Waypoints®

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

About Waypoints®

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


Waypoints® offers bareboat, skippered, all-inclusive and instructional charters 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 Dufour. Our yachts are outfitted for maximum comfort and performance, not mass-market charter.


Additionally, if you’re interested in owning your own yacht, we are looking for new yachts to join our fleets. Waypoints® works in conjunction with Business Yacht Ownership®, offering owners the flexibility to keep their yacht in any of our locations with the opportunity to offset 80-100% of the costs through income, special financing, and potential tax advantages. Yacht sales are through Atlantic Cruising Yachts, the originator of the Business Yacht Ownership® program, and a worldwide leader with over 40 years of experience and over 1,000 participants to date.

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


Charter Destinations

  • British Virgin Islands
  • U.S. Virgin Islands 
  • Bahamas
  • Belize
  • Croatia
  • Key West, Florida
  • St. Petersburg, Florida
  • Annapolis, Maryland
  • Kemah, Texas
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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?