It’s the smallest landmass in the world shared by two independent countries— boasting two clearly separate sides: French St. Martin in the north and Dutch St. Maarten in the south. This distinction makes the Leeward Island a delightful combination of sophistication and relaxation, enjoyed by diverse groups of vacationers and sailors.
With sunny, 80 °F weather being the region’s norm, it’s a rather popular getaway. Compared to some other island escapes, Saint Martin’s offers some ports and surrounding villages that are extremely developed, offering dining, shopping and entertainment beyond the waters. Anchor at the chic harbours of St. Barts or St. Kitts and the incredible beaches of Anguilla.
St. Martin and the Leeward Islands are a sailor’s Caribbean dream— a destination for bareboaters and crewed yacht charters alike. Many of the islands are dotted far enough apart to enjoy scenic three or four-hour sails, while others are close enough for same-day excursions. Explore all this romantic destination has to offer, whether you choose to hit the sea solo or book an all-inclusive sailing vacation.
There’s a reason celebrities escape to stunning St. Martin and its surrounding islands for their luxurious getaways. This Leeward Island and close neighboring islands— Anguilla and St. Barths— offer lush palm-swaying beaches and miles upon miles of striking blue waters to explore, plus high-end shopping and irresistible French plates. Perfect your balance on a paddleboard or build a grand sandcastle on the white sand. With a number of lively events and thrilling activities for those of all ages, the whole family is sure to fall in love with these sailing grounds on your St. Martin yacht charter.
Grand Case. Nestled west on the French northern side of St. Martin lies the vibrant Grand Case cove. The Baie de Grand Case boasts clear blue waters and wonderful Caribbean snorkeling and diving. This corner of paradise is best known for is its excellent French and Creole cuisine. Feast like kings and queens at one of the many fine dining restaurants at “The Gourmet Capital of the Caribbean,” like the Bistrot Caraibes or La Villa. Then, sail to the reef at Créole Rock to watch the sunset at one of the best spots to bid the evening adieu.
Tintamarre Island. Venture off the traditional sail-streaked path to the peaceful, uninhabited Île Tintamarre. This 80 acre island holds the remnants of its previous life— once the home of a booming cotton plantation. Stepping onto its land, you’ll catch a glimpse of its abandoned railroad track, airstrip and the ruins of buildings and stone walls. Spend a few hours exploring traces of its history or float in its serene lagoon. Tintamarre’s cove is home to sea turtles, stingrays and an abundance of fish, who all enjoy its private seclusion, and is a quiet fisherman’s delight. Read more on Tintamarre’s fascinating history here.
Anguilla. Travel across the Anguillan Channel to the island of Anguilla, a hot spot for its incredible beaches, bays and overwhelming luxury. It’s about a three hour sail from Marigot across clear line-of-sight waters, boasting a few favorite anchorages— like Sandy Ground, known for its renowned beach bars such as Elvis Beach Bar and the Sandbar— or one of its world-class, protected snorkeling areas. Anguilla’s robust reef system and reputation for shipwrecks makes it a diver’s paradise too, coined the “Wreck Dive Capital of the Caribbean.” Shop. Dine. Swim. A full island of adventure awaits.
Annual events in St. Martin often celebrate the region’s cultural heritage with lively music, delicious ethnic food and interactive land and water activities. In fact, St. Martin hosts one of the most well known sailing races: the Heineken Regatta. Depending on the month you visit, you can join in on unique competitions, dance shows, parades and more. Enjoy the French Caribbean like a local. Mark your calendars, early, to get in on the exotic fun!
