Windward Islands Charter Itinerary

Windward Islands Charter Itinerary

As one of the highlights of the Caribbean, the Windward Islands are perfect for exploring from your own luxury charter yacht

The Windward Islands are the southern islands of the lesser Antilles that lie within the West Indies and are a true tropical paradise, with vibrant blue waters, lush rainforest, volcanic landscapes, white sands and incredible scenery both above and below the waves. 

A seven-day charter will help you enjoy the highlights of this stunning area, and create your own magical Caribbean memories.

Day 1 - Antigua

Start your Windward Islands charter in beautiful Antigua. Bustling with activity, you’ll be spoilt for choice when exploring the island – once a hotspot for pirates, today it is one of the busiest of the Windward Islands and offers an alluring blend of history and laid back Caribbean charm. 

With more than 54 miles of coastline, there are countless idyllic beaches to choose from and your crew can recommend the best secret spots. Follow in the footsteps of Nelson and explore the historic dockyard at English Harbour, before cruising to Nonsuch Bay to spend an afternoon enjoying your yacht’s water toys. After dark, come ashore and party if you fancy sampling Antigua’s bustling nightlife.

Day 2 - Anguilla

After the energy of Antigua, Anguilla is the perfect antidote. With its low-key elegance it is the perfect spot to indulge in some relaxation. Sample one of the island’s spas or sunbathe in the tropical beauty of one Anguilla’s 33 beaches – don’t miss Rendezvous Bay, reported to be the most beautiful beach in the world!

Finish your day with a fresh local rum cocktail while watching one of Anguilla’s legendary sunsets. The marina is another popular spot, home to elegant seafood restaurants and lively cocktail bars.

Day 2 - Anguilla

Day 3 - Guadaloupe

Guadaloupe is an archipelago of 12 islands naturally arranged in a butterfly shape. Meander between the different islets and choose your perfect anchorage. 

There is excellent diving, particularly in Jacques Cousteau’s Underwater Reserve which is a must do. Come ashore and hike the abundant rainforest or enjoy a picnic on one of the many deserted beaches.

Day 4 - Dominica

Paddle up the Indian River and marvel at the impressive swamp bloodwood trees that flank the river’s edge. Or why not explore the Cabrits National Park and immerse yourself in some of the rainforest? 

Dominica is known for its incredible dive spots so diving fans won’t want to pass up the chance to explore its underwater world before enjoying a welcome dinner on board your yacht.

Day 4 - Dominica

Day 5 - Martinique

Martinique is the largest of the Windward Islands, and was discovered by none other than Christopher Columbus in 1494. This volcanic island has a unique French-Caribbean vibe and delivers laid back luxury. 

Explore the villages, which offer boutique shopping, plenty of culture and mouthwatering cuisine, and sample the local produce at the Grand Marche market. Stroll to the Pointe du Bout beach, which has the feeling of a tropical lagoon, or dive the island’s many reefs and wrecks.

Day 6 - St Lucia

The quintessential Caribbean dream, St Lucia is a postcard-perfect island that has retained its charm even as its popularity has grown. This small island offers something for everyone with a warm welcome wherever you go, mountainous landscapes and lush forests filled with color. 

Exploring the island by foot is a must, with a wide variety of trails – a highlight is the Soufriére trail that takes you into the crater of the Soufriére volcano. Treat yourself to a mud bath and private mineral bath at the Diamond Falls Botanical Gardens spa afterwards. Anchor up in Marigot Bay and enjoy your last night on board with a special meal and sunset champagne.

Day 6 - St Lucia

Day 7 - St Lucia

Finish off your Windward Islands charter by enjoying one final dive – with an abundance of sea life in the area you’re sure to see something new. Take a last wander around the island before bidding farewell to your yacht.

My Enquiry List

Your Enquiry List is Empty
Selected Yachts for Sale
Selected Yachts for Charter
Send us your Enquiry
Thank you!
We have successfully received your enquiry and will be contacting you shortly with more information related to your request.