Road Bay Harbor
Anguilla
Anguilla's primary cruising harbor and customs port, featuring a relaxed island atmosphere, excellent beaches, protected anchorage, and a welcoming gateway for sailors exploring the Northern Leeward Islands.
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Northern Leeward Islands
St. Martin • St. Barths • Anguilla
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Saint Martin
The Northern Leewards' premier cruising hub, offering world-class marinas, provisioning, customs services, and easy access to neighboring islands.
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St. Barths
Luxury marinas, elegant waterfront dining, designer shopping, and spectacular anchorages make St. Barths one of the Caribbean's most iconic sailing destinations.
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Anguilla
Peaceful anchorages, uncrowded beaches, and a relaxed island atmosphere make Anguilla a favorite stop for cruisers seeking quieter waters.
Why Cruise the Northern Leeward Islands?
Cruising Snapshot
Best Season
December–May
Sailing Difficulty
Moderate
Prevailing Winds
Easterly trade winds
Protection
Good in major harbors and selected anchorages
Customs
Multiple jurisdictions
Charter Popularity
High
Regional Orientation
Use this orientation map to quickly understand how Saint Martin, St. Barths, and Anguilla connect as a cruising region. It highlights major harbors, marinas, customs ports, and the most common island-hopping routes.
Explore Featured Harbors
Discover the Northern Leeward Islands' signature harbors, from protected lagoon anchorages and world-class marinas to charming waterfront towns that make this one of the Caribbean's premier cruising regions.
Marigot Harbor
Saint Martin (French Side)
The heart of French Saint Martin, offering convenient customs clearance, provisioning, waterfront cafés, marinas, and easy cruising access to nearby anchorages, beaches, and the island's celebrated French-Caribbean culture.
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Gustavia Harbor
Saint Barthélemy (St. Barths)
An iconic Caribbean harbor known for its picturesque waterfront, upscale marinas, boutique shopping, fine dining, and excellent access to the crystal-clear anchorages that have made St. Barths a favorite destination for sailors and yachts alike.
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Simpson Bay Lagoon
Saint Martin / Sint Maarten
The premier cruising hub of the Northern Leeward Islands, offering protected lagoon anchorages, full-service marinas, marine services, provisioning, customs, and easy access to both the French and Dutch sides of the island.
Explore Harbor →Cruising This Region
Plan your passage through this cruising region with practical notes on routes, anchorages, weather, provisioning, and customs.
Customs & Provisioning
Customs clearance is available throughout the region, with excellent provisioning, fuel, water, and marine services centered around Saint Martin. Nearby islands offer convenient clearance procedures, allowing sailors to move efficiently between destinations.
Weather & Seasons
Steady easterly trade winds provide reliable sailing throughout the primary cruising season from December through May. During summer and fall, cruisers should closely monitor tropical weather and hurricane forecasts before planning offshore passages.
Anchorages & Marinas
The region offers a mix of well-equipped marinas, protected lagoon facilities, and scenic anchorages. Simpson Bay Lagoon serves as the primary marine service center, while numerous bays throughout the islands provide comfortable overnight anchoring in suitable conditions.
Passage Planning
The Northern Leeward Islands are ideal for short island-hopping passages, with most destinations only 10–20 nautical miles apart. Cruisers commonly move between Saint Martin, St. Barths, and Anguilla in a single weather window while enjoying numerous protected overnight stops.
Essential Regional Information
Quick reference details for planning a cruise through this region, including logistics, services, currencies, and practical travel information.
Countries & Territories
Saint Martin, Sint Maarten, St. Barths, Anguilla
Languages
English, French, Dutch
Currency
Euro, US Dollar, East Caribbean Dollar
Hurricane Season
June–November
Fuel & Water
Readily available at major marinas throughout the region, with the widest selection in Saint Martin.
Provisioning
Excellent in Saint Martin; limited but adequate in St. Barths and Anguilla.
