The Ultimate 14-Night Leeward Islands Expedition
The Caribbean Voyage Most Sailors Never Have Time to Take
This is the voyage for travelers who want to experience the remarkable diversity of the northeastern Caribbean in a single journey. Over fourteen nights, the landscape changes repeatedly. French harbors give way to volcanic cliffs. Chic beach clubs are replaced by deserted anchorages. Sophisticated waterfront towns fade into view before disappearing behind the stern as another island emerges on the horizon.
THIS IS NOT SIMPLY A SAILING VACATION. IT IS A TRUE CARIBBEAN EXPEDITION
Most Caribbean charters are designed around a single island group: a week in the Grenadines. A week around St. Martin. A week in the Virgin Islands. They're wonderful experiences, but they only reveal a small chapter of a much larger story.
The Leeward Islands Expedition is different.
This is the voyage for travelers who want to experience the remarkable diversity of the northeastern Caribbean in a single journey. Over fourteen nights, the landscape changes repeatedly. French harbors give way to volcanic cliffs. Chic beach clubs are replaced by deserted anchorages. Sophisticated waterfront towns fade into view before disappearing behind the stern as another island emerges on the horizon.
On this route, no two days feel alike: one morning you may be enjoying fresh croissants in a French café overlooking a marina. The next day, you're hiking the rim of a dormant volcano. A few days later, you're snorkeling above pristine reefs with no other boats in sight.
Designed specifically for fully crewed luxury sailing catamarans between 50 and 60 feet, this itinerary combines comfortable passages, exceptional anchorages, gourmet dining, world-class snorkeling, fascinating history, and some of the most varied scenery in the Caribbean.
Beginning and ending in Saint Martin, the route explores Anguilla, St. Barts, Saba, Sint Eustatius, St. Kitts, Nevis, Antigua, Barbuda, Montserrat, and Guadeloupe before returning north.
This is not simply a sailing vacation. It is a true Caribbean expedition.
Most Caribbean charters are designed around a single island group: a week in the Grenadines. A week around St. Martin. A week in the Virgin Islands. They're wonderful experiences, but they only reveal a small chapter of a much larger story.
The Leeward Islands Expedition is different.
This is the voyage for travelers who want to experience the remarkable diversity of the northeastern Caribbean in a single journey. Over fourteen nights, the landscape changes repeatedly. French harbors give way to volcanic cliffs. Chic beach clubs are replaced by deserted anchorages. Sophisticated waterfront towns fade into view before disappearing behind the stern as another island emerges on the horizon.
On this route, no two days feel alike: one morning you may be enjoying fresh croissants in a French café overlooking a marina. The next day, you're hiking the rim of a dormant volcano. A few days later, you're snorkeling above pristine reefs with no other boats in sight.
Designed specifically for fully crewed luxury sailing catamarans between 50 and 60 feet, this itinerary combines comfortable passages, exceptional anchorages, gourmet dining, world-class snorkeling, fascinating history, and some of the most varied scenery in the Caribbean.
Beginning and ending in Saint Martin, the route explores Anguilla, St. Barts, Saba, Sint Eustatius, St. Kitts, Nevis, Antigua, Barbuda, Montserrat, and Guadeloupe before returning north.
This is not simply a sailing vacation. It is a true Caribbean expedition.
Saint Martin, Marigot Bay → Tintamarre → Pinel Island → Anguilla → Prickly Pear Cays → St. Barts → Saint Martin, Simpson Bay
RECOMMENDED 7-NIGHT SAINT MARTIN, ANGUILLA & ST. BARTS SAILING ITINERARY
Day 1: Marigot Bay, Saint Martin → Grand Case
Distance: 8 NM
Sailing Time: 1.5 Hours
Why Saint Martin?
Saint Martin is unlike anywhere else in the Caribbean.
Shared between France and the Netherlands, the island combines European sophistication with Caribbean charm. Luxury boutiques, gourmet restaurants, beach bars, and stunning anchorages coexist within a remarkably compact cruising area.
What to Do
• Explore charming Marigot
• Visit the waterfront markets
• Enjoy lunch at a beachside restaurant
• Swim at Grand Case Beach
• Watch sunset over Creole Rock
Special Highlights
Grand Case is often called the culinary capital of the Caribbean.
