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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- 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
Knowledge graph
Where this route sits in the ecosystem
Destinations, berths and yachts connected to this itinerary — each with the reason for the link.
Destinations on this route
An itinerary is defined by the places it visits
- Anguilla Yacht Charter
Contract relationship visits -> destination recorded by the ecosystem spec; rationale normalized by Phase 2.
- Grenada Yacht Charter
Neighbouring destination in the same ecosystem, reachable on this route
- Jamaica Yacht Charter
Neighbouring destination in the same ecosystem, reachable on this route
Berths on this route
The berths the route actually calls at
- Errol Flynn Marina Boatyard
Berth available on this leg of the route
- Errol Flynn Marina
Berth available on this leg of the route
- Port Louis Marina
Berth available on this leg of the route
Build a week from this itinerary — every related page
Continue with the destinations, itineraries, marinas and practical guides that are most closely related to this page.