antigua, one of the Leeward Islands in the Caribbean region and the main island of the country of Antigua and Barbuda, this 10-day itinerary sails explores the southern Windward islands and ends in glorious St Vincent.

After arriving in Antigua, and being transported to your charter yacht, you will be met by your crew and welcomed aboard with a delicious refreshing Caribbean beverage. A safety and orientation briefing will be given before setting sail to a nearby cove where lunch will be served. Enjoy the afternoon swimming, snorkeling and settling in to the laid back island flow. Late afternoon we will arrive at English Harbour, a Caribbean sanctuary, rich in maritime significance and naval history. The main entrance to the protected natural harbour is flanked by fortresses on either side, transporting you back in time to the 18th century when the Royal Navy’s Caribbean fleet was first established there.

Not far from Nelson’s Dockyard, English Harbour has plenty to offer travelers of all kinds including an array of bars and restaurants, and an English pub that offers a British menu with a Caribbean twist. There is also duty-free shopping, a museum highlighting the local history of the land, and “jump up” steel band sessions that will have you bopping and clapping along.

Spend the day relaxing, exploring the charm of English Harbour a little further, or take a walk to Falmouth Harbour for a horse ride on the beach. If you’re still up for some water activity, there is plenty to be had, from diving to snorkeling, swimming or kite surfing. You will not be bored as there is plenty to see and do at this end of the island.

After a delicious breakfast, we will set sail for Guadalupe’s Deshaies. The charming traditional fishing village also offers good eating and drinking options and there’s a pretty little beach framed by green hills all around. You will have a chance to visit the local market and take a walk around the quaint town. Deshaies is a working fishing port, so the best beach for swimming and sunbathing is at nearby Grande Anse.

Later in the day, we will set sail for Basse-Terre, where we will drop our anchor and enjoy the scenery. Basse-Terre is a glorious sight as it boasts soaring peaks, including the active La Soufrière volcano, and is by far the more dramatic of Guadeloupe’s two main islands. The center of Basse-Terre is covered in thick rainforest and makes up the impressive Parc National de la Guadeloupe.

The underwater landscape here is equally as impressive as the sheltered, calm waters of this protected marine national park delight divers and snorkelers with reefs rich in tropical fish and coral reefs. This would also be a great jump off point for any land-based activities such as hiking the rain forest, or enjoying one of Grande-Terre’s white-sand beaches, flanked by small seaside hamlets loaded with local charm.

Today we will sail to the southern tip of Guadeloupe. We will enjoy a delightful tiny anchorage right next to the Vieux-Fort Lighthouse. Built in the mid-1950s, the lighthouse marks the entrance of the Basse-Terre bay and the end of Les Saintes Passage and creates a fabulous opportunity for exploration.

Off the southern coast of Guadeloupe, a cluster of eight small islands known as the Iles Des Saintes lures sailors and travelers seeking the ultimate in off-grid Caribbean charm. The largest, Terre-de-Haut, features a picture-perfect seaside village where sidewalk cafes and small boutiques overlook a bay that has been recognized as one of the most beautiful in the world. With very few cars on the island, the most popular mode of transportation are solar-powered electric golf carts, moped, or simply walking. Nearby Terre-de-Bas provides an even quieter escape, with deserted beaches and miles of walking trails. Other islands in the group are left to the birds, iguanas and visiting yachts, which drop anchor in quiet bays.

Today we set sail for Dominica. Dominica is a mountainous Caribbean island nation. Morne Trois Pitons National Park is home to the volcanically heated, steam-covered Boiling Lake. The park also encompasses Sulphur vents, the 208 ft. tall Trafalgar Falls and narrow Titou Gorge. To the west is Dominica’s capital, Roseau, with colorful timber houses and botanic gardens.

Lush mountain peaks lined with popular hiking trails soar to nearly 5,000 feet. And beneath the waters, diving the dramatic vertical walls of underwater terrain is equally as impressive.
The Indian River flows to the Caribbean Sea between the town of Portsmouth and the village of Glanvillia. It is the widest river in Dominica and boat rides are a popular attraction.

After breakfast and a refreshing dip, we take a short sail south to the northern side of Martinique. Volcanic in origin, Martinique is a mountainous stunner crowned by the still-smoldering Mont Pelée, the volcano that wiped out the former capital of St-Pierre in 1902. Offering a striking diversity of landscapes and atmospheres, Martinique is a cosmopolitan and sophisticated island that boasts incredible beaches, superb hiking, top-notch culinary experiences, as well as an enormous array of activities and rich cultural life.

