Updated: May 12, 2021
Why not start your Caribbean sailing holiday from St. Martin, spin around Anguilla and St. Barts and then come back for more next year?
First things first... in case you've heard of Leeward Islands but are not sure where they are, here is the shortest explanation we can give: Leewards are a cluster of islands in the Caribbean Sea. They include Virgin Islands, Guadeloupe, Antigua & Barbuda, St. Kitts & Nevis, St. Martin & Anguilla and a number of smaller islands.
This time, we are giving you a slice of these heavenly sailing grounds that many have claimed and coveted. We will start our journey by flying to St. Martin. Even if you have never heard of this island, you have seen many photos of airplanes flying low over the crowded beach. Well, that's St. Martin (as it is called on its north, French side or Sint Maarten as it is called on its south, Dutch side.
Our favorite charter base in Port De Plaisance Yacht Club, often described as 'the most elegant marina in the Caribbean' and only some 10 minutes taxi ride from the airport. This is a full service facility with a brand new, well stocked supermarket near by.
Once you have gotten acquainted with your charter yacht and settled in, we recommend that you spend your first day sailing around the Marigot Bay and spend some time on the Marigot waterfront. Marigot is the capital of the French side of St. Martin. Its attractive waterfront is dotted with shops, restaurants and casual eateries, all offering varied and high end French cuisine. You will also find abundance of vibrant and lively bars, often with live entertainment.
It's important to note that there are no moorings available but the anchorage south of Marina Fort Louis offers plenty of space and excellent holding. You can use your dinghy to get ashore as dinghy docks are available.
From Marigot you could easily hop over to Anguilla island and drop your anchor at Road Bay. Road bay is one of the nicest anchorages in the northern Leewards and more than well worth visiting. There are no moorings but plenty of room to anchor, with good holding. The whole Anguilla island is laid back and very unassuming which greatly adds to its appeal. If you wish you can spend some time on a pristine white sandy beach which runs along the shoreline of Road Bay or visit any of the numerous casual dining restaurants and vibrant bars. You will need your dinghy to bring you from your yacht to the dinghy dock.
There are many other things you can do in Anguilla, snorkeling and diving being probably the most popular. Anguilla is a wreck dive capital of the world and you can book a guided tour to make sure your don't miss anything.
Another one of our favorite spots in Anguilla is Crocus Bay. There you will find a very peaceful and well secluded anchorage with steep cliffs rising 70ft high from the white sandy beach. You can drop your anchor south of Pelican Point for best holding and use your dinghy to get to the beach.
The Valley, Anguilla's main settlement is within short walking distance from Crocus Bay. Should you choose to venture there, you will find excellent restaurants, shops and art galleries.
From Crocus Bay, you should head to the north-east coast of St. Martin and anchor in Orient Bay. We recommend either of the two anchorages - to the west of Ille Pinel which is snug and quiet with good holding or west side of the Green Cay which is a lot livelier but also with excellent holding.
Ile Pinel is dotted with beach side shacks where you can rent windsurfing and other water sports equipment. Snacks and soft drinks are available, and you can arrange a ride in an ultralight aircraft for mind blowing views and photos for your Instagram. You will find a few restaurants and shops within walking distance of the dinghy docks.
On Green Cay, nude sunbathing is popular on the eastern stretch of Orient Beach. Windsurfing and other water sports rentals are available. There are many restaurants on the waterfront and provide a good place to enjoy a lively atmosphere.
After all that excitement, it's time to sail south-east to the western tip of St. Barts and drop your anchor at Anse de Colombier. You will find wide variety of yachts anchored in a horse-shoe shaped bay surrounded by steep hills. Here you will have a choice between free moorings or dropping your anchor. If you choose the latter, holding is good. There are no dinghy docks so if you decide to go ashore, you will need to beach your dinghy.
Snorkeling is popular in the bay. The rocks surrounding Ile de la Pointe, are our favorite spot for snorkeling and scuba diving. South of that is an inlet where sea turtles and sea rays are sometimes observed.
After all that peace and quiet, you may be ready for Gustavia, the main port of entry to St. Barts, on it's south side. The harbor is well protected should you choose to anchor. Alternatively, moorings are available for a fee.
The boutiques and restaurants are the main attraction of Gustavia, apart from its picturesque town and wonderful French culture. A hike up the hills to the lighthouse at Fort Gustav is well worth it for the views. You can also climb the steps up Fort Karl.
Since we are getting close to the end of our week long sailing holiday, it's time to head back to St. Martin. We suggest that you head to the Great Bay. Philipsburg, the capital of the Dutch side of Sint Maarten is located there. There you will find all the facilities you need, including marinas, restaurants, shops, casinos and plenty of night life. You can anchor off the breakwaters of the inner harbor, clear of the big cruise ship docks.
With such a wide variety of things to do, you may want to spend more than just one day or one night in the Great Bay, if you have time.
Once you are done with Philipsburg, you can head back to Port de Plaisance for the end of your charter. You will need to get there the afternoon before disembarkation day.