Waypoints®

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

About Waypoints®

When you set out for the finest cruising 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. Yachts available for charter are new or late model sailing and power monohulls and catamarans, from world-class manufacturers such as Fountaine Pajot and Dufour. Each yacht is privately-owned, meticulously maintained, and outfitted for comfort and performance with generators, air conditioning, water makers, high-quality linens, galley equipment, and more. 

Boats & Rates


Boat Lengths:   

37’-67’ Feet


Boat Types:  

Sailing Catamarans, Sailing Monohulls, Power Catamarans, and Powerboats (Monohulls)


Charter Types:   

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


Charter Destinations

  • Annapolis, Maryland 
  • British Virgin Islands
  • The Bahamas
  • Belize
  • Kemah, Texas
  • Newport, Rhode Island
  • St. Petersburg, Florida
  • U.S. Virgin Islands 

Contact Us

Waypoints Yacht Charters

312 Third Street

Suite 101

Annapolis, Maryland 21403


Phone: 443.225.4355

Email: info@waypoints.com      

Website: waypoints.com    


Social Media: Facebook | Instagram

Ready to Plan a Charter?