Saint Martin, Anguilla & St. Barts Sailing Guide
Leeward Islands: The Ultimate 7-Night Luxury Sailing Adventure Through Saint Martin, Anguilla & St. Barts
Where Caribbean Sailing Meets French Elegance.
Some Caribbean destinations are all about remote anchorages. Others are about beaches. A few are known for great sailing.
But there is only one place in the Caribbean where world-class restaurants, chic beach clubs, crystal-clear anchorages, European sophistication, and spectacular sailing all come together in a single week.
That place is the northeastern corner of the Leeward Islands.
Some Caribbean destinations are all about remote anchorages. Others are about beaches. A few are known for great sailing.
But there is only one place in the Caribbean where world-class restaurants, chic beach clubs, crystal-clear anchorages, European sophistication, and spectacular sailing all come together in a single week.
That place is the northeastern corner of the Leeward Islands.
THE FINEST CRUISING GROUNDS IN THE LEEWARD ISLANDS
For guests stepping aboard a luxury sailing catamaran for the first time, this region often exceeds expectations. The distances are short, the scenery changes constantly, and every island has a completely different personality.
Saint Martin delivers an irresistible blend of French culture and Caribbean energy. Anguilla offers some of the finest beaches and clearest water anywhere in the region. St. Barts brings a level of elegance, style, and luxury that has made it one of the most sought-after destinations in the world.
What makes this itinerary so special is its rhythm.
Unlike many Caribbean routes that require long passages between islands, this voyage allows guests to spend less time underway and more time enjoying what they came for in the first place: swimming in turquoise water, discovering hidden beaches, dining ashore, exploring charming waterfront towns, and relaxing aboard a fully crewed luxury catamaran.
Designed specifically for all-inclusive sailing catamarans between 50 and 60 feet, this itinerary combines exceptional anchorages, short and comfortable sailing days, outstanding dining opportunities, and some of the most beautiful water in the Caribbean.
The route begins and ends in Saint Martin and explores the highlights of the region, including glamorous St. Barts, pristine Anguilla, secluded Tintamarre, charming Pinel Island, and several anchorages that remain favorites among experienced captains year after year.
If the Grenadines are about adventure and natural beauty, Saint Martin, Anguilla, and St. Barts are about enjoying the Caribbean at its most polished, relaxed, and effortlessly elegant.
For guests stepping aboard a luxury sailing catamaran for the first time, this region often exceeds expectations. The distances are short, the scenery changes constantly, and every island has a completely different personality.
Saint Martin delivers an irresistible blend of French culture and Caribbean energy. Anguilla offers some of the finest beaches and clearest water anywhere in the region. St. Barts brings a level of elegance, style, and luxury that has made it one of the most sought-after destinations in the world.
What makes this itinerary so special is its rhythm.
Unlike many Caribbean routes that require long passages between islands, this voyage allows guests to spend less time underway and more time enjoying what they came for in the first place: swimming in turquoise water, discovering hidden beaches, dining ashore, exploring charming waterfront towns, and relaxing aboard a fully crewed luxury catamaran.
Designed specifically for all-inclusive sailing catamarans between 50 and 60 feet, this itinerary combines exceptional anchorages, short and comfortable sailing days, outstanding dining opportunities, and some of the most beautiful water in the Caribbean.
The route begins and ends in Saint Martin and explores the highlights of the region, including glamorous St. Barts, pristine Anguilla, secluded Tintamarre, charming Pinel Island, and several anchorages that remain favorites among experienced captains year after year.
If the Grenadines are about adventure and natural beauty, Saint Martin, Anguilla, and St. Barts are about enjoying the Caribbean at its most polished, relaxed, and effortlessly elegant.
Saint Martin, Marigot Bay → Tintamarre → Pinel Island → Anguilla → Prickly Pear Cays → St. Barts → Saint Martin, Simpson Bay
RECOMMENDED 7-NIGHT ST. VINCENT AND THE GRENADINES SAILING ITINERARY
Day 1: Blue Lagoon (St. Vincent) → Bequia
Distance: 9 NM
Sailing Time: 1.5 Hours
Why Bequia?
Bequia is the soul of the Grenadines.
Unlike many Caribbean islands that have become heavily commercialized, Bequia remains charming, relaxed, and genuinely Caribbean. Admiralty Bay is lined with waterfront restaurants, colorful local fishing boats, boutique shops, and friendly locals.
