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Secure your yacht in The Windward Islands
Volcanic Peaks, Open Horizons
Luxury Yacht Charters in the Windward Islands
A Windward Islands yacht charter takes you to the greener, wilder south of the Caribbean, where volcanic peaks rise from the sea, and rainforest runs down to quiet bays. Distances between islands are longer than in the northern Caribbean, and the trade winds are steadier, which rewards sailing yachts and guests who enjoy time at sea. From the harbors of Martinique and St Lucia to the reefs of the Grenadines, the region offers nature, privacy, and a slower rhythm, with the best weather from December to April.
Explore our curated collection of luxury yachts and crewed catamarans. Our independent brokers can also introduce you to exclusive yachts beyond the published selection.
SAMURAI
Built 2016
· Refit 2022
60.3 mLength12Guests6Cabins15Crew
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NALANI
Built 2024
23.87 mLength10Guests5Cabins4Crew
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LADY ROSE
Built 2026
20.55 mLength8Guests4Cabins3Crew
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MARIA THERESE
Built 2024
20.57 mLength8Guests4Cabins4Crew
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INDABLUE
Built 2017
· Refit 2023
22.56 mLength7Guests3Cabins4Crew
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REVE BLEU
Built 2023
20.55 mLength8Guests4Cabins4Crew
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LUNA
Built 2018
· Refit 2024
90 mLength12Guests7Cabins30Crew
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PLAN B
Built 2012
73.07 mLength12Guests8Cabins20Crew
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GRAND OCEAN
Built
· Refit 2025
85 mLength24Guests14Cabins28Crew
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+ VAT, APA & expenses
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CHRISTINA O
Built 1943
· Refit 2022
99.13 mLength34Guests17Cabins40Crew
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Q 72
Built 2012
· Refit 2025
72.45 mLength12Guests8Cabins18Crew
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+ VAT, APA & expenses
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QUANTUM OF SOLACE
Built 2012
· Refit 2022
72.6 mLength12Guests7Cabins19Crew
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+ VAT, APA & expenses
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Beyond the collection
The right yacht isn't always listed.
Our independent brokers work across the wider charter market, including yachts that are never publicly advertised. Tell us what you have in mind and we'll put together a selection for you.
CHARTER EXPERTISE
Your First Yacht Charter
A thoughtful introduction to yacht chartering, from choosing the right yacht to life on board.
READ THE GUIDE ↗
DESTINATIONS & EXPERIENCES
Discover Extraordinary Itineraries
Explore remarkable destinations and cruising routes, thoughtfully curated by our charter specialists.
GET INSPIRED ↗
THE destination advantage
Where the Caribbean Turns Green
The Windward Islands are the Caribbean at its most dramatic, with higher mountains, deeper greens, and fewer crowds. Here is what sets them apart:
✔ Greener, more dramatic landscapes
✔ Less crowded cruising grounds
✔ Excellent sailing conditions for longer passages
✔ Rich local culture and authentic island life
✔ Ideal for nature-focused and experience-driven itineraries
✔ Well suited to experienced charter guests
A Windward Islands yacht charter is perfect for those who value scenery, tranquillity and meaningful exploration. It’s ideal for guests who value scenery and calm over nightlife.
Charter Insight: “Give the Windwards a full ten days if you can. Distances are longer than in the northern Caribbean, and the Tobago Cays and Mustique are best visited unhurried, in the morning, when the light is clear. Book Christmas and New Year as early as possible, as the best yachts are reserved many months ahead.” Giulia Di Leo, CEO and MYBA and CYBA broker
CONTACT A BROKER
Five Islands, Five Characters
Each island has its own personality, and a charter usually combines two or three of them. St Lucia and Dominica suit guests who love hiking and rainforest; the Grenadines are the classic sailing grounds with reefs and beach bars; and Martinique and Grenada add French and Spice Island flavors. Choose your preferred pace, and your crew plans the rest.
Contact a Broker
St Lucia
A visually striking island defined by the Pitons, rainforest, and volcanic scenery.
✔ Iconic anchorages beneath the Pitons
✔ Luxury resorts and natural attractions
✔ Excellent hiking, diving, and wellness experiences
St Vincent & the Grenadines
One of the Caribbean’s most celebrated cruising grounds, offering a chain of islands ideal for yacht exploration.
✔ Bequia, Mustique, Canouan and Tobago Cays
✔ Pristine anchorages and turquoise lagoons
✔ Ideal for extended island-hopping itineraries
Grenada
Known as the “Spice Island,” offering varied cruising and a relaxed atmosphere.
✔ Waterfalls, rainforests, and quiet bays
✔ Excellent diving and snorkeling
✔ Gateway to the southern Windward Islands
Martinique
A sophisticated island combining French culture with Caribbean landscapes.
