A St. Martin sailing itinerary is one of the best ways to experience the northeastern Caribbean. With short sailing passages, protected anchorages, world-class restaurants, and crystal-clear waters, St. Martin, St. Barths, and Anguilla are ideal destinations for both first-time charter guests and experienced sailors.
This 9 night itinerary begins and ends in Marigot, taking you to the gourmet village of Grand Case, the unspoiled island of Tintamarre, the luxury harbor of Gustavia, the secluded beauty of Colombier Bay, and the spectacular beaches of Anguilla. Most sailing days are under three hours, leaving plenty of time for swimming, snorkeling, paddle boarding, and relaxing ashore.
Day 1: Marigot to Grand Case
Distance: 7 nautical miles
Sailing Time: About 1 hour
Begin your St. Martin yacht charter with an easy sail along St. Martin’s northern coastline to Grand Case, often called the culinary capital of the Caribbean.
After anchoring, spend the afternoon swimming or relaxing on the beach before heading ashore for dinner.
Where to Eat
- Rainbow Café
- Ocean 82
- Le Cottage
- Grand Case Lolos for authentic Caribbean barbecue
- Java restaurant
Provisioning
- Carrefour Market (Formerly Le Grand Marche)
- Cost-U-Less
- Super-U
Before departing Marigot, take advantage of St. Martin’s local markets. In addition to supermarkets, L’Épicerie de Marie offers gourmet cheeses, fresh produce, seafood, and French specialty foods, while Market Garden Cupecoy is ideal for organic, vegan, and specialty groceries.
If your St. Martin bareboat charter begins on a Wednesday or Saturday, visit the Marigot Waterfront Market for fresh tropical fruit, local spices, and seafood sold directly by local fishermen. It’s a great place to pick up fresh ingredients before setting sail.
Day 2: Grand Case to Tintamarre
Distance: 8 nautical miles
Sailing Time: About 1 hour
Tintamarre lies within the St. Martin Nature Reserve and is one of the most beautiful anchorages in the region. The island is uninhabited, making it perfect for a peaceful overnight stay surrounded by nature.
The calm waters are ideal for snorkeling with sea turtles, paddle boarding, or enjoying a quiet beach picnic. A short walk inland leads to the island’s abandoned airstrip, offering a glimpse into its history.
Activities
- Snorkel with sea turtles
- Paddle board
- Beach picnic
- Walk to the abandoned airstrip
There are no restaurants or shops, so plan to enjoy meals aboard and bring plenty of food and drinking water before arriving.
Day 3: Tintamarre to Gustavia, St. Barths
Distance: 18 nautical miles
Sailing Time: About 2 hours 15 minutes
Today’s sail takes you to the glamorous island of St. Barths. Gustavia is famous for its picturesque harbor, luxury boutiques, French cafés, and vibrant waterfront lined with superyachts.
Spend the afternoon exploring the town before enjoying dinner at one of the island’s renowned restaurants.
Recommended Restaurants
- Bonito
- Eddy’s Ghetto
- Le Select
- Shellona
Great Places to Visit
- Shell Beach
- Gustavia Harbor
- Luxury boutiques
- Historic waterfront
Gustavia is also an excellent place to restock fresh produce, gourmet groceries, wine, and bakery items.
Day 4: Explore Gustavia
Take a break from sailing and spend the day discovering one of the Caribbean’s most exclusive destinations.
Relax at Gouverneur Beach, browse designer boutiques, enjoy lunch at a beach club, or simply watch the impressive collection of superyachts in the harbor.
Recommended dinner options include Bonito, Shellona, or L’Isola.
Day 5: Gustavia to Colombier Bay
Distance: 5 nautical miles
Sailing Time: Around 40 minutes
A short sail brings you to Colombier Bay, one of St. Barths’ most secluded anchorages.
Accessible only by boat or hiking trail, Colombier offers crystal-clear water, excellent snorkeling, and peaceful surroundings away from the crowds.
Activities
- Snorkeling
- Paddle boarding
- Swimming
- Short coastal hike
Arrive early during peak season, as moorings and anchoring space can fill quickly.
Dinner is best enjoyed aboard while watching the sunset over the bay.
Day 6: Colombier Bay to Île Fourchue to Road Bay, Anguilla
Distance: 23 nautical miles
Sailing Time: About 2 hours 50 minutes
Begin the morning with a stop at remote Île Fourchue, one of the Caribbean’s hidden snorkeling gems. The island’s clear waters are home to colorful reef fish and healthy coral.
