LEEWARD ISLANDS SAILING GUIDE
Leeward Islands: Chic, Easy & Endlessly Blue: St. Martin • St. Barth • Anguilla & Hidden Cays
One morning you’re sipping espresso in a French patisserie, by lunch you’re swimming with turtles off an uninhabited cay, and by sunset you’re sipping a ti’ punch where rock stars try (and fail) to go unnoticed. The northern Leewards pack three countries, two currencies and a dozen personalities into a sailing area so easy, you’ll wonder why you didn’t do this sooner.
With steady trade winds, line-of-sight hops and calm turquoise passages, the Leeward Islands around St. Martin, St. Barth and Anguilla are the Caribbean’s most stylish playground - short sails, big rewards. Think designer boutiques and beach bars, coral gardens and gin-clear lagoons, and an island where the runway is part of the show. If the Windwards are dramatic, the Leewards are deliciously effortless.
Where to start your Leeward Islands sailing holiday
Leeward Islands sailing holiday tips
Recommended 7-night Leeward Islands sailing itinerary
The Leewards enjoy a classic inter-tropical climate: sunny, warm and remarkably stable. Daytime temperatures hover 77–86°F (25–30°C) year-round, and sea temperature is 79–84°F (26–29°C). Easterly trade winds are your engine - typically 15–20 knots in winter, 10–15 knots in summer - giving you perfect beam reaches between islands and flat-water fun inside the lagoons.
The best sailing season is mid-December to May. You’ll get steady breezes, minimal rain, and that famous 60-mile visibility - you can literally see St. Barth from St. Martin. Peak buzz is late December–April, with regattas and full marinas. For fewer crowds and softer prices, aim for late April–June and November - still excellent, just quieter.
Hurricane season is June to November (highest risk late August–October). Many boats stay available with discounts, but you’ll need weather flexibility. And a heads-up: winter winds can hit 25–30 knots during Christmas winds - thrilling for experienced crews, so tell us your comfort level, and we’ll pick the right yacht and route.
Start from St. Martin - the world’s smallest bi-national island (French Saint-Martin to the north, Dutch Sint Maarten to the south) and the Leewards’ charter capital. Bases are Marina Fort Louis in Marigot (French side, charming and chic) and Marina Port La Royale or Simpson Bay Marina (Dutch side, lively and full-service). Both are excellent.
Fly into Princess Juliana International Airport (SXM) - yes, the one with the famous low beach landings. Non-stop flights from Miami, New York, Atlanta, Charlotte and Paris, plus connections through San Juan (SJU). Transfer to Marigot is ~20–30 minutes, to Simpson Bay ~10 minutes. Flying private or via St. Barth? Gustaf III Airport (SBH) connects via tiny island hoppers - a thrill in itself.
Documents are simple: a valid passport for most US, EU and UK citizens (no visa for short stays). You’ll clear immigration when you hop between French St. Martin, Dutch Sint Maarten, Anguilla (British) and St. Barth (French). Your captain handles it - just bring passports and keep the “Q” flag handy. Currency: Euro on the French side, Netherlands Antillean Guilder / USD on the Dutch side, Euro in St. Barth. USD is king almost everywhere, cards are widely accepted.
- Short hops, open-water spice. Most sails are 1–2 hours, but the channel between St. Martin and St. Barth can be choppy with Atlantic swell - morning is calmest, and catamarans love it. Inside lagoons and leeward bays it’s pancake-flat,
- Moorings everywhere, easy life. Tidal range is tiny (1–2 ft). Almost all stops use mooring buoys - just pick up and relax. Anchoring is allowed in sandy patches but check park rules (especially around Anguilla’s marine parks and St. Barth’s nature reserve),
- Provision smart. Stock up at Carrefour or Super U (Marigot) or Budget Marine-adjacent supermarkets in Simpson Bay. French side = outstanding cheese, wine and patisserie; Dutch side = big selection and US brands. Top up water/fuel in Marigot or Gustavia - both full-service,
- Island etiquette. St. Barth is glamorous but relaxed - no need for heels on deck, but a linen shirt for Gustavia dinner goes down well. Anguilla is barefoot and British-polite. And yes - you can do breakfast in France, lunch in the Netherlands and dinner in Swedish-ish St. Barth. We’ve timed it.
Captain’s tip: Don’t rush. The Leewards reward the lingerer - an extra hour snorkeling Creole Rock or a second painkiller at Sunset Beach Bar (watching those SXM landings) is never wasted.
A perfect loop from St. Martin — no long passages, maximum variety. About 90 NM total. Champagne sailing, every day.
