7. St. Martin
St. Martin is located in the beautiful Caribbean Sea and is one of the most popular sailing destinations on the planet. The island is effectively ruled half by France and half by The Netherlands, so you get two cultures in one compact destination. The Dutch refer to the island as St. Maarten. The site of great sailing regattas, St. Martin is also home to world-famous beaches, resorts, restaurants, nightlife and enchanting tropical scenery. You can also visit nearby Anguilla, St. Barts and Saba. If you’re seeking a dream Caribbean escape, this is one of the best places to charter a yacht.

8. Maldives
The remote Maldives are a far-flung destination, but don’t let the distance prevent you from experiencing these breathtaking isles. There are more than 1,190 small coral islands in this Indian Ocean chain for endless island hopping options. Yacht enthusiasts can enjoy water sports as well as beach combing during their visit here. Start your charter on the main island of Male, then set off to explore some smaller fishing villages and uninhabited atolls.

9. Chesapeake Bay
Historic Chesapeake Bay is considered by many to be the sailing capital of the world. This eastern American waterway is the largest estuary in the U.S. with miles and miles of shoreline to explore. During your voyage, you can puruse the historic James River and drop anchor in historically important cities like Richmond, Annapolis and Baltimore. If you prefer natural settings, there are many islands in the bay that are known for their pristine charms. The protected waters of Chesapeake Bay are ideal for novice sailors, but experienced skippers will also enjoy this region.