✔ Refined gastronomy and modern marinas
✔ Volcanic scenery and national parks
✔ Excellent provisioning and infrastructure
Dominica
One of the Caribbean’s most untouched islands, ideal for eco-focused charters.
✔ Rainforests, waterfalls, and geothermal features
✔ Minimal development and wild anchorages
✔ Perfect for nature lovers and adventurous itineraries
THE CHARTER JOURNEY
Three Charter Routes Through the Windwards
These three routes show how a Windward charter can take different shapes. The classic Grenadines week runs through Bequia, Mustique, Canouan and the Tobago Cays, and our 7-night itinerary from St Vincent follows it day by day. A longer cruise links Martinique and the Grenadines, as in our two Martinique itineraries, and the 14-day Lesser Antilles itinerary covers a full two weeks along the chain. We can adjust each to your dates, yacht, and season.
YOUR JOURNEY, DAY BY DAY
A Week Through the Grenadines
This week starts in St Vincent, moves south through Bequia, Mustique and Canouan to the Tobago Cays and Union Island, then heads back north. Each day is adapted to the weather and the size of the yacht, and several stops carry notes on marine park rules, private islands and exposed crossings. Treat it as a model: we adjust it to your group, and extensions to St Lucia, Dominica or Grenada are possible.
DAY 1
St Vincent to Bequia
Begin your private yacht charter in St Vincent, where your captain and crew welcome you aboard. Cruise south toward Bequia, a beautiful island with a rich maritime heritage and a relaxed Caribbean atmosphere. Arrive in Admiralty Bay, surrounded by green hills, colourful waterfront buildings and visiting yachts. Spend the afternoon swimming, exploring Port Elizabeth or relaxing aboard before enjoying your first sunset dinner overlooking the bay.
YBH note: Embarkation takes place at the confirmed St Vincent facility. The crossing to Bequia is exposed to the easterly trade winds and can be lively. The captain will select a suitable overnight anchorage and verify current mooring arrangements.
DAY 2
Mustique & Basil's Bar
Cruise south toward Mustique, one of the Caribbean’s most exclusive private-island destinations. Arrive in Britannia Bay, where beautiful turquoise waters and a relaxed yet sophisticated atmosphere create a memorable setting. Spend the afternoon swimming, enjoying the island scenery or arranging a visit ashore. Discover the legendary Basil’s Bar for sunset cocktails before returning aboard for an elegant evening under the Caribbean stars.
YBH note: Mustique is privately managed. Visiting yachts must comply with local mooring arrangements, and shore facilities or private experiences may require reservations. Access to private estates and beaches is not unrestricted.
DAY 3
Canouan's Turquoise Bays
Continue south through the beautiful Grenadines toward Canouan, an island celebrated for its turquoise waters, white-sand beaches and refined resort experiences. Enjoy scenic cruising along the coastline before arriving at a suitable anchorage. Spend the afternoon swimming, enjoying the yacht’s water toys or arranging a private dining experience ashore. Relax aboard as the sun sets over the surrounding islands.
YBH note: Some Canouan beaches and resort facilities are privately managed. Yacht berthing, tender access and restaurant reservations must be arranged in advance. Reef-fringed eastern waters require careful navigation.
DAY 4
The Spectacular Tobago Cays
Discover the Tobago Cays, one of the Caribbean’s most extraordinary natural cruising destinations. This collection of small uninhabited islands is surrounded by brilliant turquoise waters and protected by the magnificent Horseshoe Reef. Enjoy swimming, snorkelling and observing marine life in permitted areas, including the possibility of seeing sea turtles. Spend the afternoon relaxing aboard, surrounded by spectacular island scenery, before a peaceful evening in a suitable designated mooring area.
YBH note: The Tobago Cays are a protected marine park. Entry fees, mooring requirements, no-anchoring zones and restrictions on fishing, diving and water toys may apply. Yacht size and draft determine whether a vessel can safely enter or remain in the lagoon.
DAY 5
Mayreau & Union Island
Cruise toward Mayreau, a beautiful small island known for its relaxed atmosphere and the picturesque crescent of Salt Whistle Bay. Enjoy scenic cruising, swimming and a leisurely lunch aboard before continuing toward Union Island. Discover the colourful waterfront around Clifton and admire the dramatic volcanic hills that rise above the surrounding turquoise waters. Enjoy a relaxed evening aboard or a casual Caribbean dining experience ashore.
YBH note: Salt Whistle Bay is small and can be crowded, with limited room for larger yachts. Union Island's shallow reef approaches require careful navigation. Shore facilities and services should be reconfirmed following the significant hurricane damage experienced in 2024.