Martinique’s lively capital, Fort-de-France Bay is safe and friendly for a walking tour, and must-see stops include the Schoelcher Library. Shops and restaurants are fun to explore. The town’s namesake fort still looms imposingly, and an ancient savanna marks the heart of the city. The highlight of any visit is a stop at the bustling Covered Market, full of vendors selling unusual tropical produce, local handicrafts, and baked goods.

If you’re looking for bars, casino action, golf, decent dining, and watersports all in one location, head to the tiny marina village of Trois Ilets. The Hotel Bakoua and other resorts are located here, making it a great base for walking to the local shops or taking the cheap ferry across to Fort de France.

Another short sail southwards will lead us to St Lucia, an Eastern Caribbean island nation with a pair of dramatically tapered mountains, the Pitons, on its west coast. On land, St Lucia offers hiking trails through the impressive rainforest that lead to waterfalls like the 48 ft-high Toraille, which pours over a cliff into a garden.

Below the surface, diving in Saint Lucia offers a world-class experience with the island ideally situated between the Caribbean Sea and the Atlantic Ocean and offers more than 22 awe-inspiring dive locations.

Saint Lucia cuisine is an eclectic mix of American, European, Indian and Caribbean flavors. The signature meal you should have in Saint Lucia is green figs and salt fish, the island’s national dish. Locals boil unripe bananas and then add salt-cured boiled or flaked cod. It’s a hearty dish made with various herbs and spices. Pair this meal with a plate of fried plantains, a bowl of callaloo soup (a spinach-like soup made from the callaloo plant), or a side of breadfruit. Breadfruit is a staple of Saint Lucia cuisine and resembles a potato, except with a sweeter flavor. Try these local favorites individually or bring them all together on a delicious platter!

From St Lucia we sail to Saint Vincent, the largest island of Saint Vincent and the Grenadines, which comprises 32 islands and cays.

Saint Vincent is composed of partially submerged volcanic mountains, so it is blessed with mountainous and lush landscapes, tumbling waterfalls, verdant rainforests, volcanic-rich soil with unspoiled backdrops of brilliant flora, alluring crystal clear waters with magnificent coral reefs and an active volcano, called La Soufrière, the majority of the beaches on the mainland have black sand.

An early start this morning as we set sail stopping to check out Mayreau, a small inhabited island with a population of just over 270. Onwards we sail to the beautiful Tobago Cays which are an archipelago comprised of five small islands and extensive coral reefs. The cays – Petit Rameau, Petit Bateau, Baradal, Petit Tabac and Jamesby are amongst the world’s most breathtaking anchorages. The anchorage is protected by an enormous horseshoe reef which also provides incredible snorkeling. You can swim in a turtle sanctuary with the turtles that feed around the five islands or explore ashore with the iguanas and tortoises. In the evening your crew can arrange a wonderful lobster or fish beach BBQ with one of the local guides and dine under the stars with the sand between your toes.

We set off after breakfast for Grenada where we will anchor close to Halifax Harbour for the evening. Spend the afternoon enjoying some watersports, or go ashore to explore this part of the island which falls under the protection of the Marine Park.

Later in the day, we will sail around to Grand Anse Bay to anchor for the evening.

Otherwise known as The “Isle of Spice”, Grenada has a lot to offer and For those keen on exploring the culture and trade of the island, a visit to the historical cocoa plantations is a highlight, and the tour finishes with a chocolate tasting to-die-for. The oldest working water-propelled rum-distillery in the Caribbean resides on the island of Grenada.

It is one of the most spectacularly beautiful islands of the Caribbean with lush rain forest, waterfalls, old plantations, and sensational beaches. There are many hiking trails around the island – from easy half-hour hikes to a waterfall to arduous all-day hikes to the island’s highest point Mt St Catherine. The town of St George’s is regarded as the most picturesque capital in the Caribbean.

Open-air bars and marina-side restaurants are a favorite for locals and tourists alike, to hang out and enjoy the scenery, or watch the glorious sunset. The culinary delights ranging from sidewalk street food to 5-star fine dining make Grenada an ideal island for leisurely charter yacht stopover.

Scuba diving and, or snorkeling is an absolute must as the reefs around this island are world-class.

We will stay anchored at Granada Grand Anse Bay for another night where we will enjoy our last evening together on your charter yacht before wishing you well, until the next time we see you!

Please note, this is a sample itinerary designed to whet your appetite and by no means depicts your expectations or limits available options. Crewed Charter Yacht Vacations will work with you to ensure your IDEAL itinerary is finalized.