St. Martin Sailing Itinerary

St. Martin Sailing Itinerary

Take Your Dream Holiday to St. Martin 

Known for its colorful marriage between European and Caribbean culture, St. Martin is an island with a split personality. Known as the culinary capital of the Caribbean, the island of St. Martin is part of the Leeward Islands, which can be found in the northeastern Caribbean Sea.  The island is particularly unique as it is divided between two countries. The north side, known as Saint Martin, is a collectivity of France in the West Indies, and the southern side, known as Sint Maarten, is owned by the Kingdom of the Netherlands in the Caribbean. The Dutch side is known for its nightlife, beaches, jewelry, and drinks made with native rum-based guavaberry liquors. In contrast, the French side is perfect for anyone looking for some shopping therapy, beaches, and French-Caribbean fusion cuisine. 

Another key draw of St. Martin is its proximity to other Caribbean islands, including Anguilla, Saba, Nevis, St. Kitts, and St. Barts. St. Martins is one of the most popular sailing destinations in the Caribbean, primarily because of the variety of things you can do within the region. In one day, you can go scuba diving with nurse sharks, try your luck at a casino, eat world-class cuisine and even fit in some duty-free shopping before heading out for some drinks and dancing. Yachting in and around St. Martin offers remote, unspoiled anchorages, secluded Caribbean coves, stunning beaches, and fantastic coral reefs. This region provides the perfect combination of chic European sophistication and a laid-back Caribbean charm. All in all, St. Martin is the ideal place to charter a yacht. 

Are you ready to begin your yacht experience in St. Martin? Let’s go.


Day 1: Our crew will be happy to coordinate a taxi pick-up once you arrive at the international airport on the Dutch side of St. Maarten. Our driver will meet you at baggage claim and take you to meet the crew at the marina. Once aboard the boat, you will be briefed before allowing to settle in and enjoy your welcome cocktail on board. 

We will then set sail six nautical miles from Dutch St. Martin to Anguilla, a British territory known as one of the most beautiful islands in the Caribbean. On our way to Anguilla, we will stop by smaller islands such as Prickly Pear Cays to enjoy lunch and a quick swim. We will drop anchor in Road Bay, the main port of Anguilla. In the afternoon, guests are welcome to explore the island's art galleries, tour historic sites and museums or spend their day relaxing on the beach. 

For dinner, head on over to Gorgeous Scilly Cay for a lobster dish that can be washed down with a Pyrat Rum, a local specialty, aged in oak barrels. And if you aren’t quite ready to go to bed just yet, you can head on over to one of the late bars at Sandy Ground for a cocktail or two before heading in for the night. 

Day 2: It’s time to sail back to St. Martin, but this time we are heading on over to the French side, specifically the French capital, Marigot. Here, guests can visit the town’s many restaurants, pastry shops, luxury boutiques, and even do some duty-free shopping. If time permits, a visit to Fort Louis is a must. Not only was the fort built in 1767, but it also offers stunning views across Marigot Harbour and the hills above the Bellevue. You can even see the silhouette of Anguilla island in the distance if the skies are clear enough.  

For dinner, guests can choose to either stay in Marigot or head on over to Grand Case, a historic seaside and fishing town known for its excellent restaurants that serve delicious french-Caribbean cuisine. 

Day 3: In the morning, we will set sail to the island of Tintamarre, off the tip of French St. Martin, where guests can go snorkeling in the protected marine preserve. This small uninhabited island is home to two beautiful scuba diving sites and some secluded beaches. 

We'll set sail toward Orient Bay in the afternoon, where we will anchor for the night. Orient Bay is St. Martin’s most famous beach and is known as quite the party hotspot. The bay is surrounded by a two-mile-long white sand beach and protected by a reef, making it the perfect spot for water sports. Spend the afternoon snorkeling, parasailing, kitesurfing, jet skiing, or even just lounging lazily on the beach. 

