The Ultimate 7-Night Luxury Sailing Adventure Through the Windward Islands
Volcanoes, Trade Winds, and the Most Varied Sailing Week in the Caribbean
Some Caribbean routes feel like a holiday.
This one feels like movement - a steady unfolding of landscapes, cultures, and anchorages that change character every single day.
This is not a static itinerary. It’s a sequence of contrasts.
This one feels like movement - a steady unfolding of landscapes, cultures, and anchorages that change character every single day.
This is not a static itinerary. It’s a sequence of contrasts.
THIS IS NOT A STATIC ITINERARY. IT'S A SEQUENCE OF CONTRASTS
The Windward Islands sit in a rare sweet spot for sailing: close enough for short, comfortable passages, yet diverse enough to feel like multiple countries stitched into one voyage. French bakeries in Martinique, towering volcanic ridges in Saint Lucia, raw coastal villages in Saint Vincent, and the almost surreal beauty of the Grenadines all sit within a week’s reach.
Designed for fully crewed luxury sailing catamarans between 50 and 60 feet, the route balances easy daily passages, protected anchorages, world-class snorkeling, and the kind of quiet evenings at anchor that define a proper Caribbean voyage.
The loop begins and ends in Le Marin, Martinique, tracing a natural arc south through Saint Lucia and the Grenadines, before turning back north via Canouan and the Saint Lucia channel.
The Windward Islands sit in a rare sweet spot for sailing: close enough for short, comfortable passages, yet diverse enough to feel like multiple countries stitched into one voyage. French bakeries in Martinique, towering volcanic ridges in Saint Lucia, raw coastal villages in Saint Vincent, and the almost surreal beauty of the Grenadines all sit within a week’s reach.
Designed for fully crewed luxury sailing catamarans between 50 and 60 feet, the route balances easy daily passages, protected anchorages, world-class snorkeling, and the kind of quiet evenings at anchor that define a proper Caribbean voyage.
The loop begins and ends in Le Marin, Martinique, tracing a natural arc south through Saint Lucia and the Grenadines, before turning back north via Canouan and the Saint Lucia channel.
Le Marin, Martinique → Rodney Bay, Saint Lucia → Marigot Bay → Soufrière → Wallilabou Bay, Saint Vincent → Bequia → Mustique → Tobago Cays → Canouan → Le Marin, Martinique
RECOMMENDED 7-NIGHT LUXURY SAILING ITINERARY THROUGH THE WINDWARD ISLANDS
Day 1: Le Marin, Martinique → Rodney Bay, Saint Lucia
Distance: 22 NM
Sailing Time: 3.5 Hours
Martinique
Martinique sets a tone that is immediately different from most Caribbean islands.
It feels structured, refined, and unmistakably French — bakeries, wine shops, marina cafés, and an almost European sense of order layered onto a tropical coastline.
Saint Lucia
Saint Lucia is the first real shift in scenery.
The island rises abruptly from the sea, dense with rainforest and carved by steep valleys. You don’t approach it gradually — you notice it long before you arrive.
What to Do
• Settle into Rodney Bay Marina
• Easy first swim off the yacht
• Sunset dinner ashore
• Walk the marina village
Overnight
Marina: Rodney Bay Marina
Why:
• Excellent protection
• Full provisioning options
• Smooth first-night anchorage
• Comfortable reset after embarkation
Distance: 22 NM
Sailing Time: 3.5 Hours
Martinique
Martinique sets a tone that is immediately different from most Caribbean islands.
It feels structured, refined, and unmistakably French — bakeries, wine shops, marina cafés, and an almost European sense of order layered onto a tropical coastline.
Saint Lucia
Saint Lucia is the first real shift in scenery.
The island rises abruptly from the sea, dense with rainforest and carved by steep valleys. You don’t approach it gradually — you notice it long before you arrive.
What to Do
• Settle into Rodney Bay Marina
• Easy first swim off the yacht
• Sunset dinner ashore
• Walk the marina village
Overnight
Marina: Rodney Bay Marina
Why:
• Excellent protection
• Full provisioning options
• Smooth first-night anchorage
• Comfortable reset after embarkation
Day 2: Saint Lucia: Rodney Bay → Marigot Bay → Soufrière
Distance: 18 NM
Sailing Time: 3 Hours
Saint Lucia in Full Contrast
This is the day Saint Lucia reveals its depth.
Marigot Bay feels enclosed and cinematic - steep green hills wrapping around a quiet harbor. Further south, the coastline becomes more dramatic until the Pitons appear, rising like geological monuments straight from the sea.