Pool Party Loterie Farm
International Female Tennis Tournament
Pool Party Loterie Farm
St. Martin Carnival
Arrow Root Jollification
SXM Music Festival
DP Dance Salsa Festival
Dutch Side Carnival
Endemic Animal Festival
Saint Louis & Rambaud Fête
Festival of the Sea
World Music Day
Laugh till Belly Burst XV
Grand Case Fête
Sandy Ground Village
SXM Best Weekend
World Tourism Day
Body Building Tournament
Caribbean Tourism Day
Tourism Caribbean Month
Saint Martin’s Day
Saint Martin Christmas
Grand Case Lighting Parade
Enjoy that wonderful Lesser Antilles weather on your St. Martin yacht charter, no matter when you set sail. The island and surrounding regions in the Caribbean experience temperatures averaging 80°F and are kissed by breezy, cool trade winds year round— which helps to cut the heat.
While vacationers visit this Leeward Island every month of the year, December through April is typically the best time for sailing. December in particular is a coveted St. Martin vacation month, usually the best time for refreshing winds. Fog is nearly unheard of here, and visibility is usually crystal clear during this island’s most heavily traveled period.
June begins the region’s hurricane season, and rain showers are more common from summer throughout October. While some charters still enjoy cruising the waters during this time, conditions aren’t always ideal. Book your charter ahead of time to hit the Caribbean when cruising conditions are just right.
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Start your St. Martin sailing holiday Marina Fort Luis in Marigot. Located 20 minutes from the airport and surrounded by many great restaurants and shopping, this is the ideal place to start your sail. Marigot is the capital of the French side of St. Martin. The waterfront is attractive, the shops and boutiques plentiful, and the selection of restaurants varied and known for quality French cuisine. Don’t forget to visit Fort Louis and explore the beautiful grounds.
1 hours | 4 miles
Head north along the island’s gorgeous coastline to Grand Case, the gourmet capital of the Caribbean. Indulge in a decadent French or Creole-inspired meal, Enjoy a swim and a local lunch at the “Lolo’s”. Take the dinghy and go to Creole Rock for some nice snorkeling. Grand Case is a small village with her large bay with crystal clear water and a long beach. Cap off the day with a sip of local rum as you watch the sun set on the horizon.
0 hours | 0 miles
Friar’s Bay is quiet and family friendly. Here the gently rolling waves of the bay are warm and filled with colorful fish, while the bright white strip of sand is fringed with quietly swaying palms.
2 hours | 8 miles
Situated on the northeast coast of French St. Martin, yachting in Orient Bay is popular among sailors cruising the northern Leeward Islands. Aside from its beautiful white sandy beach and the abundance of water sports, kite surfing, windsurfing, & more. It offers many restaurants and boutiques. Enjoy dancing to live music or relax on a sun lounger. Orient Bay has something for everyone. There is however, no moorings on the Bay, but there are two good anchorages; Ile Pinel and Green Cay.
3 hours | 16 miles
Cruise north from Gustavia along St. Barts’ coast to the turquoise waters of Anse de Colombier. The shallow well protected reefs around the area are perfect for snorkeling with turtles, dolphins, and other tropical fish. On the southern hill is a house built by the Rockefeller family, which once owned Anse de Colombier. Now it’s part of the St. Barts Marine Reserve. When you go chartering in Anse de Colombier, you’re sure to find the beauty and charm of the Eastern Caribbean.
1 hours | 4 miles
Point your bow toward Saint-Barthélemy Channel and enjoy a few hours of blue water sailing. Anchor at glamorous Gustavia, on St. Barts’ east coast, and head ashore for the chic French atmosphere and delectable cuisine. Explore the 17th century forts that line the harbor, from Fort Karl on the north to the lighthouse and cannons of Fort Gustaf in the south. Near Fort Gustaf is Shell Beach, a popular spot for beachcombers seeking beautiful seashells. The red roofs of many of the buildings give Gustavia a distinct character. Some sailors call it the Riviera of the Caribbean. Chartering in Gustavia waters is a highlight of any Eastern Caribbean yacht charter.
