Upcoming Events

2023 Annapolis Boat Show

Annapolis Sailboat Show (U.S. Sailboat Show): October 12 – 15, 2023 | Annapolis, MD

The Waypoints Team is pleased to be back in Annapolis for the 2023 Fall Boat Shows! Visit our team and book your 2023-2024 charters in the world’s best sailing destinations from our growing fleet.