Annapolis Sample Itinerary

The Waypoints Annapolis base is in the heart of Annapolis right in the middle of the sailing capital of the world. The Chesapeake Bay, at about 200 miles long, is the largest estuary in the United States. There are coves and inlets all along the shoreline, small quaint towns to explore, and plenty of places to anchor or dock with history all around you as you explore national landmarks.  

Your destinations on the Chesapeake Bay are boundless. Make sure to allow time to visit downtown Annapolis at the beginning or end of your charter. Here you will find Main St. and small side streets loaded with shops, restaurants, galleries, and the Market House. And if time allows, take a stroll through the Naval Academy. Whatever you choose, you cannot go wrong in this historic town. 

Sailing Itineraries are helpful when planning your charter. You can choose the North or the South route. North takes you to historic Baltimore Harbor with nice quiet anchorages along the way. Sailing the South route will take you to places such as the legendary St. Michaels and the historical landmarks in Oxford and Cambridge. 

So many destinations on the Bay to explore makes Annapolis a great choice for your charter vacation.