Many experienced travelers consider the dining scene here superior to islands several times its size.
Overnight
Anchorage: Grand Case
Why:
• Excellent protection
• Beautiful sunsets
• Easy access to restaurants
• Charming waterfront atmosphere
Distance: 8 NM
Sailing Time: 1.5 Hours
Why Saint Martin?
Saint Martin is unlike anywhere else in the Caribbean.
Shared between France and the Netherlands, the island combines European sophistication with Caribbean charm. Luxury boutiques, gourmet restaurants, beach bars, and stunning anchorages coexist within a remarkably compact cruising area.
What to Do
• Explore charming Marigot
• Visit the waterfront markets
• Enjoy lunch at a beachside restaurant
• Swim at Grand Case Beach
• Watch sunset over Creole Rock
Special Highlights
Grand Case is often called the culinary capital of the Caribbean.
Many experienced travelers consider the dining scene here superior to islands several times its size.
Overnight
Anchorage: Grand Case
Why:
• Excellent protection
• Beautiful sunsets
• Easy access to restaurants
• Charming waterfront atmosphere
Day 2: Grand Case → Tintamarre → Pinel Island
Distance: 12 NM
Sailing Time: 2 Hours
Why Tintamarre?
Tintamarre is an uninhabited island located just offshore from Saint Martin.
Its remote beaches, turquoise waters, and abundant marine life create the feeling of discovering a forgotten Caribbean paradise.
What to Do
• Snorkel with sea turtles
• Paddleboard along deserted beaches
• Explore the island trails
• Beach picnic prepared by your chef
Why Pinel Island?
Pinel offers one of the most relaxed and picturesque anchorages in Saint Martin.
Special Highlights
The contrast between wild Tintamarre and lively Pinel perfectly captures the diversity of this cruising area.
Overnight
Anchorage: Pinel Island
Why:
• Calm overnight conditions
• Excellent swimming
• Protected waters
• Beautiful scenery
Distance: 12 NM
Sailing Time: 2 Hours
Why Tintamarre?
Tintamarre is an uninhabited island located just offshore from Saint Martin.
Its remote beaches, turquoise waters, and abundant marine life create the feeling of discovering a forgotten Caribbean paradise.
What to Do
• Snorkel with sea turtles
• Paddleboard along deserted beaches
• Explore the island trails
• Beach picnic prepared by your chef
Why Pinel Island?
Pinel offers one of the most relaxed and picturesque anchorages in Saint Martin.
Special Highlights
The contrast between wild Tintamarre and lively Pinel perfectly captures the diversity of this cruising area.
Overnight
Anchorage: Pinel Island
Why:
• Calm overnight conditions
• Excellent swimming
• Protected waters
• Beautiful scenery
Day 3: Pinel Island → Road Bay, Anguilla
Distance: 14 NM
Sailing Time: 2.5 Hours
Why Anguilla?
Ask seasoned Caribbean travelers where to find the region's finest beaches, and many will answer the same way: Anguilla. This island is famous for long stretches of powder-soft white sand and astonishingly clear water.
What to Do
• Visit Shoal Bay
• Explore Sandy Ground
• Enjoy beach bars and restaurants
• Relax on uncrowded beaches
Special Highlights
Anguilla has managed to maintain an exclusive atmosphere without feeling pretentious.
Overnight
Anchorage: Road Bay
Why:
• Excellent holding
• Convenient shore access
• Great restaurants nearby
• Authentic island atmosphere
Distance: 14 NM
Sailing Time: 2.5 Hours
Why Anguilla?
Ask seasoned Caribbean travelers where to find the region's finest beaches, and many will answer the same way: Anguilla. This island is famous for long stretches of powder-soft white sand and astonishingly clear water.
What to Do
• Visit Shoal Bay
• Explore Sandy Ground
• Enjoy beach bars and restaurants
• Relax on uncrowded beaches
Special Highlights
Anguilla has managed to maintain an exclusive atmosphere without feeling pretentious.
Overnight
Anchorage: Road Bay
Why:
• Excellent holding
• Convenient shore access
• Great restaurants nearby
• Authentic island atmosphere
Day 4: Anguilla → Prickly Pear Cays
Distance: 8 NM
Sailing Time: 1.5 Hours
Why Prickly Pear?