Continue north to Road Bay in Anguilla, where you’ll complete customs clearance before settling into the island’s relaxed atmosphere.
Restaurants
- Elvis’ Beach Bar
- SandBar
- Lit Lounge
Road Bay offers small grocery stores, ice, and basic supplies if you need to restock before continuing your journey.
Day 7: Enjoy Anguilla
Spend a full day exploring Anguilla’s spectacular beaches, often ranked among the best in the Caribbean.
Popular stops include Shoal Bay and Meads Bay, where soft white sand meets calm turquoise water.
Suggested Activities
- Beach hopping
- Paddle boarding
- Snorkeling
- Swimming
Recommended restaurants include Blanchards, Straw Hat, Jacala, and Sharky’s.
Day 8: Road Bay to Prickly Pear Cays to Rendezvous Bay
Distance: 12 nautical miles
Sailing Time: Around 1 hour 30 minutes
Leave early to enjoy excellent snorkeling around the Prickly Pear Cays before excursion boats arrive.
Continue to peaceful Rendezvous Bay for an afternoon of swimming, paddle boarding, and relaxing on one of Anguilla’s longest beaches.
If conditions allow, enjoy dinner at the famous Sunshine Shack.
Day 9: Rendezvous Bay to Simpson Bay
Distance: 15 nautical miles
Sailing Time: About 1 hour 50 minutes
Return to St. Martin for your final evening aboard.
Simpson Bay offers lively restaurants, marinas, beach bars, and convenient provisioning before your charter ends.
Recommended Restaurants
- SkipJack’s Seafood Grill
- Sandbar SXM
- Greenhouse
- Buccaneer Beach Bar
- Sale & Pepe
This is the perfect place to celebrate your final night with a waterfront dinner while reflecting on an unforgettable Caribbean adventure.
Day 10: Simpson Bay to Marigot
Distance: 3 nautical miles
Sailing Time: About 20 minutes
Enjoy breakfast aboard before making the short sail back to Marina Fort Louis for check-out.
Allow plenty of time for fueling, packing, and completing your charter return.
Planning Tips
To make the most of your St. Martin sailing itinerary:
- Complete your main provisioning before leaving Marigot.
- Carry passports for customs when visiting St. Barths and Anguilla.
- Reserve popular restaurants in Grand Case and Gustavia during peak season.
- Keep snorkeling gear easily accessible for Tintamarre, Colombier Bay, Île Fourchue, and Prickly Pear Cays.
- Check weather forecasts before longer crossings, particularly between islands.
Best Time to Sail St. Martin
The ideal sailing season runs from December through May, when steady trade winds, warm temperatures, and lower rainfall create excellent cruising conditions. June through November is hurricane season, so weather should be monitored closely if traveling during these months.
Frequently Asked Questions
Is 10 days enough to sail around St. Martin?
Yes. Ten days allows you to explore St. Martin, St. Barths, and Anguilla comfortably while keeping most sailing passages short.
Do I need customs clearance?
Yes. When visiting both St. Barths and Anguilla, you should complete customs and immigration procedures according to local regulations.
Can beginners follow this itinerary?
With an experienced skipper or a crewed charter, this route is suitable for sailors of all experience levels thanks to its relatively short passages.
What are the best snorkeling spots?
Tintamarre, Colombier Bay, Île Fourchue, and Prickly Pear Cays are widely regarded as some of the best snorkeling locations on this itinerary.
Where should I provision?
Marigot and Gustavia offer the widest selection of supermarkets, bakeries, wine merchants, and marine supplies.
Why Choose This St. Martin Sailing Itinerary?
This 9 night sailing route combines everything that makes a St. Martin vacation unforgettable. You’ll enjoy gourmet dining in Grand Case, snorkel with sea turtles at Tintamarre, explore the elegant harbor of Gustavia, relax in the peaceful surroundings of Colombier Bay, and discover Anguilla’s world-famous white-sand beaches.
With mostly short sailing days, beautiful anchorages, and plenty of opportunities to swim, paddle board, snorkel, and dine ashore, this sailing itinerary is ideal for families, couples, and groups looking to experience the very best of St. Martin, St. Barths, and Anguilla in one unforgettable yacht charter.