For dinner, choose to dine ashore or enjoy a delicious barbecue on board before heading in for the night. 

Day 4: It’s time to visit the peaceful island of Ile Fourchue, off the coast of St. Barts. Once moored, grab your snorkeling gear and make sure to keep a watch out for any sea turtles. If time permits, we can also climb to one of Fourche’s five peaks to enjoy the panoramic view of the Leeward Islands. 

Lunch will be served on board as we head over to our final destination for the day in St Barts. We will anchor in the glamorous harbor at Gustavia, on St. Bart’s east coast. Guests are highly encouraged to take a short walk to Shell Beach to look for some unique-looking shells before grabbing a light snack at one of the beachside restaurants. 

In the late afternoon, snorkel the wreck of the motor yacht, “Nonstop,” head ashore and explore the town’s exclusive boutiques or rent a scooter and drive around to some of the island’s more isolated beaches. For dinner, make sure to linger around town as the nightlife in St. Barts is genuinely a one-of-a-kind experience. 

Day 5: It’s time to head back to paradise. We will cruise from Gustavia along St. Barts coast to the beautiful turquoise waters of Anse de Colombier. If you are looking to spot a turtle, this is the perfect place. Not only is the water teaming with sea life, but it is so clear that you can see right to the bottom. 

In the afternoon, we will leave the hustle and bustle of St. Bart’s behind to visit Saba, an island so untouched that it is magical. Saba is small but mighty. Although it has a footprint of less than 5 square miles, it is filled to the brim with stunning scenery, including lush greenery, towering cliffs, and a dormant volcano. Known as the “Unspoiled Queen” of the Caribbean, the beaches are not the main draw on Saba. Instead, visitors can choose to climb, hike, or scuba dive. The island is home to many coral formations and sea life, including dolphins, sharks, and turtles. However, it is also known for its underwater mountains created by volcanic activity. With no hotels, beaches, or ports, Saba is one of the Caribbean's best-kept secrets. 

In the evening, you can choose to stay on the island for dinner or head back to the boat to enjoy a diclinous chef-cooked meal on board underneath the stars. 

Day 6: It’s time to go to St. Kitts and Nevis for some more relaxation and beach time. We’ll anchor for the night around Pinneys Beach, a rarely crowded gorgeous stretch of white sand where you can grab your snorkeling gear and take another dip or two in the ocean. 

Today is all about lying n the sun, exploring the island’s many beaches, and eating delicious food before we head on over to Antigua. 

Day 7: Antigua is calling your name. Famous for its warm, steady winds, remarkable beaches, and epic yachting events, Antigua is home to over 365 beaches, one for every day of the year. 

We’ll spend the day exploring the island’s many caves, coves, and beaches. We’ll explore Carlisle Bay, a palm-lined beach, and enjoy a leisurely lunch on board before setting sail again towards Cades reef. Once anchored, guests are welcome to jump into the warm Caribbean waters and explore this reef, which is known as one of Antigua’s most beautiful snorkeling sites, before heading to another one of Antigua’s 365 beaches. We’d recommend snorkeling or diving at Ledges or Cow and Calf. 

Once you are all “beached out” for the day, we’ll head on to the main town for some shopping, dinner, and cocktails. If you are craving some pizza, we can also head over to Pizza Pi, known for having the best pie in the Caribbean. The unique twist is that this restaurant is only accessible by boat. Is there anything better than eating pizza as you snorkel?

Day 8: It’s time to head back to St. Martin. Enjoy one last trip on board as we make our way back to the marina. Take the time to soak in all of the island’s magic before disembarking and bidding the crew goodbye. Until next time!

*Remember that we are here to help you plan your dream vacation, so the itinerary outlined above can be changed. All you need to do is discuss your needs with our crew, and we will do our best to make it happen. Do you want to stay one day longer for a particular bay or move on to a new experience? No problem, we are here to make your visit to St Martin unforgettable.