Down Island

Leeward Islands

Anguilla – Barbuda – Antigua – St. Bart’s – St. Martin/Sint Maarten – Dominica – Guadeloupe – St Kitts – Nevis – Saba – Montserrat – Sint Eustatius

The Leeward Islands begin approximately 100 miles east of the US and British Virgin Islands. They constitute the northern section of the Lesser Antilles chain of islands.

The Leeward Islands are diverse. From the charming Lilliputian-like, beach-less island of Saba, to Barbuda’s flat coral landscape with its endless pink and white sand beaches. Every island has something unique to offer.

Antigua claims 365 beaches, one for each day of the year, as well as an excellent and relaxed nightlife courtesy of its large sailing and expatriate population. St. Barth’s, 30 miles north of Antigua, offers more good food and nightlife and similar nautical themes, only on a bigger scale. You can sip champagne waterside while watching for celebrities, admire the mega yachts coming into dock, or peruse the high-end shops surrounding the harbor. St.Barth’s is akin to the French Riviera 20 to 30 years ago.

St. Martin and Sint Maarten comprise the smallest sea island in the world divided by two nations. Dutch Sint Maarten in the south and French St. Martin in the north. Together they offer twice the culture and history. Sint Maarten is more commercial than the French side and contributes shopping and tourism whereas St. Martin offers resorts, high fashion and fine dining. In Oyster Bay on the eastern side of the island you can actually be considered standing in France and the Netherlands at the same time.

If all the eating and drinking and shopping in St. Barth’s, Antigua and St. Marten wears you down, try Dominica, “The Nature Island.” Two thirds of which is covered in tropical forest; home to 1200 plant species, 365 rivers, the world’s second largest boiling lake and the Eastern Caribbean’s first UNESCO world heritage site – The Morne Trois Pitons National Park.

Looking for scenery? The southern Leeward Islands are known as “The Islands That Brush the Clouds”. They comprise: Montserrat, St. Kitts, Statia, Nevis and Saba. Sailing from the north you’ll first notice their volcanic peaks piercing white clouds and if you are lucky you’ll witness smoke and ash spitting from Montserrat’s still active volcano. Christopher Columbus named Nevis, “Our Lady of the Snows,” because from his yacht, in 1498, the clouds on Nevis’ peak appeared to dripping down its slopes. Nevis is beautiful and offers rainforests filled with playful monkeys, sugar mill ruins and more white sand beaches. St. Kitts is often termed “The Historical Capital of the Caribbean”, and offers a botanical garden; a batik factory, where artists use ancient techniques to create beautifully distinctive and colorful fabrics; and Brimstone Hill Fortress – one of the best preserved historical fortifications in the Americas.

The Leeward Islands boast a diversity of history and culture all within a few neighboring islands.

Windward Islands

Martinique – Saint Lucia – Saint Vincent – Grenadines – Grenada

The Windward Islands constitute the southeastern section of the Lesser Antilles chain of islands. They are termed the Windward Islands because they are more windward to ships transiting to the Caribbean (or the Americas) from the old world than are the Leeward Islands. Windward island sailing can be considered a mix of Virgin Island sailing and Leeward Island sailing, depending on your itinerary. You could spend your whole trip in the Grenadines alone, cay hopping and gunk-holing, much like the BVI, or, enjoy lengthy day sails in attempt to see all of the islands, from Martinique to Grenada. The Windward Islands, because of their north/south orientation allow the cruising yachtsmen perfect beam-on sailing.

Martinique is the Caribbean island with French flair and is often regarded as the “Rum Capital of the World”. St. Lucia’s Anse des Pitons might take top prize as the most spectacular and breathtaking anchorage in the world, with twin peaks towering 2,000 feet above the ocean. Bequia, known as “The Big Little Island”, is quaint and charming, exactly what you would hope and imagine a Caribbean island to be. South from Bequia you’ll find St. Vincent and the beginning of the Grenadines.

The Grenadines comprise some 32 islands and cays and stretch roughly 80 miles from St. Vincent to Union Island. Only 9 of the 32 islands and cays are inhabited, including the stunning Tobago Cays, Carriacou’s Sandy Island, Mopion, White Island and Mabouya. The Tobago Cays are a group of five small deserted islands protected from the vast Atlantic Ocean by Horseshoe Reef. Anchoring in the white sand, ocean-side in the Tobago Cays is a remarkable sensation, as there is nothing between you and the Eastern Hemisphere except a thin line of shallow coral reef. The water is remarkably clear and the reef provides hours of world-renowned snorkeling and diving. The Tobago Cays should not be missed.

From Union Island in the Grenadines it is a comfortable day’s run south to Grenada, a remarkable cruising ground by any standard. St. George’s is an excellent shopping and provisioning town, and the public market on Wednesdays and Saturdays is a unique experience. The southwestern coast of Grenada is a gunk-holer’s paradise with several sheltered anchorages.

The Windward Islands remain unspoiled and offer cruising sailboats an authentic Caribbean experience — diversion and diversity above and below the sea.