DAY 6
Cruising North Through the Grenadines
Enjoy a beautiful northbound passage through the Grenadines, admiring the remarkable island scenery that makes this region so rewarding to explore by private yacht. Depending on weather and timing, pause near Canouan for a final swim before continuing toward Bequia. Arrive in Admiralty Bay for a relaxed final evening, enjoying sunset views, waterfront dining or a special farewell dinner prepared by your private chef.
YBH note: This is the itinerary's longest scheduled cruising day, with a substantial northbound passage against prevailing trade-wind conditions. For a slower-paced charter, consider a one-way itinerary ending farther south or arrange a different embarkation point.
DAY 7
Return to St Vincent
Enjoy your final morning aboard while cruising north toward St Vincent. Admire the island’s dramatic green coastline and beautiful Caribbean scenery before returning to the confirmed disembarkation location. Conclude your seven-day Windward Islands yacht charter with unforgettable memories of Mustique, Canouan, the Tobago Cays and the remarkable natural beauty of the Grenadines.
YBH note: The return must follow the charter agreement and confirmed disembarkation arrangements. For early morning departures, the yacht should normally return to St Vincent on Day 6.
DISCOVER ALONG THE WAY
Peaks, Bays and Marine Parks
These eight places shape most Windward charters, from the Pitons and Admiralty Bay to the protected waters of the Tobago Cays. Some are marine parks with fees and no-anchor zones, some are privately managed and some have limited space, so your captain confirms access ahead of time.
Landmark
Southwestern St Lucia
The Pitons & Soufrière Bay
Discover the magnificent Pitons of St Lucia, where two extraordinary volcanic peaks rise dramatically above the Caribbean coastline. Cruising beneath these UNESCO-listed landmarks offers one of the most memorable experiences in the Windward Islands. The surrounding marine management area includes designated yacht moorings, beautiful snorkelling opportunities and access to luxury resorts and waterfront experiences near Soufrière. Mooring arrangements must follow local marine management regulations.
Port
Port Elizabeth · Bequia
Admiralty Bay
Discover Admiralty Bay, the maritime heart of Bequia and one of the Grenadines’ most welcoming yacht destinations. Surrounded by lush hillsides and the charming waterfront of Port Elizabeth, the bay offers a beautiful setting for relaxed cruising, swimming and dining ashore. Its longstanding yachting tradition and distinctive island atmosphere make Bequia an essential stop on a Windward Islands charter.
Port
Mustique · The Grenadines
Britannia Bay & Basil's Bar
Arrive in Britannia Bay on Mustique, a celebrated private island known for its beautiful natural scenery and understated luxury. Visiting yachts can enjoy the island’s relaxed waterfront atmosphere, with Basil’s Bar providing a memorable setting for lunch, cocktails or an evening ashore. The surrounding waters offer beautiful views of the Grenadines, while yacht moorings and shore activities remain subject to local arrangements and private-island policies.
Protected Area
Southern Grenadines · St Vincent and the Grenadines
Tobago Cays Marine Park
Explore the Tobago Cays, one of the Caribbean’s most beautiful marine environments, where five small uninhabited islands sit within brilliant turquoise waters protected by Horseshoe Reef. Enjoy swimming, snorkelling and observing marine life in authorised areas, with unforgettable views of the surrounding islands. The marine park is environmentally sensitive, and all yacht activities must comply with its regulations, designated moorings and applicable fees.
Beach
Canouan · The Grenadines
Canouan & Charlestown Bay
Discover Canouan, a beautiful island surrounded by clear Caribbean waters and spectacular coastal scenery. Known for its exclusive resorts, white-sand beaches and refined atmosphere, Canouan offers an appealing contrast to the more traditional island villages of the Grenadines. Visiting yachts can enjoy scenic cruising, swimming and carefully arranged waterfront dining or resort experiences, subject to local access and berthing arrangements.
Beach
Mayreau · The Grenadines
Salt Whistle Bay
Discover Salt Whistle Bay, one of the Grenadines’ most recognisable coastal landscapes, where a graceful curve of white sand meets turquoise Caribbean water. The surrounding palm trees and low green hills create an idyllic setting for swimming and relaxing aboard. The bay is relatively small and popular with visiting yachts, so anchoring space, weather exposure and vessel dimensions must be considered carefully.
Port
Portsmouth · Northern Dominica
Prince Rupert Bay
Discover Prince Rupert Bay on Dominica’s northwestern coastline, where lush tropical hills rise above a beautiful natural harbour. Portsmouth provides a memorable gateway to Dominica’s remarkable rainforest landscapes, river excursions and distinctive Caribbean culture. Visiting yachts can arrange local guides and authorised mooring services, with the bay offering an appealing stop on longer Windward Islands itineraries.
