Turn Your Dreams Into Experiences

Let your personal Waypoints™ charter reservation manager deliver truly personalized, full-service charter vacations from the finest sailing destinations in the Atlantic and Caribbean. Waypoints™ offers an independent, boutique charter experience, managed by local owners who know the best sailing waters and hidden gems of their home base.

The yachts available for charter at each Waypoints™ location are new-model, privately-owned Jeanneau yachts and Fountaine Pajot catamarans.

Jeanneau Fountaine Pajot

Charter options include Bareboat, Skippered, All-Inclusive and Instructional Charters.


  • Abacos, Bahamas
  • Annapolis, MD
  • British Virgin Islands
  • Cape Coral, FL
  • Exumas, Bahamas
  • Grenada
  • Key West, FL
  • Newport, RI
  • St. Petersburg, FL
  • US Virgin Islands

Reserve Your Charter

Boundless Destinations

Experience the beauty and lifestyle of the Chesapeake, or set sail from one of our affiliated locations. We provide the same world-class charter experience from a host of destinations, managing the entire process for you and ensuring a relaxing and enjoyable trip. Explore locations up and down the Atlantic Coast and Caribbean.

See Destinations