Windward Islands Yacht Charter, Caribbean
Martinique, St Lucia, St Vincent, Grenadines, Barbados, Grenada, Trinidad and Tobago
A crewed yacht charter in the Caribbean would not be complete without a visit to the Windward Islands. Located on the southern end of the Caribbean chain, the Windward Islands are the Caribbean's best-kept yacht charter secret. These lush and richly tropical volcanic islands are a little piece of France, floating amongst the palm lined sandy beaches and misty rain forests, of the Caribbean. The Windward Islands yacht charter area are so named due to being on the windier and wetter side of the Lesser Antilles and consist of Martinique, Saint Lucia, Barbados, Saint Vincent and the Grenadines, Grenada Trinidad and Tobago. Together all the islands make up the group of Caribbean islands known as the Lesser Antilles.

This jewel area of the Caribbean hosts yachting year-round, with a rainy season from July through October. From its distinctive cuisine to its language, The Windward Islands exude the ambiance of Paris with the warmth, friendliness and spice of the West Indies.
As with most of the Caribbean, The Windward Islands yacht charter season runs from November through to July. The Caribbean's primary high season is from mid-December to March, when the winter escapees from North America and Europe arrive in their greatest numbers. The hurricane season is from late July to early October. Although hurricanes are generally rare, this is still the least expensive time for chartering in the Caribbean and there are some really good deals available - however, as well as running the risk of storms, this time of year also tends to be associated with lighter (or non existent) winds.
The types of yacht charters available for a vacation in the Windward Islands are all the main types including motor, sailing, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and superyacht charters.
Martinique is the largest of the Windward Islands yacht charter area. Known as Madinina, or Island of Flowers, Martinique, is renowned for its scenic beauty. The 425-square-mile island is speckled with plantations producing guavas, mangos, papayas, bananas, pineapples, sugar, cinnamon and coffee and is home to countless varieties of plants, trees and flowers including hibiscus, frangipani, bougainvillea, poinsettias and nearly 100 species of orchid. Martinique is a French overseas territory and has strong French influences with Parisian style bistros and quaint narrow streets. The island of Martinique has several ship wrecks to dive and plenty of sites to visit including the islands volcano Mt. Pelee, a trio of stunning coves at Les Anses-d'Arlets and the towering fortress of Diamond Rock.

St Lucia is the sort of tropical paradise that a yacht charterer dreams about, with white sand beaches framed by the dramatic Atlantic Ocean on the east, and the calm Caribbean waters to the west. A St Lucia yacht charter offers some of the finest scenery in the Caribbean including St Lucia's twin Pitons that tower 2000 feet over lush rainforest delightfully spotted with colored flowers, ancient ferns and exotic wildlife, interrupted only by plantations of tropical fruit. The geography of St Lucia creates a fantastic environment for outdoor activities of all kinds. Steep coastlines and beautiful reefs offer excellent diving and snorkeling. Island waters are an anglers dream, filled with king mackerel, barracuda and white marlin.

Saint Vincent is a volcanic island featuring a 3,000 foot volcano named Soufriere. Mountainous, covered in tropical greenery, there are no white sand beaches on this island, a stark contrast to the amazing pure white beaches found further South in the St Vincent and Grenadines island chain. The lack of beaches however, does make this island unique as it has remained largely unspoiled by the more commercial style of tourism. The interior of the island is largely undeveloped, with no roads crossing the island.
The Grenadine Islands, until recently, were one of the Caribbean's best-kept yacht charter secrets. The Grenadines are headed by St Vincent and consist of 32 islands and cays, stretching south to Union Island offering an incredible variety of charter destinations and diversions, in all directions. With gorgeous scenery and secluded beaches, calm anchorages and picturesque villages a Grenadines yacht charter has something for everyone. The Grenadines offer it all, from the bustling waterfront of Port Elizabeth on Saint Vincent, to the stunning natural beauty of the Tobago Cays.

The main group of islands that make up to Saint Vincent and the Grenadines which you can visit on your luxury charter yacht include Young Island (Grenadines), Bequia, Moonhole Rock, Petite Nevis, Quatre, Bettowia, Baliceaux, Mustique, Petite Mustique, Savan, Petite Canouan, Canouan, Mayreau, The Tobago Cays, Union Island, Petit Saint Vincent, Palm Island and Mopion. A few of the islands are inhabited, but many are simply bird sanctuaries and environmental sites.
The Caribbean Island of Barbados is the most easterly island in the Lesser Antilles Caribbean chain of islands. Friendly and relaxed, Barbados is a relatively flat tropical Caribbean island with an abundant supply of large gradually sloping beaches punctuated by sandstone cliffs. Barbados is home to Mount Gay Rum and holds many festivals and sailing events every year. Barbados offers a great nightlife, shops and restaurants as well as many beautiful natural landscapes.

