A Chic Yacht Getaway: St. Martin, Anguilla & St. Barts by Sea
Estimated read time: ~6 minutes
Three Islands, One Effortlessly Chic Escape
Some vacations are meant to be slow, sun-soaked, and utterly stylish. This is one of them. A sailing vacation from St. Martin to Anguilla and St. Barts is a breezy blend of French flair, British-Caribbean charm, and barefoot luxury — all within a few hours of sailing.
Each island brings something different to the table: the food, the beaches, the vibe. One moment you’re sipping rosé in Gustavia, the next you’re snorkeling off a tiny sandbar near Anguilla. And throughout it all, your yacht is your home — no unpacking, no rushing, no crowds.
English and French are widely spoken, and the sailing is smooth, the anchorages stunning, and the experiences beautifully curated — especially when you’re doing it with the right crew.
How to Get There
Fly into Princess Juliana International Airport (SXM) on the Dutch side of St. Martin. With direct flights from New York, Miami, Paris, Amsterdam, and more, it’s one of the Caribbean’s best-connected islands.
Charters typically depart from either Simpson Bay (Dutch side) or Marigot (French side). Both are within 20 minutes of the airport and offer easy access to Anguilla and St. Barts.
Because you’ll be crossing between different countries (Dutch/French St. Martin, British Anguilla, French St. Barts), the charter company and skipper will take care of customs clearances. It’s simple and part of the routine when island-hopping this region by sea.
French Cafés, Beach Bars & Remote Bays
🇫🇷 St. Martin
Start or end your trip in Grand Case, known for its beachside French restaurants and laid-back charm. Snorkel at Creole Rock, grab a grilled mahi sandwich at a “lolo” (local BBQ joint), or sip cocktails at sunset right from your cockpit.
🇦🇮 Anguilla
Anguilla is all about unhurried elegance. Anchor in Rendezvous Bay or Sandy Ground, then beach-hop to Meads Bay, Shoal Bay, or Little Bay. For something unforgettable, head to Sandy Island — a tiny cay with powdery sand, a grill shack, and reef snorkeling right off shore.
There’s a sense of understated luxury here — think barefoot dinners, clear water, and peaceful anchorages.
🇧🇱 St. Barts
Pulling into Gustavia harbor feels like arriving in St. Tropez — if St. Tropez had sea turtles and no traffic. From luxury shopping to local bakeries, from world-class cuisine to hilltop hikes, this island makes indulgence feel effortless.
Don’t miss Colombier Beach, accessible only by boat or foot, and Shell Beach, great for lunch and a swim. If you want the best of both worlds — elegance and wild beauty — you’ll find it here.
Suggested 7-Day Sailing Itinerary (Round Trip from St. Martin)
This itinerary gives you time to unwind, explore, and enjoy each island — with short sailing hours and long, golden afternoons.
Day 1: Depart St. Martin > Grand Case (1 hr)
Ease into your week with a short sail to Grand Case. Dine on the beach, grab a glass of French wine, and watch the sun dip into the sea.
Day 2: Grand Case > Anguilla - Rendezvous Bay (2.5 hrs)
Clear customs and sail to Anguilla. Drop anchor in calm waters and enjoy a lazy beach day with sunset cocktails and grilled fish.
Day 3: Explore Anguilla’s North Coast + Sandy Island (2–2.5 hrs total)
Sail or dinghy to Sandy Island, snorkel, and picnic on the sand. Continue up to Shoal Bay or stay in Meads Bay for a peaceful overnight.
Day 4: Anguilla > St. Barts (3.5 hrs)
Your longest sail of the week — a fun open-water crossing. Arrive in Gustavia, check in, and settle into the most glamorous harbor in the Caribbean.
Day 5: St. Barts - Colombier & Shell Beach
Hike or sail to Colombier Beach, swim with sea turtles, and enjoy dinner ashore. Add in Shell Beach for a daytime dip or cliff-jump.
Day 6: St. Barts > St. Martin - Simpson Bay (3.5 hrs)
Sail back to St. Martin, stopping for a swim at Tintamarre Island if you like. Return to Simpson Bay or Marigot for your final night.
Day 7: Disembark in St. Martin
Have a slow breakfast on deck before heading back to the airport. You’re leaving rested, sun-warmed, and a little more in love with the sea.
Best Time to Visit
This island trio is a year-round sailing destination, but the sweet spot is December through June, when the skies are clear, the water is warm, and the wind is just right.
• High Season (Dec–Apr): Perfect conditions and a festive atmosphere — especially New Year’s in St. Barts, which is legendary.
• Shoulder Season (May–Jun): Fewer crowds, excellent weather, and better value.
• Low Season (Jul–Nov): Hotter and riskier with storms, but possible with careful planning and travel insurance.
Why a Sailing Vacation is Ideal
You could do this trip with hotel bookings, ferry tickets, and taxis. But you’d miss the magic. A yacht gives you the freedom to explore each island on your own terms, to sleep in quiet bays, to swim before breakfast, and to toast the sunset from your own floating terrace.
No rushing, no unpacking, no schedules. Just you, the sea, and a string of stunning islands — each one more beautiful than the last.
Recommended Sailing Experience Level
This is a great route for first-time sailors, couples, or groups who want a balance of relaxation and discovery. Most sailing is line-of-sight, and while some crossings (like to St. Barts) can get choppy, it’s nothing a skippered charter can’t handle.
Style, Stillness, and a Sea Full of Possibility
This isn’t just a sailing trip. It’s a week of beautiful anchorages, barefoot afternoons, seaside rosé, and slow, golden mornings. It’s St. Martin’s flavor, Anguilla’s calm, and St. Barts’ sparkle — all from the deck of your own yacht.
Ready to Sail in Style?
Let’s plan your chic Caribbean escape. Whether you’re dreaming of boutique beaches, barefoot dinners, or designer shops with sea views — we’ll match you with the perfect boat. Reach out to Sail.Wind.Sea and get ready to set sail from St. Martin.