What to Do
• Walk the Belmont Walkway
• Visit the famous model boat builders
• Explore Port Elizabeth
• Enjoy cocktails at Jack's Beach Bar
• Watch sunset from Princess Margaret Beach
Special Highlights
Princess Margaret Beach is widely considered one of the most beautiful beaches in the Grenadines. Crystal-clear water and powder-soft sand make it the perfect introduction to the week ahead.
Overnight
Anchorage: Admiralty Bay
Why:
• Excellent holding
• Well protected
• Close to restaurants and town
• Beautiful nighttime atmosphere
Distance: 9 NM
Sailing Time: 1.5 Hours
Why Bequia?
Bequia is the soul of the Grenadines.
Unlike many Caribbean islands that have become heavily commercialized, Bequia remains charming, relaxed, and genuinely Caribbean. Admiralty Bay is lined with waterfront restaurants, colorful local fishing boats, boutique shops, and friendly locals.
What to Do
• Walk the Belmont Walkway
• Visit the famous model boat builders
• Explore Port Elizabeth
• Enjoy cocktails at Jack's Beach Bar
• Watch sunset from Princess Margaret Beach
Special Highlights
Princess Margaret Beach is widely considered one of the most beautiful beaches in the Grenadines. Crystal-clear water and powder-soft sand make it the perfect introduction to the week ahead.
Overnight
Anchorage: Admiralty Bay
Why:
• Excellent holding
• Well protected
• Close to restaurants and town
• Beautiful nighttime atmosphere
Day 2: Bequia → Mustique
Distance: 13 NM
Sailing Time: 2.2 Hours
Why Mustique?
Mustique is the Caribbean's most famous private island.
Owned and managed by the Mustique Company, it has hosted royalty, celebrities, and billionaires for decades. Yet visiting sailors are warmly welcomed.
What to Do
• Tour the island by golf cart
• Visit the legendary Basil's Bar
• Swim at Macaroni Beach
• Explore hidden coves
• Sunset cocktails overlooking Britannia Bay
Special Highlights
Many visitors never see the island's luxury villas hidden in the hills. Some are among the most expensive private homes in the Caribbean.
Overnight
Anchorage: Britannia Bay
Why:
• Secure moorings
• Easy shore access
• Calm conditions
• Excellent sunset views
Distance: 13 NM
Sailing Time: 2.2 Hours
Why Mustique?
Mustique is the Caribbean's most famous private island.
Owned and managed by the Mustique Company, it has hosted royalty, celebrities, and billionaires for decades. Yet visiting sailors are warmly welcomed.
What to Do
• Tour the island by golf cart
• Visit the legendary Basil's Bar
• Swim at Macaroni Beach
• Explore hidden coves
• Sunset cocktails overlooking Britannia Bay
Special Highlights
Many visitors never see the island's luxury villas hidden in the hills. Some are among the most expensive private homes in the Caribbean.
Overnight
Anchorage: Britannia Bay
Why:
• Secure moorings
• Easy shore access
• Calm conditions
• Excellent sunset views
Day 3: Mustique → Tobago Cays
Distance: 17 NM
Sailing Time: 3 Hours
Why Tobago Cays?
This is the crown jewel of the entire Grenadines.
Many experienced charter guests describe Tobago Cays as the most beautiful anchorage they have ever seen.
The protected marine park consists of five uninhabited islands surrounded by a horseshoe reef that creates a vast natural swimming pool.
What to Do
• Swim with sea turtles
• Snorkel Horseshoe Reef
• Paddleboard across turquoise lagoons
• Beach picnic on Baradal Island
• Sunset beach barbecue
Special Highlights
The sea turtle population is extraordinary. Encounters are almost guaranteed.
Overnight
Mooring: Tobago Cays Marine Park
Why:
• Spectacular scenery
• Protected waters
• Unmatched stargazing
• No light pollution
Distance: 17 NM
Sailing Time: 3 Hours
Why Tobago Cays?
This is the crown jewel of the entire Grenadines.
Many experienced charter guests describe Tobago Cays as the most beautiful anchorage they have ever seen.
The protected marine park consists of five uninhabited islands surrounded by a horseshoe reef that creates a vast natural swimming pool.
