Charter in the
World’s Best Destinations
Elevate Your Charter Experience
Discover the World’s Best Destinations
Cruise in the most beautiful waters of the world with Waypoints® Yacht Charters.
Choose the Perfect Charter Type
Ranging from bareboat to all-inclusive, our charter specialists will work with you to find the best charter type.
Explore Our Fleet of Sail and Power Yachts
Our large fleet of award-winning luxury monohulls and catamarans are fully equipped to exceed your expectations.
Contact a Charter Specialist to Learn More
Our charter specialists know the best sailing and cruising waters, local life, bars, and other hidden gems unique to their destination — creating the most memorable experiences on the water. Speak with a charter specialist directly for assistance in crafting the perfect charter vacation.
An Insider’s Viewpoint
“It was our first time chartering a boat and we had an incredible experience. Working with Waypoints® made the whole process super simple. Susan was very knowledgeable on the Virgin Island area and the boat that would best fit our family’s needs. I wouldn’t charter a boat any other way. Thank you!”Ben B.
The Chesapeake Bay is among the world’s top cruising destinations and the world’s largest estuary. The Bay offers over 5,000 miles of navigable, protected coastline with an incredible diversity of cruising potential. From quiet, pristine anchorages, to historic seaside villages, to the busy ports of Baltimore and Annapolis, the Bay offers something for everyone.
Yacht Ownership is Closer Than You Think
We are looking to grow our fleet of award-winning new model yachts. Learn about Business Yacht Ownership® and how it’s possible to offset a substantial portion of new yacht costs with income, special financing options, and potential tax advantages.