Beach
Southwestern Grenada
Grand Anse Beach
Discover Grand Anse, one of Grenada’s most celebrated beaches, where a long stretch of pale sand meets beautiful Caribbean waters. The surrounding coastline offers attractive opportunities for scenic cruising, swimming and relaxed beachside experiences. Grenada also provides established yacht facilities near St George’s, making it an appealing embarkation or disembarkation destination for extended Windward Islands charters.
destination insights
The Details That Make the Difference
Expert perspectives and practical guidance for planning your yacht charter.
Choosing Your Months
The best time for a Windward Islands yacht charter is generally December through April, when warm Caribbean temperatures, lower rainfall, and established northeast trade winds create attractive conditions for exploring St Lucia, St Vincent and the Grenadines, and Grenada. February, March and April are especially appealing for island-hopping between Bequia, Mustique, Canouan and the Tobago Cays. Trade winds can create lively passages between islands, even during the dry season, making thoughtful route planning essential. The Atlantic hurricane season extends from June through November, with the highest historical tropical cyclone activity typically occurring between August and October. Your Boat Holiday designs every itinerary around seasonal conditions, yacht capabilities, and guest preferences.
✔ December – April: Peak season with stable weather
✔ January – March: Ideal for longer sailing itineraries
✔ April: Warm seas and quieter anchorages
✔ May – August: Select availability depending on yacht and routing
✔ September – October: Low season due to hurricane risk
Windward itineraries are often planned for longer durations due to cruising distances.
January
Excellent
24–29°C
Air
27°C
Sea
8 h
Sunshine
16 kn
Wind
YBH note: A prime yacht charter month, with warm tropical temperatures and generally favourable dry-season conditions. Fresh northeast trade winds can create energetic sailing and choppy inter-island passages.
Days of Rainforest and Reef
Days in the Windwards balance time on the water with walks ashore and snorkeling. A typical stop includes:
✔ Hike to a waterfall or a volcanic viewpoint
✔ Snorkel a protected reef or swim with turtles
✔ Anchor in a quiet bay far from the main harbor
✔ Lunch at a beach bar in Bequia or Mustique
✔ Sail between islands in steady trade winds
The Windward Islands deliver a deeper, more authentic Caribbean experience.
Choose My Pace
Which Yacht for the Windwards?
The Windwards reward yachts that love to sail, and this first selection shows the range. Looma and Adeona are two Fountaine Pajot Alegria 67 sailing catamarans for eight guests: Looma is built for water sports, with a skurf, electric surf and sea scooters, while Adeona adds a deck jacuzzi, an eFoil, and Seabobs for the Grenadines reefs. For a quieter way to cover the distances, Double Happiness is an eco-focused Sunreef 60 power catamaran, with a flybridge barbecue, a hydraulic swim platform and electric bikes for exploring ashore.
At the larger end, Mes Amis is a 44-meter Fitzroy sailing yacht designed by Dubois, with an oak-and-walnut interior, World Superyacht Awards recognition, and a 15-meter tender for days ashore. For guests who prefer speed and space on longer passages between islands, we offer a carefully selected range of hand-picked motor yachts and superyachts suited to the Windwards.
Tell us your dates and group, and we will confirm availability and look beyond this list if you prefer.
Ask About These
THE GUEST BOOK
Moments We Helped Create
Guests share what their charter meant to them.
"I will remember this charter for the rest of my life... I proposed to my now fiancée in the Tobago Cays, surrounded by the most beautiful water I've ever seen. I was so nervous, but everything turned out even better than I imagined. The crew helped me keep it all a surprise and made that moment so special for both of us. The Grenadines will always have a very special place in our hearts. Thank you for helping me make this happen!!"George S.Guest aboard 42m motor yacht, 7-night charter from/to
Questions & Answers
Answers for Windward Yachting
Answers to what guests ask most before chartering in the Windward Islands.
PRIVATE YACHT CHARTER ADVISORY
The right yacht changes everything. The right people make it yours.
Independent yacht selection, firsthand knowledge and personal assistance — from your first enquiry to your return home.
Your journey, our expertise.
Independent selection. Explore publicly listed and off-market yachts through our international brokerage network, without fleet bias.
Firsthand knowledge. We inspect yachts, meet crews and help tailor every detail to your cruising plans.
Professional credentials. Our team is active in established yacht brokerage associations, including MYBA, IYBA and CYBA.
Planning a yacht charter in The Windward Islands? Tell us your preferred dates, guests and expectations — our brokers will prepare a considered proposal.
Request Your Private Yacht Proposal
Share a few details about your plans. A YBH charter broker will personally review your request and recommend suitable yachts.
