Aerial view of Sandy Cay, British Virgin Islands

Charter in the
World’s Best Destinations

Elevate Your Charter Experience

A group of friends jumping into the water from the stern of a yacht

Discover the World’s Best Destinations

Cruise in the most beautiful waters of the world with Waypoints® Yacht Charters.

Discover Our Locations
A man and woman enjoying lunch on a yacht

Choose the Perfect Charter Type

Ranging from bareboat to all-inclusive, our charter specialists will work with you to find the best charter type.

Charter Your Way
A sailing catamaran anchored offshore

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.

View Our Fleet

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.

A family posing for a picture with the British Virgin Islands in the background
Norman Island, British Virgin Islands

An Insider’s Viewpoint

An Incredible Experience

“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.
Thomas Point Lighthouse at Sunset
Thomas Point Lighthouse

Destination Spotlight

Waypoints® Annapolis

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.

A man and woman in a powerboat on an open body of water
Cape Coral, Florida

Yacht Ownership is Closer Than You Think

The Smartest Way to Own Your Yacht
Business Yacht Ownership graphic

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.