St Martin Photo Gallery

The Windward and Leeward Islands form the eastern border of the Caribbean Sea, with the Windward Islands stretching from Grenada to Martinique.

The Leeward Islands begin in Dominica, just above Martinique, and arc gently northwest for under 150 miles, including Guadeloupe, Antigua, Nevis, St. Kitts, St. Barts, Anguilla, and many others. They end near St. Martin, 150 miles east of Puerto Rico. These breathtaking, turquoise waters are an ideal location for staging a St. Martin yacht charter to various destinations throughout the Leeward chain.

No matter where you visit during your St Martin sailing adventure, whether the island is British, Dutch, French, or independent, each has unique characteristics ranging from upscale and trendy to laid-back and isolated. Some islands are mountainous remnants of ancient volcanoes carpeted with lush rainforests. Others are low-lying, flat, and rimmed with incredible white-sand beaches and coral reefs teeming with sea life made to order for an unforgettable St. Martin charter vacation.

Whether you're looking for short passages and easy navigation or spirited open-water passages where you will need to negotiate reefs to drop anchor in secluded island settings, there are limitless possibilities for exploration during a sailing adventure in St Martin. 

When cruising in St Martin, the trade winds typically blow from the northeast to east from November through March and east to southeast from April through October, ranging from 10 to 25 knots. They are the power behind the north equatorial current, which usually isn't a factor except where it intensifies around the ends of some islands. Tidal currents are weak due to the slight tidal range of about 1.5 feet. 

The Leeward Islands have one of the most pleasant climates in the entire Caribbean. Average year-round temperatures are about 80°F (26°C), and rainfall totals an average of 45 inches (1143 mm) yearly.

The Easterly Trades winds are generally 10 to 20 knots, lighter in the summer months, during the hurricane season, between August and September. The stronger Christmas winds blow for a few weeks in winter and can be up to 25 to 30 knots. During these weeks, a northeast swell dominates above 8–9 ft.

Visibility is generally excellent, and on apparent days, you can see the islands of Saba, St Eustatius (Statia), St Christopher (St Kitts), and even Nevis, some 60 miles to the southeast. Fog is unheard of, but occasionally haze, especially from August to October, can reduce visibility to 15 miles. 

The Anguilla Summer Festival Carnival celebrates culture, tradition, and community spirit. Whether you're dancing in the J'ouvert parade, cheering on your favorite boat in the races, or savoring delicious local cuisine, every moment is an opportunity to connect with the vibrant spirit of Anguilla. 

J’ouvert Morning – August 3, 2026

Kick off the celebrations with J'ouvert, a parade starting at 5 AM. Revelers gather in the predawn darkness to dance, drink, and celebrate along the streets from The Valley to Sandy Ground.

August Monday Beach Party and Boat Race – August 3, 2023

After J'ouvert, the fun continues with the August Monday Beach Party at Sandy Ground. The highlight of the carnival is that this all-day event includes live music, delicious local food, and the crowd favorite August Monday Boat Race, which starts at 1 PM. The race, a festival's cornerstone, sees boats from all over the island competing in a thrilling test of skill and endurance.

ST MARTIN ITINERARY 

Day 1: 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. Of course, casual eateries also abound, as do lively bars with live entertainment. Cruising in Marigot is an excellent way to ease into a St. Martin yacht charter. 

Day 2:  The main port of entry to the British island of Anguilla, Road Bay, is one of the nicest anchorages in the northern Leewards—a beautiful white sandy beach runs along the shore, with numerous casual restaurants and bars. Laid-back and unpretentious is the rule on Anguilla, one of the chief appeals of Road Bay yachting. 

Day 3:  British island of Anguilla, Road Bay (Anguilla Carnival 2026)

Day 4:  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 plethora of watersports, kite surfing, windsurfing, kayaking, and many restaurants and boutiques, the bay also has a quieter side. If you want nude beaches and lively nightlife, it is available, however, a relaxing evening aboard in a scenic anchorage, is also a favourite. The only caveat is that Orient Bay can be rugged to enter certain conditions. At all times, careful attention is warranted.  

Day 5:  The main port of entry on St. Barts is the scenic and chic harbor of Gustavia, situated on the south side of the island near its western end. Snug and protected, this harbor is a favorite among wealthy owners of superyachts. Boutiques featuring world-famous designer wear and jewelry vie for space with superb restaurants specializing in French cuisine. However, more casual dining places are also nestled on the picturesque streets. The red roofs of many of the buildings give Gustavia a distinct character. Some sailors call it the Riviera of the Caribbean. Cruising in Gustavia waters is a highlight of any Eastern Caribbean yacht charter.  

Day 6:   Located on the shores of Great Bay, Philipsburg, the capital of Dutch St. Maarten, is a busy place with all the amenities a boater could want. Marinas, waterfront stores and restaurants, a selection of casinos, and plenty of nightlife make Great Bay cruising one of the more popular adventures on the island.   

Day 7:  Crocus Bay cruising brings you to a peaceful and secluded anchorage with cliffs rising from white-sand beaches.