Exclusive Charter Specials

A Trifecta of a Deal!


  • Book a charter vacation at one Waypoints base and save 5%
  • Book a charter vacation at a second Waypoints base and save 10%
  • Book a charter vacation at a third Waypoints base and save 15% PLUS get 3 free nights.

Our charter specialists can assist you with planning the perfect charter vacation at one, two, or all three Waypoints® Yacht Charter bases.

*Must book your first charter by August 15, 2021 and subsequent charters within 18 months. Additional restrictions apply. Contact your charter specialist for complete details.

Annapolis Specials


Girl’s Weekend on the Bay

Need a weekend out with the girls? Book a charter and experience all the Chesapeake Bay has to offer! The first 5 people will save 20% on your upcoming charter! 

A weekend getaway in Annapolis is exactly what you and your friends need. When you step aboard your private yacht, a chilled bottle of champagne will be waiting for the first toast of your weekend. A water taxi can take you into historic Annapolis where after shopping, you’ll eat at some of the finest restaurants the Chesapeake region has to offer. The next morning, sail over to St. Michaels for a starry night on the hook or head ashore for a night out of fun.

*New​ and direct bookings only. Cannot be combined with any other offers. Not valid for day sails. Contact Waypoints Annapolis® for more information and to book your charter.