Grenada is an island country consisting of the main island of Grenada and six smaller islands and is one of the most beautiful destinations in the West Indies. Grenada is known as the "Island of Spice" or the Spice Islands due its production of aromatic crops grown in its fertile soil. Grenada is a popular yacht charter destination because of its tranquil sea, beautiful climate, excellent sea conditions, and beautiful beaches and provides easy access for charter yachts to the Grenadines.
View yacht charters for Windward Islands
Below is a selection of Windward Islands charter yacht - please contact us for detailed information and presonalised charter itineraries.
Charter Yachts in Windward Islands
Client Testimonials
What our clients say about their charter experience.
Dear Crossed Sabre team, we were VERY happy with the entire experience and very appreciative of all that you, your crew and your chef did to accommodate our religious requirements and to provide our family with a beautiful experience. Captain Simon was the best we have had yet, and we liked our previous captain very much. We liked your calm demeanour, your humility and your genuine desire to make sure we had a great experience. We also appreciated how good you were with the children, including playing chess with them and just in general how you were very easy to speak with. All the crew were excellent and very service-oriented and super respectful. I was especially grateful for the sincere concern all the crew had to be sure our religious needs were fully met, and everyone went above and beyond in this regard, which was very much appreciated. The chef had a calm and easy demeanour and was easy to communicate with, and the meals were excellent. As for my father, it was fantastic that he was able to work out regularly with a crew member. We want to make sure you know how much we appreciated all that you and your team did for us; we were very happy with everything. We know that accommodating strict kosher requirements was not easy, but it was done very well.
They absolutely loved the boat and described it as phenomenal. The meeting with the captain at a café the day before departure was excellent and helped establish a great rapport. They loved the flexibility of having the captain tailor each day around their preferences. The boat would typically move in the morning, although some evenings they would travel as well. The food onboard was exceptional. They did not want to miss a single meal and were consistently impressed with the quality. The crew's service was a major highlight. They loved that the crew knew one another well and were all Croatian, which created a very warm and cohesive atmosphere. The crew offered two massages each day, allowing everyone to take turns enjoying them. The captain would regularly go into town to purchase fresh produce and local fish, which added a wonderful local element to the experience. One day, the captain went out diving for octopus and later enjoyed it as part of their onboard meal. Overall Takeaway: The clients were exceptionally positive about the trip, with the yacht experience, crew, flexibility, food, and personalised service standing out above everything else. They repeatedly emphasised how much they loved being onboard and how little they wanted to leave the boat.
What can we say? Unbelievably amazing experience. You are all such wonderful people whom we can now consider friends we hope to have long into the future. Thank you for sharing your hospitality and incredible country with us; we could not have asked for a better experience. We look forward to seeing you all in the very near future – in Croatia or Florida. All the very best and with much affection
To the Reverie team: We want to say a huge thank you for everything you have done for us on this trip. You are the best crew we have ever had on a yacht, hands down. Everything has been flawless. Keith’s food has been healthy, tasty, voluminous, and so varied. The toys and tenders were always ready for us when we needed them, and we loved having 3 Sea-Bobs, 3 efoils and 2 jet skis. Always charged and ready to go, from the moment we woke until we went to bed. Our rooms were cleaned so fast we often wondered if there were fairies who appeared and did it. Our washing was done and returned so quickly we wondered if we dreamed it. Service was perfect (thanks Megan and team!) - always nearby when we needed it, and invisible when we didn’t. We aren’t sure how we will survive at home, and there won’t be a drink, a cold towel and a smile waiting for us. Shane - you found us the best anchorages - exactly where we wanted to be - out of the way, out of the wind, but close to everything. We wanted adventures, and you went out of your way to source e-bikes, which ended up being a highlight. We know it wasn’t easy to find or to get them on and off the boat. The smaller things: remembering everyone’s names; the printed AllTrails maps; taking our kids jet skiing. They have all been noticed and appreciated. We know that it isn’t easy to build a team that can create such an exceptional experience. Congratulations to everyone on board - including those behind the scenes we don’t get to see as much. We would love to come back again next year - only if the crew is the same! Thanks so much!
Thank you all so much for such an amazing week! We had such a fabulous time thanks to each & everyone of you! Looking forward to seeing you in Dublin.
You guys knocked it out of the park again – we had such a super time! Thanks again to all for looking after us so well and all welcome in Dublin at any time!
