Hero Image

St. Martin Sailing Charter


The Windward and Leeward islands form the eastern border of the Caribbean Sea. Stretching from Grenada to Martinique, the Windwards got their name because British ships sailing from other colonies frequently had to beat the weather to reach them. The northern islands of the archipelago are more to leeward, so the British called them the Leeward Islands. They begin in Dominica, just above Martinique, and arc gently northwest for a bit under 150 miles to include Guadeloupe, Antigua, Nevis, St. Kitts, St. Barts, Anguilla, and many others. They end near St. Martin 150 miles east of Puerto Rico. These waters are an ideal location for staging a St. Martin sailing vacation to a variety of destinations throughout the Leeward chain.

Whether the island is British, Dutch, French, or independent, each has unique characteristics ranging from the upscale and trendy to the laid-back and isolated. Some islands are mountainous remnants of ancient volcanoes carpeted with lush rain forests. 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 yacht charter.

This destination is closed from September 1st to September 30th.

Image Gallery

Sailing in St. Martin

Because of the extent of the cruising ground a St. Martin yacht charter represents a diverse offering of sailing adventures. Novice and experienced sailors alike will find a charter experience ideally suited to match an individual’s level of skill and competence as a skipper. Charters with short passages and easy navigation or spirited open-water passages and negotiating reefs to drop anchor in secluded island settings are both possible in the Leeward Islands.

The trade winds typically blow from the northeast to east November through March and east to southeast 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, with average year-round temperatures holding at about 80°F (26°C).

St. Martin Highlights



Known for its beautiful beaches, numerous coves and bays, as well as its marine park, low-lying Anguilla is laid-back Caribbean charm at its best. The mix of quiet anchorages and towns with a variety of restaurants and bars has long attracted sailors. The snorkeling on the reefs where colorful tropical fish abound is excellent in many locations, and scuba diving on the seven wrecks sunk deliberately on the reef to create a thriving habitat for sea life is some of the best in the Caribbean. Dives off Sandy Island and the Prickly Pear Cays are popular. The anchorage off Crocus Bay, on the north shore of Anguilla, is protected, quiet, and beautiful.

View Anguilla highlight >

St. Martin

St. Martin

The island of St. Martin has two spellings since half of it is French (St. Martin) and the other half is Dutch (St. Maarten). More than one million visitors arrive every year to enjoy the beautiful beaches, the duty-free shopping, the hundreds of restaurants, luxury hotels, and the dozen or so casinos. For sailors the annual St. Maarten Heineken Regatta held every March and the classic yacht regatta in January are major events. The full-service marinas in Simpson Bay and Simpson Bay Lagoon (the landlocked lagoon is 12 square miles!) are always a bustle of activity, and the megayachts are everywhere, like floating palaces. Marine parks on the island offer superb swimming and snorkeling, and the beaches are fantastic.

View St. Martin highlight >

St. Barts

St. Barts

St. Barts (St. Barthemey) is a relatively small island popular for the French allure of Gustavia, the main harbor and settlement. A wide mix of chic boutiques, art galleries, and upscale restaurants line the streets of this scenic town tucked against the shore at the base of lush green hills. A short hike up to the lighthouse at Fort Gustav affords unparalleled panoramic views of the surrounding islands. The quiet, picturesque anchorage at Anse de Colombier is a secluded bay off the beaten track, promising a restful night in a beautiful setting. The white-sand beach curves along the shore, perfect for swimming and sunbathing. The bay is part of the St. Barts Marine Reserve, well known for its superlative snorkeling and scuba diving.

View St. Barts highlight >

St. Kitts

St. Kitts

St. Kitts (St. Christopher Island) is replete with astonishingly blue bays fringed with tall palms and white-sand beaches as well as excellent scuba diving on the extensive reefs. Mt. Liamuiga, a Carib word meaning fertile isle, St. Kitts’ original name, rises to 3,792 feet above sea level. The mountain is cloaked in an often cloud-shrouded rain forest, home to many plants and animals, including African vervet monkeys, which are in evidence on the many hiking trails. Once active sugarcane plantations are open for tours or have been converted to inns and restaurants well worth visiting by taxi or in a car rental. There’s also a fascinating old fort. White House Bay and Ballast Bay are lovely anchorages. Basseterre, the capital of St. Kitts, is the site of the original French settlement and has eclectic shops and a number of restaurants. The nearby island of Nevis is also an interesting stop.

View St. Kitts highlight >

Yachts & Availability

Find out which yachts are
in this destination and view available charter dates.

Check Availability

or Contact one of our vacation planners to assist in booking your charter:

by phone: 888-952-8420
by email: sales@moorings.com


As always, the Moorings provide a great sailing experience.

The moorings provide the necessary elements that make the sailing experience a trip for the…


Read full review

St. Martin to Guadaloupe -- Some Tough Sails but Worth the Work

St. Martin to Guadaloupe. Please see http://www.rtcutler.com/photos/Leeward2008.htm for photos and an account of the…


Read full review

"Catch the trade winds in your sails. Explore. Dream. Discover. Words of wisdom by Mark Twain

No strangers to sailing with Moorings, the Sims, Wrights and Agro families had been vacationing…


Read full review

Similar Cruising Areas

Tortola Sailing Charter

Tortola, Jost Van Dyke, Virgin Gorda, and Anegada are the major isles…

St. Lucia Sailing Charter

St. Lucia is sometimes called the Jewel of the Windwards, and it’s…

Phuket Sailing Charter

Nestled in the heart of Southeast Asia, Thailand is endowed with unparalleled…

Sailboat Resume

No formal certification is required for most regions. Complete our Sailboat Resume and we will immediately inform you what size yacht you qualify to sail with us and which destinations are appropriate for your experience.

Complete our Sailboat Resume



Our 2016 brochure
The Moorings 2016 Brochure
Request a brochure
View Brochure Online


Captain's Rewards

The Moorings Captain's Reward Program - Earn rewards just for sailing with us!

View program details here

Special Offers

Request the new 2016 Moorings brochure and discover unforgettable moments on the water.


Sign up for news and special offers!