St. Maarten/St. Barth’s/Anguilla
The Leeward Islands in the Caribbean are a favorite home base of charter yachts each winter, when guests flock to enjoy the quiet harbors, pretty beaches, and warm sunshine. Many islands remain minimally developed, while others offer world-class dining and shopping. A yacht charter here can truly be anything that you want it to be, whether you are interested in “getting away from it all” or sampling the finest of the Caribbean’s culture. If you have already chartered in the British Virgin Islands and are looking for a new destination to try out, The Leeward Islands is often close enough so that you can explore a new region while still enjoying your favorite Virgin Island yacht and crew.
WHERE CAN WE GO?
7-Night Leeward Islands Crewed Yacht Charter Itinerary
St. Martin • Anguilla • St. Barth’s
Average Cruising Speed: 8 knots
Daily Sailing Time: 2–4 hours
Route Style: Protected anchorages & short scenic island hops
Day 1 — St. Martin → Anguilla (Road Bay)
Distance: 12 NM
Cruising Time: ~1 hr 30 min
Your crew welcomes you aboard in St. Martin, one of the Caribbean’s premier yachting hubs. After a safety briefing and settling into your cabins, set sail north across the Anguilla Channel.
Arrive at Road Bay in Anguilla, known for powder-soft sand and calm waters. Spend the afternoon swimming or relaxing on deck with a cocktail as the sun dips over the horizon.
Optional evening ashore:
• Dinner at Blanchards Beach Shack or Sandy Ground restaurants
• Beach walk along the quiet shoreline
Day 2 — Anguilla → Prickly Pear Cays
Distance: 8 NM
Cruising Time: ~1 hr
Enjoy a leisurely breakfast before sailing to the Prickly Pear Cays, an uninhabited marine park with some of the clearest water in the Leeward Islands.
Highlights include:
• Exceptional snorkeling reefs
• Paddleboarding and kayaking in protected turquoise lagoons
• Relaxed beach barbecue prepared by your chef
Spend the evening under the stars in this peaceful anchorage.
Day 3 — Prickly Pear → St. Barth’s (Gustavia)
Distance: 24 NM
Cruising Time: ~3 hrs
Set sail southeast toward the glamorous island of St. Barthélemy (St. Barth’s). Arrive in Gustavia Harbor, famous for its superyachts, chic boutiques, and French-Caribbean charm.
Afternoon options:
• Shopping in designer boutiques
• Beach time at Shell Beach
• Sunset cocktails overlooking the harbor
Dinner ashore offers world-class French cuisine.
Day 4 — Gustavia → Colombier Bay
Distance: 4 NM
Cruising Time: ~30 min
A short scenic cruise brings you to Colombier Bay, one of the most protected anchorages on St. Barth’s. Surrounded by green hills and accessible only by boat or hiking trail, this bay feels wonderfully secluded.
Activities:
• Snorkeling with sea turtles
• Paddleboarding along the cliffs
• Relaxing on the yacht’s floating dock
Enjoy a quiet evening onboard with dinner under the stars.
Day 5 — Colombier → Grand Case (St. Martin)
Distance: 15 NM
Cruising Time: ~2 hrs
Cruise back toward St. Martin, arriving in Grand Case, often called the culinary capital of the Caribbean.
Afternoon highlights:
• Beach bars and calm swimming
• Creole bakeries and cafés
• Optional sunset stroll through the charming waterfront village
Dinner ashore is highly recommended at one of the island’s renowned French restaurants.
Day 6 — Grand Case → Tintamarre
Distance: 8 NM
Cruising Time: ~1 hr
Sail to Tintamarre Island, a protected nature reserve with calm anchorages and long natural beaches.
Things to enjoy:
• Snorkeling with turtles
• Exploring deserted beaches
• Kayaking and paddleboarding in protected waters
This tranquil stop offers a true “desert island” experience.
Day 7 — Tintamarre → Simpson Bay Lagoon (St. Martin)
Distance: 10 NM
Cruising Time: ~1 hr 30 min
Return toward Simpson Bay Lagoon, one of the largest and most protected natural harbors in the Caribbean.
Spend your final afternoon:
• Enjoying water sports
• Visiting beach clubs at Maho or Mullet Bay
• Celebrating your last evening with a farewell dinner prepared by your chef.
Day 8 — Disembarkation in St. Martin
Enjoy a final breakfast onboard before disembarking in St. Martin, taking with you unforgettable memories of sailing the Leeward Islands.
✔ Why This Route Works Well
Ideal for luxury crewed catamaran charters
Short comfortable sailing distances
Multiple well-protected anchorages
Combines Anguilla’s beaches, St. Barth’s glamour, and St. Martin’s dining
