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

Waypoints Yacht Charters

About Waypoints®

When you set out for the finest cruising destinations in the world, you deserve an elevated charter experience managed by the best charter experts in the industry. Our boats are held to the highest standards, giving you the feeling of a 5-star hotel when you step aboard. Our team has the knowledge you need to have the experience of a lifetime including secret anchorages, quiet spots, and not-to-miss experiences in each location.

We offer bareboat, skippered, all-inclusive, and instructional charters in the world’s best destinations including the BVI, the USVI, Annapolis, MD, and St. Petersburg, FL. Yachts available for charter are new or late model sailing monohulls and catamarans and powerboats, 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, watermakers, 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

Chantier Fountaine-Pajot, Astrea 42
waypoints charter people drinking
Fleewinter shoot of Yacht Lunous
Waypoints Charter boats on the water.

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: [email protected]      

Website: waypoints.com    

Social Media: Facebook | Instagram