Marine Services
Full-service marinas, boatyards, chandleries, repairs, haul-outs, sail lofts, and marine technicians centered in Simpson Bay Lagoon.
Cell Coverage
Excellent throughout major islands; roaming available between jurisdictions.
Celebrate Your Favorite Harbor
Bring Your Favorite Harbor Home
Every harbor has a story worth remembering. Whether it's your home port, a favorite anchorage, or the place where an unforgettable voyage began, our Harbor Collection cutting boards are personalized to celebrate the harbors that mean the most to you.
Choose from hundreds of harbors featured throughout Harbor Atlas to create a handcrafted keepsake that brings your favorite harbor home.
Choose from hundreds of harbors featured throughout Harbor Atlas to create a handcrafted keepsake that brings your favorite harbor home.
- Personalized with your favorite harbor
- Premium acacia hardwood
- Handcrafted in Minnesota
- Perfect gift for sailors and cruising families
Featured Cruising Routes
Discover popular island-hopping passages and longer cruising routes that connect this region with neighboring destinations throughout the Caribbean.
Short Passage
Saint Martin to St. Barths
Northern Leeward Islands
A classic Northern Leewards passage connecting Saint Martin with Gustavia and the anchorages of St. Barths.
Short Passage
Saint Martin to Anguilla
Northern Leeward Islands
A short cross-channel route from Saint Martin to Anguilla, popular with cruisers looking for beaches, clear water, and a quieter island stop.
Coming Soon
Eastern Caribbean Island Chain
Caribbean
A larger island-hopping route connecting the Virgin Islands, Northern Leewards, Antigua, Guadeloupe, Dominica, Martinique, St. Lucia, the Grenadines, and Grenada.
Northern Leeward Islands Cruising FAQ
Answers to common questions about cruising, navigation, customs, and planning for this region.
What is the best time of year to cruise the Northern Leeward Islands?
The primary cruising season runs from December through May, when the northeast trade winds are most consistent and the risk of tropical storms is lowest. June through November is hurricane season, so cruisers should monitor forecasts carefully and have flexible plans.
Do I need to clear customs between Saint Martin, Anguilla, and St. Barths?
Yes. Although the islands are close together, each has its own customs and immigration requirements. Cruisers should clear in and out according to local regulations before moving between jurisdictions.
How long are the sailing passages between the Northern Leeward Islands?
Most passages are relatively short, typically ranging from 10 to 20 nautical miles. Many cruisers comfortably move between Saint Martin, St. Barths, and Anguilla during daylight hours while enjoying multiple overnight stops throughout the region.
Which harbors are the primary cruising hubs in the Northern Leeward Islands?
Simpson Bay Lagoon serves as the region's primary full-service cruising hub. Other popular destinations include Marigot on the French side of Saint Martin, Gustavia on St. Barths, and Road Bay in Anguilla, each offering customs services, marinas, anchorages, and access to local attractions.
Is the Northern Leeward Islands region suitable for newer cruising sailors?
Yes. The combination of short passages, numerous protected anchorages, well-developed marine services, and multiple customs ports makes the Northern Leeward Islands one of the Caribbean's most approachable island-hopping cruising destinations. Sailors should still monitor weather conditions and plan passages carefully.
Continue Exploring Nearby Regions
Continue your Harbor Atlas journey with nearby cruising regions, neighboring island groups, and connected sailing destinations.
U.S. Virgin Islands
Discover protected anchorages, vibrant harbors, national parks, and some of the Caribbean's most accessible island-hopping cruising.
British Virgin Islands
Explore world-famous sailing waters featuring The Baths, Norman Island, Jost Van Dyke, and countless protected anchorages.
Antigua & Barbuda
Continue south to historic Nelson's Dockyard, English Harbour, and one of the Caribbean's premier blue-water cruising destinations.
Guadeloupe
Experience French Caribbean culture, volcanic landscapes, rainforest anchorages, and exceptional cruising throughout the Guadeloupe archipelago.