4 hours | 20 miles
Maho Beach is a small stretch of white beach. It is the location that attracts all of its visitors: The beach is located at the Western end of the runway of Princess Juliana International Airport, thus providing you with a very special experience! For those who love the thrill, or just like airplanes, watch and see incoming jets gliding in and landing just a few yards above your head! Maho Beach is facing the west of the Caribbean sea, so sunset views are great The best time of the day to see the most is between 1:30pm – 5:00pm.
1 hours | 6 miles
Next stop is Philipsburg, St. Martin’s lively Dutch capital. This exciting town has it all, from chic boutiques, vibrant nightlife, and a sophisticated atmosphere. This town, famous for shopping you will find everything on this mile-long street lined with palm trees inviting you to take a peek inside the designer stores and fun and whimsical local shops.
2.5 hours | 12 miles
A great stop to start out your fifth day is the island of Tintamarre. Taking a walk around this now uninhabited island, you will find the remains of an airstrip, a small rail track and a cotton plantation. The most accessible bay and best place for swimming is “Baie Blanche”, is situated on the west coast facing Saint Martin. The beach is pristine and almost fully protected, so the water color is gorgeous! There’s no restaurant on this island but you will find wood tables under the trees! This is the ideal place for the picnic lovers.
2.5 hours | 12 miles
Start your fifth day charter and head to West End Village, in Anguilla. Visit the stunning natural rock and limestone arch in West End for a great photo opportunity. This island is known as the wreck diving capital of the Caribbean, with seven sunken wrecks home to colorful fish and corals that are perfect for snorkeling and scuba diving.
2 hours | 10 miles
Road Bay, is one of the nicest and most popular anchorages in the Leeward Islands. A beautiful white sandy beach runs along the shore, where you’ll find numerous casual restaurants and bars. Mingle with the locals at Johnos’ bar and enjoy the live jazz music and see the locally made sailboats on the beach getting ready for the next regatta. Sailing is the national sport of Anguilla.
1.5 hours | 6 miles
Set a course for the Prickly Pear Cay, located six miles north of Road Bay. The small pair of uninhabited islands is divided by a channel. Once you pass through the passage between the two cays, on the north side you will discover the long, beautiful white sand beaches with clear turquoise waters for the ideal snorkeling location. In addition to snorkeling and hiking, visitors can bird watch as well, which is a highlight of this picture- perfect destination, the birds are plentiful and will eat sugar right out of your hand.
1 hours | 6 miles
Little Bay is tiny cove, isolated and sheltered by a tight embrace of towering cliffs. If you’re feeling a little more daring, climb down the cliff or kayak or paddleboard over to this oasis. For one of the best beach experiences, travelers suggest you sneak away to Little Bay, All who visit particularly enjoy snorkeling and swimming in the aquamarine water there, especially in the late afternoon as the sun sets.
3 hours | 17 miles
The last day of your charter brings you to Happy Bay. This Bay lies to the Northwest of the island, between Friars Bay and the Bay of Grand Case. Happy Bay is still a rather unknown, almost undiscovered beach of St. Martin. This quiet beach is like a post card perfect tropical dream beach! It is the right spot for romantic beach lovers, for snorkelers, and also for sun bathers.
0.5 hours | 3 miles
Time to head back to the base. Take in your last sunrise on deck while enjoying your perfect morning cup of coffee or juice. Once you arrive relax in the warm Caribbean sun and enjoy your last day of charter before arriving at Marina Fort Louis. Enjoy a cocktail or fresh seafood for your final Caribbean lunch while you start planning your next yachting vacation.
Traveling to St. Martin is a lot easier than you might think. Most sailors fly right into Princess Juliana International Airport (SXM), flying with Delta, American Airlines, Spirit, United or other popular U.S. airlines. From the airport, it’s a short taxi ride to one of the main marinas, where you’ll board the yacht to start your charter. With such a close proximity from your arrival to your sail, there’s less waiting and more exploring on this trip.
Our team at VI Sailing can also recommend lodging and land excursions, should you want to extend your vacation, as well as to provide options for trip insurance for your Saint Martin yacht charter.