What to Do
• Cruise Marigot Bay
• Swim beneath the Pitons
• Visit Sulphur Springs
• Explore Soufrière village
• Snorkel volcanic coastline
Special Highlights
The Pitons are not just scenic landmarks - they define the island’s identity. Approaching them under sail is one of those moments guests tend to remember more clearly than expected.
Overnight
Anchorage: Soufrière Bay
Why:
• Exceptional scenery
• Protected waters
• Easy access to shore experiences
• Strong snorkeling conditions
Distance: 18 NM
Sailing Time: 3 Hours
Saint Lucia in Full Contrast
This is the day Saint Lucia reveals its depth.
Marigot Bay feels enclosed and cinematic - steep green hills wrapping around a quiet harbor. Further south, the coastline becomes more dramatic until the Pitons appear, rising like geological monuments straight from the sea.
What to Do
• Cruise Marigot Bay
• Swim beneath the Pitons
• Visit Sulphur Springs
• Explore Soufrière village
• Snorkel volcanic coastline
Special Highlights
The Pitons are not just scenic landmarks - they define the island’s identity. Approaching them under sail is one of those moments guests tend to remember more clearly than expected.
Overnight
Anchorage: Soufrière Bay
Why:
• Exceptional scenery
• Protected waters
• Easy access to shore experiences
• Strong snorkeling conditions
Day 3: Saint Lucia, Soufrière → Wallilabou Bay, Saint Vincent
Distance: 28 NM
Sailing Time: 4.5 Hours
Saint Vincent
Saint Vincent feels less curated than its neighbors. That’s its strength. This is a working island - fishing villages, rugged coastline, and landscapes that haven’t been softened for tourism. It feels authentic in a way that is increasingly rare in the Caribbean.
What to Do
• Visit Wallilabou Bay (film location of Pirates of the Caribbean)
• Explore black-sand beaches
• Walk through small coastal villages
• Enjoy local food ashore
Special Highlights
Wallilabou Bay has a slightly cinematic quality — not polished, but atmospheric. It carries a sense of maritime history and lived-in coastal life.
Overnight
Anchorage: Wallilabou Bay
Why:
• Good natural shelter
• Character-rich setting
• Quiet overnight conditions
Distance: 28 NM
Sailing Time: 4.5 Hours
Saint Vincent
Saint Vincent feels less curated than its neighbors. That’s its strength. This is a working island - fishing villages, rugged coastline, and landscapes that haven’t been softened for tourism. It feels authentic in a way that is increasingly rare in the Caribbean.
What to Do
• Visit Wallilabou Bay (film location of Pirates of the Caribbean)
• Explore black-sand beaches
• Walk through small coastal villages
• Enjoy local food ashore
Special Highlights
Wallilabou Bay has a slightly cinematic quality — not polished, but atmospheric. It carries a sense of maritime history and lived-in coastal life.
Overnight
Anchorage: Wallilabou Bay
Why:
• Good natural shelter
• Character-rich setting
• Quiet overnight conditions
Day 4: Saint Vincent → Bequia
Distance: 10 NM
Sailing Time: 1.5 Hours
Bequia
Bequia is where the Windward Islands soften. The harbor fills with small fishing boats, wooden dinghies, and sailboats that seem to move at their own pace. Everything here feels human-scaled and unhurried.
What to Do
• Walk Port Elizabeth
• Visit local boat builders
• Swim Princess Margaret Beach
• Explore Belmont Walkway
Special Highlights
Bequia is often described by experienced sailors as the island that feels the most “livable” in the entire Grenadines chain.
Overnight
Anchorage: Admiralty Bay
Why:
• Excellent holding
• Strong shelter
• Easy shore access
• Relaxed evening atmosphere
Distance: 10 NM
Sailing Time: 1.5 Hours
Bequia
Bequia is where the Windward Islands soften. The harbor fills with small fishing boats, wooden dinghies, and sailboats that seem to move at their own pace. Everything here feels human-scaled and unhurried.
What to Do
• Walk Port Elizabeth
• Visit local boat builders
• Swim Princess Margaret Beach
• Explore Belmont Walkway
Special Highlights
Bequia is often described by experienced sailors as the island that feels the most “livable” in the entire Grenadines chain.
Overnight
Anchorage: Admiralty Bay
Why:
• Excellent holding
• Strong shelter
• Easy shore access
• Relaxed evening atmosphere
Day 5: Bequia → Mustique → Tobago Cays
Distance: 30 NM
Sailing Time: 5 Hours
Mustique
Mustique is subtle rather than loud. Private villas hidden behind vegetation, quiet beaches, and an atmosphere of controlled exclusivity define the island. Even a short stop feels distinct.