Day 1: Marina Fort Louis, St. Martin → Tintamarre & Pinel Island
Your Decompression Day - Population: You
After briefing in Marigot, slip out for a 30-minute sail to Pinel Island - a tiny, thatched-roof paradise off the French coast. Wade ashore for grilled lobster and rum, snorkel the reef. Then drift to Tintamarre, an uninhabited nature reserve with wild goats, a deserted airstrip and a beach so white it squeaks. Anchor for the night under pure stars. This is your “are we really here?” moment - and it’s only Day 1.
Day 2: Tintamarre → Road Bay & Sandy Island, Anguilla
Anguilla: 33 Beaches and Zero Stress
A relaxed 2-hour reach northwest to Anguilla, the Caribbean’s best-kept secret. British, blissfully quiet, absurdly beautiful. Day-anchor off Sandy Island - a speck of sand with a palm-shack bar (order the rum punch, thank us later) - then clear in at Road Bay. Soak in Meads Bay and Shoal Bay East - regularly voted top beaches on the planet - where the water goes from pale aqua to deep sapphire in three steps. Dinner? Blanchards or a beach BBQ - Anguilla does low-key luxury better than anyone.
Day 3: Anguilla → Gustavia, St. Barth
Hello, St. Barth - The Riviera Went Tropical
Cross the channel (12 NM) to St. Barth (Saint-Barthélemy) and prepare to be charmed and slightly spoiled. Tiny, volcanic, French to its core - red-roofed Gustavia Harbour is a jewel box of mega-yachts, designer boutiques, and harbour-side cafés. Moor and stroll: Fort Gustav for views, Shell Beach for, well, shells, and a waterfront dinner where the wine list is thicker than the sailing guide. St. Barth knows it’s special - and somehow never brags about it.
Day 4: St. Barth → Anse de Colombier
The Beach You Have to Earn (Just a Little)
St. Barth’s best beach has no road. Anse de Colombier on the northwest tip is a protected nature reserve - accessible only by boat or a 20-minute hike, which is why it stays perfect. Turquoise water, sea turtles, rock formations that look sculpted. Snorkel the northern reef, paddle, or just do nothing at all. Your captain will call it “the best office in the Caribbean” and he’s not wrong. Sundowners here are mandatory; reservations not required.
Day 5: Colombier → Île Fourchue
Your Private Volcano for the Night
A short, exhilarating sail back toward St. Martin but with a wild-card stop: Île Fourchue, a rugged, uninhabited volcanic island halfway between St. Barth and St. Martin. It’s a marine reserve, a hike and a 360° viewpoint all in one - scramble to the ridge for sunset over both islands. Anchor in the crater-like bay, snorkel the clear boulder-strewn water, and enjoy the rarest Caribbean sound: nothing. No bars, no shops, just goats, seabirds and your crew’s laughter.
Day 6: Île Fourchue → Creole Rock & Grand Case, St. Martin
Back to French Flair & Feasting
Return to St. Martin’s French side - first a snorkel at Creole Rock off Grand Case, a celebrated marine reserve where angelfish and parrotfish dart through coral fingers in 10 ft of water. Then into Grand Case itself - the culinary capital of the Caribbean. The “Restaurant Row” strip has everything from beach shacks to Michelin-aspirant bistros (try the conch fritters and accras). Anchor off, dinghy in, and let your taste buds have their own charter.
Day 7: Grand Case → Marigot & Simpson Bay Lagoon
Last Swim, Last Shop, Last “One More Day?”
Coast south along St. Martin’s lagoon-side. Stop at Friar’s Bay for a final swim, then into Marigot for the waterfront market - spices, madras fabric, French pastries to take home. Or slip into the vast Simpson Bay Lagoon, the largest in the Caribbean, for a calm-water farewell night (and easy next-morning checkout). Watch the sunset planes skim Maho Beach - a classic St. Martin finale - and start planning who you’ll bring next time. Everyone wants a second lap.
Want more beach club? Swap Île Fourchue for an extra night in Anguilla. Want more glam? Add a second night in Gustavia. This loop flexes beautifully - just tell us your style.
FROM FRENCH MARKET TO YOUR OWN PRIVATE ISLAND — IN ONE DAY?
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That’s the Leewards. No long passages, no fuss — just chic harbours, wild cays and water so clear you’ll check your depth twice. Let Emerald Sail pick the perfect catamaran and line up your moorings. Your only job? Choose between another rosé in Gustavia or another snorkel in Colombier. (Hint: do both.)