Prickly Pear is exactly what many people imagine when they dream about the Caribbean. Tiny islands. White sand. Turquoise water. Virtually no development.
What to Do
• Snorkeling
• Seabob adventures
• Paddleboarding
• Floating beach day
• Sunset cocktails onboard
Special Highlights
The water clarity here is among the best anywhere in the Caribbean.
Overnight
Anchorage: Prickly Pear Cays
Why:
• Secluded setting
• Exceptional water clarity
• Incredible stargazing
• Minimal boat traffic
Distance: 8 NM
Sailing Time: 1.5 Hours
Why Prickly Pear?
Prickly Pear is exactly what many people imagine when they dream about the Caribbean. Tiny islands. White sand. Turquoise water. Virtually no development.
What to Do
• Snorkeling
• Seabob adventures
• Paddleboarding
• Floating beach day
• Sunset cocktails onboard
Special Highlights
The water clarity here is among the best anywhere in the Caribbean.
Overnight
Anchorage: Prickly Pear Cays
Why:
• Secluded setting
• Exceptional water clarity
• Incredible stargazing
• Minimal boat traffic
Day 5: Prickly Pear → Gustavia, St. Barts
Distance: 18 NM
Sailing Time: 3 Hours
Why St. Barts?
St. Barts is the crown jewel of luxury Caribbean travel. The island combines French elegance, world-class dining, designer boutiques, luxury villas, and spectacular beaches. Unlike many luxury destinations, St. Barts remains genuinely beautiful from the water.
What to Do
• Explore Gustavia
• Visit designer boutiques
• Enjoy waterfront dining
• Beach clubs at St. Jean
• Sunset cocktails overlooking the harbor
Special Highlights
The harbor often hosts some of the most impressive superyachts in the world.
Overnight
Anchorage: Gustavia Harbor
Why:
• Iconic destination
• Excellent dining
• Vibrant atmosphere
• Prime location
Distance: 18 NM
Sailing Time: 3 Hours
Why St. Barts?
St. Barts is the crown jewel of luxury Caribbean travel. The island combines French elegance, world-class dining, designer boutiques, luxury villas, and spectacular beaches. Unlike many luxury destinations, St. Barts remains genuinely beautiful from the water.
What to Do
• Explore Gustavia
• Visit designer boutiques
• Enjoy waterfront dining
• Beach clubs at St. Jean
• Sunset cocktails overlooking the harbor
Special Highlights
The harbor often hosts some of the most impressive superyachts in the world.
Overnight
Anchorage: Gustavia Harbor
Why:
• Iconic destination
• Excellent dining
• Vibrant atmosphere
• Prime location
Day 6: Explore St. Barts
Distance: 6 NM
Sailing Time: 1 Hour
Why Spend Two Days?
Many itineraries rush through St. Barts. That's a mistake. The island deserves time.
What to Do
• Colombier Beach
• Gouverneur Beach
• St. Jean Beach
• Luxury beach clubs
• Island sightseeing
Special Highlights
Colombier Bay remains one of the most beautiful anchorages in the Caribbean and is accessible primarily by boat.
Overnight
Anchorage: Colombier Bay
Why:
• Spectacular scenery
• Excellent snorkeling
• Quiet evening atmosphere
• Unforgettable sunsets
Distance: 6 NM
Sailing Time: 1 Hour
Why Spend Two Days?
Many itineraries rush through St. Barts. That's a mistake. The island deserves time.
What to Do
• Colombier Beach
• Gouverneur Beach
• St. Jean Beach
• Luxury beach clubs
• Island sightseeing
Special Highlights
Colombier Bay remains one of the most beautiful anchorages in the Caribbean and is accessible primarily by boat.
Overnight
Anchorage: Colombier Bay
Why:
• Spectacular scenery
• Excellent snorkeling
• Quiet evening atmosphere
• Unforgettable sunsets
Day 7: St. Barts → Simpson Bay, Saint Martin
Distance: 15 NM
Sailing Time: 2.5 Hours
Why Return to Saint Martin?
The final evening provides a perfect opportunity to enjoy one last celebration aboard.
