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January 7, 2022

Sailing Itinerary for the Leewards

Plane landing in Saint Barthelemy famous airstrip

Located on the edge of the northeastern Caribbean Sea as it joins the Atlantic Ocean is the scenic collection of tropical islands making up the Leeward Islands archipelago. A part of the broader Lesser Antilles, the Leewards include the US and British Virgin Islands, Anguilla, Saint Martin, Saint Barthélemy, Saba, St. Eustatius, St Kitts, Nevis, Antigua, Barbuda, Redonda, Montserrat, and Guadeloupe. While the Leeward Islands are situated relatively close together, they are scattered in such a way that there is no logical linear route. Therefore there are many itinerary options and this particular one allows for the relaxed pace of a sailing yacht with a little time to explore each of the stops.

Your yacht charter vacation will begin in Simpson Bay on the Dutch side of St Maarten. If arriving via plane, you will seemingly skim over the bay as you land at Princess Juliana International Airport. There you will be met by your charter crew and taken to board your home away from home for the next week. After a welcome aboard cocktail and getting situated in your cabin, you will sail a short distance north to the French side and anchor in Marigot.

The marina of Marigot in Saint Martin on the French side of the Caribbean Island.

Day 1: Marigot is the capital of the French portion of Saint Martin and represents European and Caribbean cultures. Very close to your harbor anchorage are open-air shopping stalls, duty-free shopping, al fresco dining, boutiques, and colorful Creole architecture. With many sights to see and wonderful open-air cafes, spend the evening exploring, enjoy dinner ashore then head back to your yacht for a peaceful night.

Beautiful beach framed with palms and seaside cafe on Caribbean island of Anguilla

Day 2: The next morning you will awaken to the smell of freshly baked croissants, and after a delicious continental breakfast, you will sail three hours north to the gorgeous shores of Anguilla. There is so much to enjoy in this laid-back paradise that you will spend two nights enjoying the beaches, the turquoise sea, and the hospitality ashore. The first evening, you will anchor in peaceful Crocus Bay where you can swim and snorkel off Pelican Point. After a day of enjoying the water, you will be served an amazing dinner of grilled seafood on deck as you watch the brilliant sunset.

Day 3: This morning you might choose to go ashore and explore or enjoy a relaxing morning on deck as you sip your coffee and savor the view. After lunch, the crew will pull up anchor and head to Prickly Pear Cays for an afternoon of sun and fun before continuing east to spend the night anchored off uninhabited Scrub Island. Before imbibing in sundowners, you might swim, kayak or dinghy to the beach at Windward Point Bay, and possibly hike over to the ruins of an old hotel and plane crash site, representing a piece of the island’s colorful history. Depending on when you are there, you might be fortunate enough to observe whales off the southern coastline.

Anse Marcel beach and boats on french side of St Martin

Day 4: As you continue your journey, you will depart Scrub Island and sail several hours south to Tintamarre Island off the northeastern coast of St Martin. There are many gorgeous natural beaches on this uninhabited Nature Reserve as well as superb snorkeling and diving sites, including a shipwreck on the western side. You might also wish to hike inland a bit to plunge in and take a mud bath. After a wonderful day enjoying the surf and sand, you will return to the yacht for another delicious dinner under the stars.

Saint Barthelemy skyline and harbor in the West Indies of the Caribbean.

Day 5: You will rise and shine early this morning for a day of sailing as you make your way to Gustavia, St. Barths. Known as the Riviera of the Caribbean, Saint Barthélemy is a yachting dreamland. Once you have moored, spend the rest of the day ashore taking in the exotic beaches, exciting water sports, fascinating history, wonderful spas, high-end duty-free shopping, locally made jewelry and crafts, exquisite French restaurants, and glittering nightlife. This glamorous port of call is one of the highlights of any Leeward Island itinerary.

Day 6: Depending on your preferences, you might spend the morning continuing your tour of bustling Gustavia, or make the short sail northwest past the Rockefeller Mansion to tranquil Colombier to snorkel, kayak or look for dolphins off the point. After lunch on the yacht, you will head downwind to Ile Fourche as you make your way back west. Spend the afternoon hiking to the top of one of the islands’ five summits for a spectacular view of the Leeward Islands, or snorkel among the sea turtles. After the excitement of St. Barths, tonight you will enjoy a relaxing dinner, grilled and served on the deck of your chartered yacht, followed by cocktails served under the star-filled sky.

Anse Marcel beach on french side of St Martin Sint Maarten Caribbean

Day 7: Today you will sail back to Saint Martin to one of the most beautiful anchorages on the island, Orient Bay. For the final full day of your charter vacation, you have a variety of options in Orient Bay. There is a wide white sandy beach and a wide range of water sports, as well as a secluded island cay and a clothing-optional beach. The bay is also lined with an extensive selection of restaurants, from local causal eateries to gourmet fine dining alternatives. After sunset, the village square livens up with local musicians and lots of tropical cocktails. Tonight is a time to celebrate the memories you have made on your amazing yacht charter holiday before being gently rocked to sleep at anchor for one last night….until next time.

Day 8: Depending on your schedule, you might stop off in Philipsburg for a last bit of duty-free shopping before returning to Simpson Bay. If you are catching a flight this afternoon, you are very close to the airport. If you are fortunate enough to stay a little longer, take time to explore more of the delights of this small two-nation island.

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Category: St Barts, St Martin, Yacht Rental Destinations
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