Waypoints® offers boutique charter experiences in the world’s best cruising destinations.

tropical island

About Waypoints


When you set out for the finest sailing destinations in the world, you deserve a personally-crafted yacht experience managed by local charter specialists with local knowledge of secret anchorages, quiet spots, and not-to-miss experiences. You deserve Waypoints®.

Waypoints® offers boutique charter experiences in the world’s best cruising destinations. Yachts available for charter are new or late model, privately owned, and professionally managed, including the best from world-class manufacturers, such as Fountaine Pajot and Jeanneau. Our yachts are outfitted for maximum comfort and performance, not mass-market charter. Charter options include Bareboat, Skippered, All-Inclusive and Instructional Charters. 

We are looking for new yachts to join our fleets. Now is your chance to own a new yacht for far less than you ever imagined. Waypoints® works in conjunction with the Business Yacht Ownership® program, offering owners the flexibility to keep their yacht in any of our locations with income and tax advantages to offset costs. Yacht sales are through Atlantic Cruising Yachts, the originator of the Business Yacht Ownership® program, and a worldwide leader with over 35 years of experience and over 1,000 participants to date.

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Boats & Rates

Boat Lengths:   

 37’-67’ Feet

Boat Types:  

Sailing and Power Catamarans and Monohulls

Charter Types:   

 Bareboat, Captained, All-Inclusive, Crewed Charters, and ASA Sailing Instruction

  • yacht in the water
  • man and woman on a yacht drinking cocktails
  • people sitting on yacht in the ocean

Charter Destinations

Locations in the Virgin Islands, Bahamas, Belize, Florida, New England, and the Chesapeake Bay

woman kayaking

Contact Us

 312 Third Street

Suite 101

Annapolis, Maryland 21403   

Phone:  443.225.4355        

Email: info@waypoints.com      

Website: waypoints.com    

Social Media: Facebook | Twitter | Instagram

Special Offers  

Can be found online at waypoints.com

Ready to Plan a Charter?