5-Day Anguilla & St. Martin Yacht Charter: Island Hopping in the Northern Leeward Islands
Experience a dynamic Anguilla yacht charter combined with the vibrant energy of St. Martin, exploring the northern Leeward Islands. This itinerary blends Anguilla's serene beaches with St. Martin's unique Franco-Dutch charm and bustling marinas. Glide across azure waters, savour diverse cuisines, and immerse yourself in two distinct island cultures. An Anguilla yacht charter provides access to secluded anchorages and lively towns, crafting a truly diverse Caribbean adventure.
Cruising region: Caribbean Yacht Charter
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Plan this charter
- First planned stop
- Marigot Bay, St. Martin (French side)
- Final planned stop
- Simpson Bay, St. Maarten (Dutch side)
Shore plans to discuss with your crew
- Day 1Boarding your yacht
- Day 1Exploring Marigot market
- Day 1Visit Fort Louis
- Day 1French patisserie treats
- Day 2Swimming and sunbathing
- Day 2Snorkelling Grand Case Bay
Confirm joining and departure ports, yacht availability and the daily passage plan before paying a deposit. The captain decides anchorages and any route changes for weather, sea conditions and local restrictions. Shore venues, marine-park permissions and activity bookings require separate confirmation.
Map connections are schematic, not a navigable passage plan. Distances, safe approaches and passage times must be checked by the captain.
Ask for an itemised quotation covering the charter fee, taxes, APA or package expenses, berth charges and any delivery or redelivery costs.
- DAY 01
Marigot Bay, St. Martin (French side)
Begin your journey in the charming French capital of Marigot, St. Martin. Board your yacht and soak in the European atmosphere, exploring the local market and historic Fort Louis.
- Boarding your yacht
- Exploring Marigot market
- Visit Fort Louis
- French patisserie treats
- Anchorage
- Port La Royale Marina
- Dining
- Le Bistrot Caraïbes
- DAY 02
Grand Case, St. Martin (French side)
Sail to Grand Case, known as the 'Gourmet Capital of the Caribbean'. Spend the day enjoying its beautiful beach and preparing for an evening of exquisite dining.
- Swimming and sunbathing
- Snorkelling Grand Case Bay
- Exploring the art galleries
- Sunset cocktails on the beach
- Anchorage
- Grand Case Bay
- Dining
- L'Esprit de Jean-Claude
- DAY 03
Road Bay, Anguilla
Make the short crossing to Anguilla and clear customs at Road Bay. Spend the afternoon relaxing on the beach or exploring the island's main port.
- Crossing the Anguilla Channel
- Customs clearance
- Relaxing on Road Bay beach
- Enjoying local music
- Anchorage
- Road Bay
- Dining
- Blanchard's Beach Shack
- DAY 04
Sandy Ground & Little Bay, Anguilla
From Sandy Ground, take the tender to the hidden gem of Little Bay, a dramatic cove perfect for snorkelling and cliff jumping. Enjoy the secluded beauty.
- Tender ride to Little Bay
- Snorkelling with turtles
- Exploring the sea caves
- Relaxing on the small beach
- Anchorage
- Sandy Ground
- Dining
- Dune Preserve
- DAY 05
Simpson Bay, St. Maarten (Dutch side)
Return to St. Maarten, anchoring in bustling Simpson Bay. Enjoy the lively atmosphere, watersports, and duty-free shopping before your departure.
- Watersports in Simpson Bay
- Duty-free shopping
- Watching planes at Maho Beach (optional)
- Farewell dinner on board or ashore
- Anchorage
- Simpson Bay Lagoon
- Dining
- Skipjack's
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