As your sailing holiday begins, you start by traveling to Orient Bay to port. Hidden behind two cays, lies the entrance where you are able to enjoy lunch. A little further north is Tintamarre, another nice port, with both areas offering great beaches. Grand Case Bay is usually a pleasant anchorage for the night as it is home to a wide selection of good restaurants and lively bars. It is also home to Creole Rock, which offers superb snorkeling adventures. The port of Marigot is always bustling so if you’d like, you can anchor there and enjoy the nightlife.
A lower island known for its scuba diving, restaurants, and laid-back Caribbean charm, Road Bay is one of the most pleasant areas in northern Leeward Islands. Furthermore, serving as a port for cruising yachts, it is a great place to go ashore for dinner. Not far away is Sandy Island, one of the many off-lying areas in Anguilla that is protected as a marine reserve. Sandy Island is a good choice for an afternoon spent swimming or snorkeling.
Next stop leads you out to Prickly Pear Cays, part of Anguilla’s marine park. These tiny islands offer a good lunch stop in warm weather perfect for a swim or snorkeling along the reef. If you anchor off the south side of East Prickly Pear, you’ll get the chance to see seabirds nesting in the craggy cliffs, a pristine white-sand beach along the cay, and the dazzling colors of the ocean. Go ashore along the north side of the island, enjoy a stroll while listening to the “whistling rocks” as they fall in rhythm with the waves. Going back to the main island will take you to scenic Crocus Bay where you can anchor for the night and explore.
You may have stopped for lunch here on your first day of your sailing holiday in St. Maarten. It definitely warrants a longer stop as Orient Bay offers two good anchorages, shore side attractions, and plenty of watersports to pass your time.
Next up, you travel to one of the prettiest locales in the Northern Leewards, St. Barts, officially known as St. Barthemey. On the way, stop for some lunch and snorkeling at the privately owned Ile Fourchue, a small, hilly isle off the coast. The picturesque waterfront town of Gustavia is less than two hours away where you can stop and explore.
Steep hills overlook the blue waters of the picture-perfect bay of this stop. A nearby village is situated and is well-worth the hike as you will get a stunning view of surrounding islands, as well as great opportunities to snorkel, swim, sunbathe, and relax.
Philipsburg, the Dutch Capital of St. Maarten, is a thriving waterfront port with a lively nightlife, interesting shops, excellent restaurants, and casinos. There is also a beach boardwalk lined with restaurants worthy of a stroll before you decide where you want to stop for dinner on the last evening of your sailing holiday in St. Maarten.