What to Do
• Simpson Bay nightlife
• Waterfront dining
• Sunset cruise
• Final swim
Special Highlights
The approach to Simpson Bay is one of the most iconic arrivals in Caribbean sailing.
Overnight
Anchorage: Simpson Bay Lagoon
Why:
• Well protected
• Convenient departure location
• Excellent facilities
• Vibrant atmosphere
Distance: 15 NM
Sailing Time: 2.5 Hours
Why Return to Saint Martin?
The final evening provides a perfect opportunity to enjoy one last celebration aboard.
What to Do
• Simpson Bay nightlife
• Waterfront dining
• Sunset cruise
• Final swim
Special Highlights
The approach to Simpson Bay is one of the most iconic arrivals in Caribbean sailing.
Overnight
Anchorage: Simpson Bay Lagoon
Why:
• Well protected
• Convenient departure location
• Excellent facilities
• Vibrant atmosphere
Day 8: Simpson Bay → Marina Fort Louis
Distance: 5 NM
Sailing Time: 1 Hour
A short and relaxing final sail before disembarkation.
Arrival at Marina Fort Louis by early afternoon for disembarkation.
Distance: 5 NM
Sailing Time: 1 Hour
A short and relaxing final sail before disembarkation.
Arrival at Marina Fort Louis by early afternoon for disembarkation.
Total Voyage Statistics
Total Distance: 86 Nautical Miles
At a comfortable average of 6 knots, this itinerary delivers the perfect combination of:
• World-class beaches
• European sophistication
• Luxury beach clubs
• Exceptional dining
• Crystal-clear anchorages
• Secluded islands
• Short, enjoyable sailing days
Among all Caribbean luxury charter destinations, few itineraries offer more variety with less sailing effort.
Many experienced captains consider the triangle formed by Saint Martin, Anguilla, and St. Barts to be the finest luxury cruising area in the Caribbean.
For guests seeking beautiful sailing combined with world-class dining, vibrant culture, and unforgettable anchorages, it is difficult to imagine a better week on the water.
Day | Route | Distance |
1 | Marigot Bay → Grand Case | 8 NM |
2 | Grand Case → Tintamarre → Pinel | 12 NM |
3 | Pinel → Anguilla | 14 NM |
4 | Anguilla → Prickly Pear Cays | 8 NM |
5 | Prickly Pear → St. Barts | 18 NM |
6 | Explore St. Barts | 6 NM |
7 | St. Barts → Simpson Bay | 15 NM |
8 | Simpson Bay → Marina Fort Louis | 5 NM |
Total Distance: 86 Nautical Miles
At a comfortable average of 6 knots, this itinerary delivers the perfect combination of:
• World-class beaches
• European sophistication
• Luxury beach clubs
• Exceptional dining
• Crystal-clear anchorages
• Secluded islands
• Short, enjoyable sailing days
Among all Caribbean luxury charter destinations, few itineraries offer more variety with less sailing effort.
Many experienced captains consider the triangle formed by Saint Martin, Anguilla, and St. Barts to be the finest luxury cruising area in the Caribbean.
For guests seeking beautiful sailing combined with world-class dining, vibrant culture, and unforgettable anchorages, it is difficult to imagine a better week on the water.
Let's Start Planning Your Charter
Every charter we arrange is customized to match your travel style, preferred activities, pace, and expectations.
Whether you dream of beach clubs in St. Barts, secluded anchorages in Anguilla, gourmet dining in Saint Martin, or simply relaxing aboard a fully crewed luxury sailing catamaran, our team will help create an itinerary perfectly tailored to you.
Contact Emerald Sail today and let's start planning your unforgettable Caribbean sailing adventure.
Oleg Drizen, RYA and IYT Yacht Master Offshore and Ocean, Skipper
Every charter we arrange is customized to match your travel style, preferred activities, pace, and expectations.
Whether you dream of beach clubs in St. Barts, secluded anchorages in Anguilla, gourmet dining in Saint Martin, or simply relaxing aboard a fully crewed luxury sailing catamaran, our team will help create an itinerary perfectly tailored to you.
Contact Emerald Sail today and let's start planning your unforgettable Caribbean sailing adventure.
Oleg Drizen, RYA and IYT Yacht Master Offshore and Ocean, Skipper
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