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Discover Diverse Sites in Our Leeward Islands Itinerary

The Leeward Islands are nothing if not diverse. The one common denominator is the raw beauty of the region – think turquoise water, ultra-white sand beaches, and sunsets that will make you want to never return home.

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Day 1 - Saint Martin

Your charter adventure will begin in the legendary Simpson Bay in St. Martin, a gorgeous island comprised of a Dutch side, Sint Maarten, and a French side, St. Martin. The capital of Sint Maarten, Philipsburg is world-renowned for its shopping. The French side is equally well-known, perhaps unsurprisingly, for its fantastic cuisine. Enjoying both sides on Day 1 is a terrific way to kick things off in the Leewards!

Day 2 - St. Barths

St. Barths is celebrated for its extraordinary French cuisine, high-end shopping, and overall decadent lifestyle – so what better stop for the second day of your charter experience? In the last few decades, St. Barths has joined the ranks of celebrity & billionaire hot spots, and, if you haven’t already been there, you’ll soon find out why it’s become such a popular location amongst global elites.

Nikki Beach for afternoon cocktails, or perhaps finding an unbelievably scenic spot on the water at Anse de Grande Saline, one of St. Barths most highly acclaimed beaches, is what we would highly recommend for the day. Eden Rock hotel for a sumptuous meal and delectable drinks would be our “go-to” move for the evening – that said, your captain & crew might have some stellar ideas too, so it’s best to keep an open mind!

Day 3 - St. Kitts

If you’re a fan of the outdoors, then St. Kitts will be right up your alley. This breathtaking island boasts tropical rainforests, as well as plenty of hiking & diving opportunities. We’d recommend heading over to Brimstone Shallows, where you’ll see all of the tropical fish you’d ever want to see (not to mention the occasional reef shark), for some world-class scuba diving. Mount Liamuiga is another treat – this stratovolcano, which tops out at 3,792 feet, is one of the highest-altitude spots in all of the Caribbean. You won’t believe the view!


Any golf lovers in your charter party will want to head on over to Royal St. Kitts Golf Club, an 18-hole championship course. On the other hand, if what you’re really looking to do is achieve complete & total relaxation, then we’d suggest making a trip to Emerald Mist Spa. You won’t be disappointed. And f you’re feeling lucky, the casino at the St. Kitts Marriott Resort is a wonderful place during the evening.

Day 4 - Nevis

The virtually untouched island of Nevis is a quick trip from St. Kitts, and well worth the visit. Nevis is well known for its wild Green Vervet Monkeys, and a plethora of other wildlife. That’s what’s so alluring about this island. Nevis provides an opportune time to enjoy some (or perhaps all) of the water toys on board your yacht. The fishing here is first-rate too. Then again, we’d also put a plug in for Lovers Beach, which is as nice a place to get away & relax as any we have seen. But we’re torn – after all, the hiking, biking, and horseback riding on Nevis is also incredible.

Day 5 - St. Eustatius (Statia)

St. Eustatius, which is often (quite affectionately) called Statia, is tiny. But this former Dutch province makes up for its size with over-the-top snorkeling & diving opportunities. There are more than enough coral reefs and ship wrecks around Statia to keep everyone from amateur to professional divers entertained. If dramatic-looking extinct volcanos are your thing, then Quill is the ideal place for a hike. There are plenty of guides to show your around.

Day 6 - Anguilla

The second-to-last day of your charter experience is an ideal to enjoy a laid-back day on Anguilla. The beaches and beach bars are among the best in the Caribbean on this island. If you & your guests want to step it up in the activities department, then we’d recommend indulging in some of the terrific golfing that’s available on Anguilla. There’s also tons of good restaurants on the island. Anchoring for the night in Rendezvous Bay is a wonderful way to close things out.

Day 7 - Back to Saint Marten

Enjoying downtown Marigot, and the markets there, are a perfect way to cap off what will have been an exhilarating week. Hiking up to Fort Louis, which overlooks Marigot Bay, is another great option if you’d like to keep things up-tempo until the very end.

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