Annapolis Sailboat Show
Step Aboard with Waypoints at the Annapolis Fall Sailboat Show
Join Waypoints Yacht Charters at the Annapolis Fall Sailboat Show, October 15–18, at the Vacation Basin, Annapolis City Dock. Come step aboard two stunning yachts from our fleet and see firsthand what a Waypoints charter vacation feels like:
Meet Betty
Dufour 44
A sleek, performance-driven monohull built for comfortable, confident sailing.
Meet Serenity Now
Fountaine Pajot 42
A spacious, luxurious catamaran designed for effortless cruising and relaxed entertaining on the water.
Our team will be on hand to answer questions, share our favorite Chesapeake Bay itineraries, and help you start planning your next adventure — bareboat, captained, or all-inclusive. Stop by, step aboard, and see why Waypoints is the smarter way to charter.