Tobago Cays
And then the shift is absolute. The sea opens into a protected lagoon of impossible colors. Water clarity increases until depth becomes visually irrelevant. Sea turtles appear without effort or expectation.
What to Do
• Swim with sea turtles
• Snorkel Horseshoe Reef
• Paddleboard in shallow lagoons
• Beach barbecue on deserted islets
• Sunset cocktails on board
Special Highlights
Tobago Cays is one of the few places in the Caribbean where reality consistently underperforms memory - even while you are still there.
Overnight
Mooring: Tobago Cays Marine Park
Why:
• Fully protected waters
• Extraordinary marine life
• No light pollution
• One of the Caribbean’s most iconic anchorages
Distance: 30 NM
Sailing Time: 5 Hours
Mustique
Mustique is subtle rather than loud. Private villas hidden behind vegetation, quiet beaches, and an atmosphere of controlled exclusivity define the island. Even a short stop feels distinct.
Tobago Cays
And then the shift is absolute. The sea opens into a protected lagoon of impossible colors. Water clarity increases until depth becomes visually irrelevant. Sea turtles appear without effort or expectation.
What to Do
• Swim with sea turtles
• Snorkel Horseshoe Reef
• Paddleboard in shallow lagoons
• Beach barbecue on deserted islets
• Sunset cocktails on board
Special Highlights
Tobago Cays is one of the few places in the Caribbean where reality consistently underperforms memory - even while you are still there.
Overnight
Mooring: Tobago Cays Marine Park
Why:
• Fully protected waters
• Extraordinary marine life
• No light pollution
• One of the Caribbean’s most iconic anchorages
Day 6: Tobago Cays → Mayreau
Distance: 4 NM
Sailing Time: Less Than 1 Hour
Why Mayreau?
Mayreau is the smallest inhabited island in the Grenadines and one of the easiest places in the Caribbean to fall in love with. With a population of only a few hundred residents, there are no large resorts, no cruise terminals, and no busy roads. Life moves at a completely different pace here. Colorful homes cling to green hillsides above turquoise bays. Small beach bars serve fresh lobster and cold rum punch. Sailboats gently swing at anchor just offshore.
For many guests, Mayreau feels like the Caribbean they imagined before mass tourism arrived.
What to Do
• Swim in Salt Whistle Bay
• Walk to the hilltop church
• Explore the island village
• Enjoy lunch at a local beach restaurant
• Watch sunset from the western shore
Special Highlights
The viewpoint beside the Catholic church offers one of the most spectacular panoramas anywhere in the Caribbean. From here, the entire Tobago Cays Marine Park unfolds below you, framed by reefs, lagoons, and distant islands. Many photographers consider it one of the finest viewpoints in the Eastern Caribbean.
Overnight
Anchorage: Salt Whistle Bay
Why:
• One of the most iconic anchorages in the Caribbean
• Crystal-clear water
• Excellent swimming
• Palm-lined beach
• Beautiful sunset views
Distance: 4 NM
Sailing Time: Less Than 1 Hour
Why Mayreau?
Mayreau is the smallest inhabited island in the Grenadines and one of the easiest places in the Caribbean to fall in love with. With a population of only a few hundred residents, there are no large resorts, no cruise terminals, and no busy roads. Life moves at a completely different pace here. Colorful homes cling to green hillsides above turquoise bays. Small beach bars serve fresh lobster and cold rum punch. Sailboats gently swing at anchor just offshore.
For many guests, Mayreau feels like the Caribbean they imagined before mass tourism arrived.
What to Do
• Swim in Salt Whistle Bay
• Walk to the hilltop church
• Explore the island village
• Enjoy lunch at a local beach restaurant
• Watch sunset from the western shore
Special Highlights
The viewpoint beside the Catholic church offers one of the most spectacular panoramas anywhere in the Caribbean. From here, the entire Tobago Cays Marine Park unfolds below you, framed by reefs, lagoons, and distant islands. Many photographers consider it one of the finest viewpoints in the Eastern Caribbean.
Overnight
Anchorage: Salt Whistle Bay
Why:
• One of the most iconic anchorages in the Caribbean
• Crystal-clear water
• Excellent swimming
• Palm-lined beach
• Beautiful sunset views
Day 7: Mayreau → Canouan
Distance: 15 NM
Sailing Time: 2.5 Hours
Why Canouan?
Canouan introduces a different side of the Grenadines. While neighboring islands are known for their simplicity and laid-back atmosphere, Canouan blends natural beauty with a level of luxury rarely found elsewhere in the region. The island's spectacular marina attracts superyachts from around the world while remaining remarkably uncrowded.
