Windward Islands
Windward Islands Yacht Charter Guide
Sweet scents of cinnamon and nutmeg drift on balmy Caribbean breezes, snow-white beaches fringed with palm trees lookout to incredible seas, volcanic hills shrouded in rainforest rise from the sea…the Windward Islands are a paradise on Earth. On these tropical islands, time slows down, so take the opportunity to relax – and there is no better way to do that than on a Windwards Islands yacht charter vacation, cruising around the breathtaking archipelago. Explore deserted beaches, jump into crystalline waters full of marine life and partake in the local pastime – sunbathing on the beach with a coconut in hand!
Best Time To Visit:
The Caribbean is warm all year round, but December to May guarantee dry weather and a chance to top up your winter tan.
Key Cruising Areas:
The seven islets of the archipelago offer plenty of beautiful cruising grounds, stunning beaches, and excellent dive spots to anchor. They are also ideally situated to visit Trinidad and Tobago, or even Cuba sailing north.
Don’t Miss:
A vacation in the Caribbean wouldn’t be complete without sampling the famous rum cocktails. The spirit is an important part of the area’s history, so for a taste of the real Caribbean take a tour of a rum distillery. In River Antoine Estate you can see an authentic distillery and try a rum punch mixed with sorrel.
Best Spots for Wining and Dining:
The proclaimed “best” island in the Grenadines, Bequia is a beautiful location filled with fine dining options. Start with a cocktail at the Open Deck Bar & Restaurant before a five or six-course feast of local fare for an amazing dining experience.
Best Local Dish:
Unsurprisingly, the restaurants of the Caribbean are brimming with delicious, fresh seafood. The Barbadian national food is flying fish, and you may be surprised by how sweet and tender the fish is. True locals take a fried flying fish sandwich to eat on the marina, but for a pretty candlelit meal head to Café Luna at sunset and try their take on the specialty.
Local Culture:
The history of Bridgetown in Barbados is so important to the island that it has become a UNESCO world heritage site. For a great introduction to the culture of the town take a Bajan walking food tour around downtown, where you will learn about the history that shaped the island and taste some local specialties.
Best Beach:
The rather romantically named Pink Gin Beach on Grenada is primarily accessible by boat, giving it a feel of privacy and seclusion. The light sand and shallow, sheltered waters are very safe for swimming, and the views out to the aquamarine waters are stunning.
IYC recommends:
Sail to St Lucia to enjoy the exclusive and stylish Anse Chastanet resort. As well as the 600 tropical acres, the resort’s beach alone is worth the trip – set between incredible, twin volcanic hills, the thatched umbrellas of the beach are nestled into the forest looking out onto surreal white sands. In the evening, dine at the Treehouse Restaurant.
More To Explore
Secluded anchorages, turquoise waters, and unspoiled, authentic islands are the hallmarks of St Vincent and the Grenadines. This group of 32 volcanic islands, located in the southern, windward islands of the Caribbean, has rightfully been gaining increasing momentum as a top-tier destination for a luxury yacht charter.Compared to many other Caribbean hotspots, such as St. Barth or the BVI, St. Vincent and the Grenadines are still relatively undiscovered and less visited. With the 2025 Caribbean yacht charter season upon us, the best time to visit these islands is now, between November and April, when the islands have steady winds and calm seas. Offering an authentic experience of the 'true Caribbean', here is our insider guide to cruising this idyllic region:
The Caribbean is one of the most renowned must-visit yacht-cruising grounds during winter, with classic haunts drawing luxury yachts in to explore. Whether it be the glamorous parties in St Barths, sailing regattas in Antigua, island-hopping itineraries of the BVIs, or the famous swimming pigs in the Bahamas, there is much to offer. And, while these headliner islands typically dominate the yacht charter landscape, the Caribbean has lots more islands to experience that you may not have come across yet.Beyond the frequently visited routes and itineraries lie islands that still offer Caribbean charm but with fewer crowds and a more authentic experience. For the upcoming winter Caribbean yachting season, why not switch out, or even add to, the traditional destination itineraries for one of these alternative islands?Here we have included our favorite lesser-visited Caribbean islands that you should consider adding to your list for your next luxury yacht charter:
The Caribbean is one of the most sought-after locations for a luxury vacation and yacht charter itinerary. Sun-drenched days on endless white sandy beaches, time spent in luxurious resorts, and proximity to island hops on a yacht add to the island's allure, but there is much more to uncover beyond the postcard-perfect scenes.The islands' rich cultural heritage and natural beauty offer various opportunities for discovery, both on and off the beaten track, while the vibrant local traditions, cuisines, and festivals add to the authentic experiences found here. Here, we have put together a guide to some of the more popular Caribbean islands' best-kept secrets: