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Leeward Islands

A boy is standing on the bow of a sailboat.
A boy is standing on the bow of a sailboat.
A man standing on a hill overlooking a harbor.


For nearly 350 years, the French and the Dutch have politely shared this paradise and somehow managed to maintain their cultural clarity. The French side offers luxury resorts, high fashion, fine dining, and beautiful beaches. The Dutch side is a busy commercial area bustling with trade and tourism. We’ll make landfall at Philipsburg, the busy capital of Dutch St. Maarten and clear customs and enjoy a bit of shore time.

A group of people hiking through the jungle.


It’s a beautiful sail to Oranjestadt where we’ll pick up a mooring ball on arrival. Excited to see more of the Leewards our first stop might be the historic Fort Oranjestadt. It’s a great time walking the ruins and learning more about the island. We’ll also make the arduous Quill hike which takes us through the rainforest and up to the rim of the island’s extinct volcano. One SC group even saw a tarantula on their trek back down, making their expedition complete.

Two people standing on a wooden platform in the ocean.


After anchoring at Pinney’s Beach last summer, we went ashore and set up each crew member with a bike and helmet. We then set off as a pack to explore Nevis. The gorgeous ocean views and lush green vistas kept us occupied on the hour long cycle into Charlestown. In town, we stumbled upon a local fruit festival where the crew enjoyed food from stands and music in the town square. After pedaling back and returning our bikes, we cooled off with a swim and chilled on the beach before dinner.

A boat in the water with a rope attached to it.


From the docks in Basseterre, St. Kitts get ready for our taxi tour of the main town as well as some of the island’s historical sites including Bloody River and Fertility Rock. Hiking through a lush rainforest and the chance to swing from a jungle vine is always a highlight. But the botanical garden, batik factory and Fort George with panoramic views of lush volcanic hills are amazing too. A cool swim at Shipwreck Beach feels so great after a busy day of island exploring.

A person walking down a path in the jungle.


Visitors to Saba get to hike through the clouds and visit the summit of Mt. Scenery. This island is the highest point in the Netherland Antilles, and its picturesque villages seem to cling to clefts in the rock. A taxi ride up the mountain brings you to Saba’s main town called “The Bottom”. An artistic glass bead studio, the gubernatorial mansion, and Wilhelmina Park are worth exploring. Ambitious visitors can walk down the 400 steps to Ladder Bay to enjoy a nice swim and relaxing picnic. We will take time out to snorkel and dive as Saba offers some of the most remarkable diving in the Caribbean.

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