What to Do
• Swim with sea turtles
• Snorkel Horseshoe Reef
• Paddleboard across turquoise lagoons
• Beach picnic on Baradal Island
• Sunset beach barbecue
Special Highlights
The sea turtle population is extraordinary. Encounters are almost guaranteed.
Overnight
Mooring: Tobago Cays Marine Park
Why:
• Spectacular scenery
• Protected waters
• Unmatched stargazing
• No light pollution
Day 4: Tobago Cays → Petit St. Vincent
Distance: 8 NM
Sailing Time: 1.3 Hours
Morning reserved for enjoying Tobago Cays before a short afternoon sail.
Why Petit St. Vincent?
A private island resort occupies nearly the entire island.
This is barefoot luxury at its finest.
What to Do
• Spa treatments
• Fine dining
• Beachcombing
• Snorkeling nearby reefs
• Kayaking
Special Highlights
The resort famously operates with almost no visible technology. Guests traditionally communicate requests using colored flags.
Overnight
Anchorage: Petit St. Vincent
Why:
• Peaceful
• Excellent protection
• Luxury resort access
• Outstanding sunset views
Distance: 8 NM
Sailing Time: 1.3 Hours
Morning reserved for enjoying Tobago Cays before a short afternoon sail.
Why Petit St. Vincent?
A private island resort occupies nearly the entire island.
This is barefoot luxury at its finest.
What to Do
• Spa treatments
• Fine dining
• Beachcombing
• Snorkeling nearby reefs
• Kayaking
Special Highlights
The resort famously operates with almost no visible technology. Guests traditionally communicate requests using colored flags.
Overnight
Anchorage: Petit St. Vincent
Why:
• Peaceful
• Excellent protection
• Luxury resort access
• Outstanding sunset views
Day 5: Petit St. Vincent → Union Island → Chatham Bay
Distance: 10 NM
Sailing Time: 1.7 Hours
Why Union Island?
The Grenadines' most vibrant local island.
The dramatic volcanic peaks make it look more like a miniature South Pacific island than the Caribbean.
What to Do
• Visit Clifton
• Browse local markets
• Explore Happy Island
• Provision if needed
After lunch, continue to Chatham Bay.
Why Chatham Bay?
One of the Caribbean's finest anchorages.
No town. No traffic. No development.
Just a long white beach and green hills.
Special Highlights
The sunsets here are among the best in the entire Eastern Caribbean.
Overnight
Anchorage: Chatham Bay
Why:
• Excellent protection
• Quiet
• Great snorkeling
• Outstanding beach restaurants
Distance: 10 NM
Sailing Time: 1.7 Hours
Why Union Island?
The Grenadines' most vibrant local island.
The dramatic volcanic peaks make it look more like a miniature South Pacific island than the Caribbean.
What to Do
• Visit Clifton
• Browse local markets
• Explore Happy Island
• Provision if needed
After lunch, continue to Chatham Bay.
Why Chatham Bay?
One of the Caribbean's finest anchorages.
No town. No traffic. No development.
Just a long white beach and green hills.
Special Highlights
The sunsets here are among the best in the entire Eastern Caribbean.
Overnight
Anchorage: Chatham Bay
Why:
• Excellent protection
• Quiet
• Great snorkeling
• Outstanding beach restaurants
Day 6: Chatham Bay → Mayreau
Distance: 8 NM
Sailing Time: 1.3 Hours
Why Mayreau?
The smallest inhabited island in the Grenadines.
Population: roughly 250 people.
There is only one road, one village, and an incredible sense of stepping back in time.
What to Do
• Visit Salt Whistle Bay
• Walk to the hilltop church
• Panoramic photography
• Local beach bars
Special Highlights
The church viewpoint provides one of the most famous panoramas in the Caribbean, overlooking Tobago Cays and the reef system.
Overnight
Anchorage: Salt Whistle Bay
Why:
• Iconic anchorage
• Protected waters
• Palm-lined beach
• Excellent swimming
Distance: 8 NM
Sailing Time: 1.3 Hours
Why Mayreau?
The smallest inhabited island in the Grenadines.
Population: roughly 250 people.
There is only one road, one village, and an incredible sense of stepping back in time.
