The Leeward Islands in the Eastern Caribbean span an arc of approximately 200 nautical miles. Whether you pronounce them “lee-werd” or “loo-ard”, it doesn’t matter, as both are correct. The Leewards played a major role in European colonial expansion in the New World in the 17th and 18th centuries. It also served as a theater to play out the machinations of the Spanish, French and English monarchies in their quests for control of Europe.

St. Eustatius, under Dutch control, maintained neutrality and in 1756 announced it was a free port with no customs duties. That helped trigger tremendous growth for Statia (the island’s nickname) as the major trading port of the West Indies during that era. It was so successful that it was dubbed the “The Golden Rock”.

St. Kitts became the first British Caribbean colony in 1623, and developed the model for the English sugar plantation system and the triangular trade. Sugar cane was harvested and processed by African slaves on St. Kitts into sugar loafs. The sugar loafs were shipped to England for the tables of British households. Manufactured goods from England, such as textiles and rum were sailed to Africa in exchange for slaves. The slaves were sent on ships to St. Kitts to work on the sugar plantations. The French, Spanish, Portuguese and Danish New World colonies all followed this lucrative, but harsh, system.

Antigua was home to Great Britain’s main naval station on the Caribbean in the last half of the 1700s and England’s favorite naval hero, Lord Nelson, was stationed there in 1784.

Isles des Saintes served as the backdrop for the most famous naval engagement in the Caribbean in 1782, the Battle of the Saintes. The British fleet roundly defeated the French fleet using the pioneering tactic of “breaking the line”.

By sailing the Leeward Islands, modern day cruisers have the opportunity to visit islands that have the flavor of Dutch, English and French cultures, as well as the only settlement of Carib Indians in the West Indies.

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  1. - Estimated Mileage: 0

    Road Bay Anguilla

    anchorage

    HIGHLIGHTS

    Overnight Stop: Anchor in Road Bay. Take a taxi tour of the island and visit the exclusive five star resorts on the island. Lunch at Cap Juluca and dinner at Malliouhana resorts are a must.

  2. - Estimated Mileage: 7

    Prickly Pear Cays Anguilla

    anchorage

    HIGHLIGHTS

    Lunch Stop: Pick up a mooring ball at Prickly Pear Cays. Swimming and snorkeling are good here, and scuba diving can be excellent.

  3. - Estimated Mileage: 24

    Anse Marcel Marina

    ,

    HIGHLIGHTS

    Overnight Stop: Explore the French side of this dual nationality island. Take a taxi ride to Grand Case for dinner with the street food vendors. The local baby back ribs are not to be missed.

  4. - Estimated Mileage: 13

    Simpson Bay Marina

    Simpson Bay,

    011-599-544-2309

    HIGHLIGHTS

    Overnight Stop: Dock on the Dutch side of Simpson Bay Lagoon, but dinghy over to Marigot on the French side. Marigot was location for the 1997 cruise ship disaster movie “Speed 2”. Today, it is the best location on the island for nightlife with an active restaurant and bar scene.

  5. - Estimated Mileage: 15

    Ile Fourche

    anchorage

    HIGHLIGHTS

    Lunch Stop: Pick up a mooring ball in the bay at Ile Fourche on the passage from Sint Maarten to St. Barth. The desolate island is inhabited only by goats. A great location for a swim before an al fresco lunch on board.

  6. - Estimated Mileage: 5

    Port de Gustavia

    Saint Barth'lemy - French West Indies, Saint Barths

    011-59-059-027-6697

    HIGHLIGHTS

    Overnight Stop: The Port of Gustavia offers four different options for securing a yacht overnight, depending on the size of the vessel and availability. Megayachts and superyachts can dock stern to on the quay across from the Port Captain’s office. Smaller boats can dock stern to on the quay across the harbor along Rue de la Presque’ile. There is a mooring field in the harbor with bow and stern mooring balls that tends to be full most of the time. The final option is anchoring outside the harbor off the point of Fort Oscar. While in St. Barth’s explore the beaches at Anse du Gouverneur and Anse de Grande Saline. There are a number of nude and clothing optional beaches. If that’s of interest, check with the locals for their location. Fine dining restaurants abound in Gustavia, as well as after-hours nightclubs. If you like to dance until sunrise, and hit the beach at noon, check with the locals for the current club of the moment.

  7. - Estimated Mileage: 29

    Ladder Bay

    anchorage

    HIGHLIGHTS

    Overnight Stop: Pick up a mooring ball in these adjacent bays on the northwest coast of Saba. The waters around the island are a protected marine national park with excellent scuba diving. Go ashore and take a full taxi tour of the island. Visit the villages of Bottom and Windwardside for lunch, do buy some handmade local lace and take a hike up to the top of Mt. Scenery into the clouds.