What to Do
• Visit Sandy Lane Yacht Club
• Enjoy a luxury beach club lunch
• Explore Godahl Beach
• Watersports from the yacht
• Sunset cocktails overlooking the marina
Special Highlights
Canouan has quietly become one of the Eastern Caribbean's premier luxury yachting destinations. The marina regularly welcomes vessels worth tens and sometimes hundreds of millions of dollars.
Overnight
Marina: Sandy Lane Yacht Club
Why:
• World-class facilities
• Luxury dining
• Excellent protection
• Ideal location before returning north
Distance: 15 NM
Sailing Time: 2.5 Hours
Why Canouan?
Canouan introduces a different side of the Grenadines. While neighboring islands are known for their simplicity and laid-back atmosphere, Canouan blends natural beauty with a level of luxury rarely found elsewhere in the region. The island's spectacular marina attracts superyachts from around the world while remaining remarkably uncrowded.
What to Do
• Visit Sandy Lane Yacht Club
• Enjoy a luxury beach club lunch
• Explore Godahl Beach
• Watersports from the yacht
• Sunset cocktails overlooking the marina
Special Highlights
Canouan has quietly become one of the Eastern Caribbean's premier luxury yachting destinations. The marina regularly welcomes vessels worth tens and sometimes hundreds of millions of dollars.
Overnight
Marina: Sandy Lane Yacht Club
Why:
• World-class facilities
• Luxury dining
• Excellent protection
• Ideal location before returning north
Day 8: Canouan → Le Marin, Martinique
Distance: 42 NM
Sailing Time: 6.5–7 Hours
An early departure provides a beautiful final sail through the Windward Islands. Flying fish, dolphins, and long ocean views frequently accompany guests on this final passage. As Martinique gradually appears on the horizon, the voyage comes full circle.
Arrival in Le Marin is typically during the afternoon, allowing plenty of time for a relaxed disembarkation the following morning.
Distance: 42 NM
Sailing Time: 6.5–7 Hours
An early departure provides a beautiful final sail through the Windward Islands. Flying fish, dolphins, and long ocean views frequently accompany guests on this final passage. As Martinique gradually appears on the horizon, the voyage comes full circle.
Arrival in Le Marin is typically during the afternoon, allowing plenty of time for a relaxed disembarkation the following morning.
Total Voyage Statistics
Total Distance: 169 Nautical Miles
This itinerary works because it doesn’t try to do everything - it focuses on contrast.
Few sailing regions in the Caribbean compress this level of diversity into a single week without long, exhausting passages. This is why experienced captains often describe the Windward Islands not as one destination, but as several different Caribbean worlds connected by short stretches of blue water.
Day | Route | Distance |
1 | Martinique → Saint Lucia | 22 NM |
2 | Saint Lucia Exploration | 18 NM |
3 | Saint Lucia → Saint Vincent | 28 NM |
4 | Saint Vincent → Bequia | 10 NM |
5 | Bequia → Mustique → Tobago Cays | 30 NM |
6 | Tobago Cays → Mayreau | 4 NM |
7 | Mayreau → Canouan | 15 NM |
8 | Canouan → Martinique | 42 NM |
Total Distance: 169 Nautical Miles
This itinerary works because it doesn’t try to do everything - it focuses on contrast.
- French sophistication in Martinique.
- Volcanic drama in Saint Lucia.
- Authentic island life in Saint Vincent.
- Timeless Caribbean charm in Bequia.
- Private-island exclusivity in Mustique.
- One of the most beautiful marine parks in the world in Tobago Cays.
- And a final touch of understated luxury in Canouan.
Few sailing regions in the Caribbean compress this level of diversity into a single week without long, exhausting passages. This is why experienced captains often describe the Windward Islands not as one destination, but as several different Caribbean worlds connected by short stretches of blue water.
Let’s Start Planning Your Windward Islands Charter
Every voyage we design is tailored around the guests on board - pace, style, dining, activity level, and level of privacy.
Whether your ideal week includes quiet anchorages, beach clubs, snorkeling with turtles, or simply long afternoons on deck with nothing but trade winds and open water, we will shape the itinerary around you.
Contact Emerald Sail, and let’s design your Windward Islands sailing experience.
Oleg Drizen, RYA and IYT Yacht Master Offshore and Ocean, Skipper
Every voyage we design is tailored around the guests on board - pace, style, dining, activity level, and level of privacy.
Whether your ideal week includes quiet anchorages, beach clubs, snorkeling with turtles, or simply long afternoons on deck with nothing but trade winds and open water, we will shape the itinerary around you.
Contact Emerald Sail, and let’s design your Windward Islands sailing experience.
Oleg Drizen, RYA and IYT Yacht Master Offshore and Ocean, Skipper
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