What to Do
• Visit Salt Whistle Bay
• Walk to the hilltop church
• Panoramic photography
• Local beach bars
Special Highlights
The church viewpoint provides one of the most famous panoramas in the Caribbean, overlooking Tobago Cays and the reef system.
Overnight
Anchorage: Salt Whistle Bay
Why:
• Iconic anchorage
• Protected waters
• Palm-lined beach
• Excellent swimming
Day 7: Mayreau → Canouan
Distance: 15 NM
Sailing Time: 2.5 Hours
Why Canouan?
Canouan combines luxury and natural beauty better than any other island in the Grenadines.
The island has evolved into one of the Caribbean's most exclusive destinations.
What to Do
• Visit the marina
• Explore Sandy Lane Marina
• Beach club lunch
• Golf course views
• Watersports
Special Highlights
The marina regularly hosts superyachts worth tens and sometimes hundreds of millions of dollars.
Overnight
Marina: Sandy Lane Yacht Club
Why:
• First-class facilities
• Fuel and water
• Luxury restaurants
• Easy preparation for the return voyage
Distance: 15 NM
Sailing Time: 2.5 Hours
Why Canouan?
Canouan combines luxury and natural beauty better than any other island in the Grenadines.
The island has evolved into one of the Caribbean's most exclusive destinations.
What to Do
• Visit the marina
• Explore Sandy Lane Marina
• Beach club lunch
• Golf course views
• Watersports
Special Highlights
The marina regularly hosts superyachts worth tens and sometimes hundreds of millions of dollars.
Overnight
Marina: Sandy Lane Yacht Club
Why:
• First-class facilities
• Fuel and water
• Luxury restaurants
• Easy preparation for the return voyage
Day 8: Canouan → Blue Lagoon (St. Vincent)
Distance: 26 NM
Sailing Time: 4.3 Hours
A beautiful final sail northward along the Grenadine chain.
The route provides excellent opportunities for:
• Dolphin sightings
• Offshore sailing
• Final swimming stop
• Spectacular views of the Grenadines fading into the horizon
Arrival at Blue Lagoon by early afternoon for disembarkation.
Distance: 26 NM
Sailing Time: 4.3 Hours
A beautiful final sail northward along the Grenadine chain.
The route provides excellent opportunities for:
• Dolphin sightings
• Offshore sailing
• Final swimming stop
• Spectacular views of the Grenadines fading into the horizon
Arrival at Blue Lagoon by early afternoon for disembarkation.
Total Voyage Statistics
Total Distance: 106 Nautical Miles
At a comfortable average of 6 knots, this itinerary delivers the best combination of:
• World-class snorkeling
• Sea turtle encounters
• Exclusive private islands
• Authentic Caribbean culture
• Luxury beach clubs
• Spectacular anchorages
• Short, enjoyable sailing days
Day | Route | Distance |
1 | Blue Lagoon → Bequia | 9 NM |
2 | Bequia → Mustique | 13 NM |
3 | Mustique → Tobago Cays | 17 NM |
4 | Tobago Cays → Petit St. Vincent | 8 NM |
5 | Petit St. Vincent → Union Island → Chatham Bay | 10 NM |
6 | Chatham Bay → Mayreau | 8 NM |
7 | Mayreau → Canouan | 15 NM |
8 | Canouan → Blue Lagoon | 26 NM |
Total Distance: 106 Nautical Miles
At a comfortable average of 6 knots, this itinerary delivers the best combination of:
• World-class snorkeling
• Sea turtle encounters
• Exclusive private islands
• Authentic Caribbean culture
• Luxury beach clubs
• Spectacular anchorages
• Short, enjoyable sailing days
Among hundreds of Caribbean charter itineraries, this route consistently ranks near the top for guests seeking the highest ratio of natural beauty to sailing effort.
Many veteran captains consider the stretch from Mustique through Tobago Cays, Mayreau, and Union Island to be the most beautiful 50 nautical miles in the entire Caribbean. After sailing these waters countless times, I find it difficult to disagree.
Oleg Drizen, RYA and IYT Yacht Master Offshore and Ocean, Skipper
Many veteran captains consider the stretch from Mustique through Tobago Cays, Mayreau, and Union Island to be the most beautiful 50 nautical miles in the entire Caribbean. After sailing these waters countless times, I find it difficult to disagree.
Oleg Drizen, RYA and IYT Yacht Master Offshore and Ocean, Skipper
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