  8. - Estimated Mileage: 20

    Oranje Baai

    anchorage

    HIGHLIGHTS

    Overnight Stop: Anchor off Oranjestad behind the new breakwater. Dinghy ashore and walk up the hill on the cobblestone Old Slave Road. The village of Oranjestad is lush, green and bursting with flowers amid its gingerbread buildings.  Visit the original 1755 Dutch Reformed Church, the partially restored 1738 synagogue, the museum, and old Fort Oranje. From this fort, Statia granted the first international recognition of the new United States of America, when it fired a cannon salute to the American brig Andrew Doria anchored in Oranje Baai on November 16,1776.  A day hike to up to the extinct volcano and down into Quill Crater is great exercise.

  9. - Estimated Mileage: 20

    Port Zante Marina

    ,

    HIGHLIGHTS

    Overnight Stop: Dock at this marina next to the cruise ship port. Take a taxi tour of the island and make at least three stops: Brimstone Hill, the restored British fort known as the “Gibraltar of the West Indies”, Caribelle Batik at Romney Manor, and a drive through the undeveloped areas of the island to spot St. Kitts’ green vervet monkeys in the wild.

  10. - Estimated Mileage: 20

    Pinneys Beach

    anchorage

    HIGHLIGHTS

    Overnight Stop: Anchor off Pinney’s Beach near the Four Season’s Resort. Dinghy on to the beach and walk up to the resort’s pool bar and enjoy a cocktail while watching the sun set behind your yacht. Dinghy ashore to the capital, Charlestown and spend the day exploring this picturesque town. Charlestown was the birthplace and boyhood home of Alexander Hamilton.

  11. - Estimated Mileage: 34

    Little Bay – Montserrat

    anchorage

    HIGHLIGHTS

    Overnight Stop: Anchor at Little Bay on the northwest corner of the island. Montserrat’s Soufriere Hills volcano erupted in 1995, causing significant damage to the south end of the island and leading to the creation of an exclusion zone. The north end of the island is largely unaffected, and has black-sand beaches, coral reefs, cliffs and shoreline caves. The still active volcano is the island's stellar attraction, and the only live volcano in the Caribbean that you can observe at close quarters in safety. The lush, forest Centre Hills is renowned for its biological diversity. The rainforest is well known for bird watching the many species of resident land birds and migrant songbirds that inhabit the area.

  12. - Estimated Mileage: 30

    Nelson’s Dockyard Marina

    St. John's, St. John's

    268-460-7976

    HIGHLIGHTS

    Overnight Stop: Dock stern to in the historic restored Nelson’s Dockyard. Visiting the museum, art galleries, shops and restaurants is a fine way to spend the day. Watch sunset from the old British military complex atop Shirley Heights. Partake in the barbecue party and steel band performances there every Sunday night.

  13. - Estimated Mileage: 11

    Brown’s Bay – Antigua

    anchorage

    HIGHLIGHTS

    Overnight Stop: Nonsuch Bay on the eastern coast of Antigua is a reef-protected body of water that is wonderful for gunkholing. Anchor in Brown’s Bay off the ruins of the Harmony Hall mill. Harmony Hall is now a boutique hotel with one of the best Italian restaurants in the Caribbean.

  14. - Estimated Mileage: 55

    Marina Bas du Fort

    Pointe a' Pitre, Guadeloupe

    011-590-590-93-6620

    HIGHLIGHTS

    Overnight Stop: Dock in the large protected harbor near downtown of Guadeloupe’s most important city. Take a walking tour of downtown and visit both Musee Schoelcher and Musee Saint-John Perse. The downtown has a fascinating creole atmosphere, and La Darse is a busy waterfront market.

  15. anchorage

    HIGHLIGHTS

    Lunch Stop: Anchor off the town and dinghy ashore for a walk through this adorable seaside fishing village. Have lunch at one of the handful of local restaurants.

  16. - Estimated Mileage: 1

    Anse a Cointe

    anchorage

    HIGHLIGHTS

    Overnight Stop: Anchor behind Pain de Sucre, a 200-foot high outcrop joined to the island by a low strip of land with beautiful beaches on both sides. This is a picturesque and quiet anchorage.

  17. - Estimated Mileage: 20

    Prince Rupert Bay

    anchorage

    HIGHLIGHTS

    Overnight Stop: Anchor off the beach a little to the north of town, it is the calmest area if there is any northerly swell. It is a short walk into Portsmouth and nearby Cabrits National Park. A taxi ride to spend the afternoon at Kalinago Territory on the windward side of the island is fascinating. This is the cultural preserve of the Caribs, the last remaining indigenous people of the Caribbean. Visit a traditional village and learn about the Carib crafts and heritage.

  18. - Estimated Mileage: 20

    Roseau

    anchorage

    HIGHLIGHTS

    Overnight Stop: Pick up a mooring ball just south of town off the Anchorage Hotel. Dominica is largely covered by rainforest and is home to the world's second-largest boiling lake. The island has many waterfalls, springs, and rivers., and promotes ecotourism. The volcanic nature of the island and the lack of sandy beaches have made Dominica a popular scuba diving spot. This island has many excellent diving spots due to its steep drop-offs, healthy marine environment, and reefs. Roseau is the island’s capital and is the best location to arrange tours of the island.